SUBJECT INDEX*

Italicized configurational prefixes (as glycero-) are used as main entries, whereas other italicized prefixes (as scyllo-) are listed under the stem name. A Acetoacetic ester, 240 Absolute configuration, 15 synthesis of DL-mannitol, 250 Acacia species, 685, 510 reactions with sugars, 240 gum arabic, 685 Acetobacter species, Acetaldehyde, see also Ethylidene de- A. acetigenum, 708 rivatives, 235 cellulose synthesis, 708 Acetals, see also Alkylidene derivatives, A. suboxydans, 98, 133, 365 individual aldehydes and ke- action on inositols, 282 tones, individual sugars, and preparation of Anhydro sugars, 1,6-labeled ketoses, 136 acetal type, 227 planteobiose, 501 alkali labile, 390 A. xylinum, 98, 102, 132, 365 definition, 188 cellulose synthesis, 707 preparation, 157, 288 Acetohalogeno sugars, see O-Acetylgly- Acetamide derivatives, 408 cosyl halides; also Acetates and Acetates, see also Acetylation, Es- individual sugars ters, Esterification, Orthoace- Acetolysis, tates and individual compounds, anhydro compounds, 394 139 anhydro sugars, acetal type, 223 ΑΓ-acetyl groups méthylène groups, 232 hydrolysis, 650 polysaccharides, 702 resistance to alkali, 463 Acetone derivatives, see Isopropylidene acetyl migration, 147, 408 Acetylation, see also Acetates, Ortho- acyclic, 139, 142, 144 acetates, and individual com- aldehydo, 139, 142 pounds, 139 anomerization, 141, 483, 495 aminodeoxy sugars, 471 distinction between N- and O-acetyl anomeric ratio, conditions affecting, 140 as analytical procedure, 140 groups, 410 catalysts, 139, 140, 692 enhancement of rotation (alditols), 260 effect of pH on rate, 140 furanose, 141 glycosylamines, 408 keto, 139, 144 tautomers, 140 polysaccharides, 692 Acetylene, estimation of hydroxyl groups, 648 synthesis of alditols, 242, 244 preparation of aryl glycosides, 198 ethylidene compounds, 235 pyranose, 139 β-N- Acetylglucosaminidase, replacement of anomeric acetate alfalfa emulsin, 590 byhalide, see O-Acylglycosyl halides almond emulsin, 577 by nitrate, 169 O-Acetylglycosyl halides, 150 septanose, 146 formation of anhydro sugars, acetal Acetic acid, labeled, degradation, 624 type, 222 * Subject Index compiled by James Achromycin, 465 W. Pratt. Achroic point, 681 851 852 SUBJECT INDEX

Achroic R-value, 681 synthesis, 151 Acids (mineral), see also 2-Furaldehyde, synthesis of, Levulinic acid, Anhydro sugars, 1,2-glycoseens, 402 acetal type, and individual glycosides, 197, 552 sugars aryl, 190 condensation (polymerization) reac- aryl, thio-, 555 tions, 59 glycosylamines, 416 dehydration reactions, 57 nucleosides, 429 glycoside formation, 59 oligosaccharides, 483 "reversion", 60 thiocyanates, 416 Acids, Organic, see also Aldonic, Aldaric, O-Acylglycosyl phosphates, 174 Uronic and individual acids Acyl halides (Aldonyl halides), 144, 309 peroxy acids, 360 reduction to aldehydo sugars, 144 oxidation of Adenine, 425 glycals, 400 nucleosides, 424 thioacetals, 360 Adenosine (D-Ribosyl-N-adenine), 84, Acofriose, 553 425 diphosphoric acid (ADP), 435 Acorn, 274 synthesis, 436 Acovenose, 553 triphosphoric acid (ATP), 435 a-Acritol (see DL-Mannitol), 250 high energy phosphate bonds, 749 Acrolein dibromide, 103 mixed anhydride formation, 436 a-Acrose, 104 sucrose synthesis (enzymic), 521 phenylosazone, 103 synthesis, 436 reduction, 250 Adenylic acid, 431 Acrylonitrile, Adhesives, 678 cyanoethylcellulose, 695 Adonis vernalis, 246 *'Active glycolaldehyde,,, 770 Adonitol, see Ribitol acceptors, 771 Aerobacillus macerans, 681 donors, 770 cyclic dextrine, 681 Acyclic sugars, see also aldehydo and Aerobacter species, keto sugars, 226 A. aerogenes, 620 O-Acylhalogeno sugars, see O-Acylgly- A. levanicum, 530 cosyl halides levan-sucrase, 706 Acyl migration, 175, 408 Agar, 88, 90, 685 O-Acylglycosyl fluorides, structure, 685 epimerization, 482 use, 686 O-Acylglycosyl halides, see also Ace- Agarobiose, 511 tates, Benzoates and individual Aglycon; aglycon group, 190 sugars, 150, 153 Alanine, N-D-glucosyl-, 447 acyclic, 157 Alcian Blue 8GS, histochemical use, 634 addition to anhydro sugars, 485 Aldaric acids, see also Tetraric, Pentaric, 2-deoxy, 401 etc., and individual acids, 3, furanose, 156 310-14 hydrolysis, 152 as intermediates, 314 ''neighboring group" effect, 153, 157 preparation of dialdoses, 335 reactions with, Aldazimes, 462 amino acids, 447 Aldehyde-ammonia structure (glycosyl- nitrogenous bases, 417 amines), 411 reduction, 383 aldehydo Sugars, relative stabilities, 151 O-acetyl, mutarotation, 145 substitution reactions, mechanism, 153 preparation, 144 SUBJECT INDEX 853

proof of structure, 54 Aldonate esters, 162 reaction with acyl halides, 157 Aldonic acids, 3, 301-310 Schiff reaction, 144 acyl chlorides, 309 Aldehydrols, O-acetyl, 703 reduction, 144 Alditoleens, 405 amides, 308 Alditols, see also individual compounds, 2-amino-2-deoxy, 3, 241-267 epimerization, 472 O-alkylation, 265 preparation, 472 aminodeoxy, 261, 409 as intermediates, 301 formation of anhydro derivatives, benzimidazole formation, 414 378 biosynthesis, 763 preparation, 475-6 characterization of sugars, 301 biochemistry, 266 2-deoxy, 401 biosynthesis, 763 epimerization, 302, 305 chromatography, 265 esterification, 308 "complexes", 262 hydrazides, 309 configuration, 258, 262 hydrolysis, 309 1-deoxy-l-nitro, 476 2-keto, 325 esterification, 261 acid decomposition, 327 etherification, 265 enolization, 326 nitrates, 261 Ruff degradation, 327 nutritional aspects, 796 synthesis, 326 occurrence, 241 5-keto, 325 optical activity, 258 acid decomposition, 327 in aqueous borax, 171 behavior toward oxidants, 326 in molybdate, molybdic acid, 259 synthesis, 326 oxidation, 264 quantitative estimation, 327 qualitative determination, 265 optical rotatory relationships and quantitative determination, 265 "rules", 306 reactions, 261-4 pharmaceutical use, 301 reduction, 265 phenylhydrazide formation, 415 synthesis, 241, 260 polymerization, 305 structure, 258 preparation, 302 use in structural determinations, 258 reactivity, influence of cations, 308 Aldobioronic acids, 318 reduction, 310 hydrolysis, 319 salts, 308 isolation, 319, 669 solubilities, 308 occurrence, 320 pseudo, 319 synthesis, total, 303 Aldolase, 183 thiol esters, reduction, 261 configurations of condensation prod- Aldonic lactones, 304 ucts, 759 epimerization, 305 general reaction, 758 equilibrium with corresponding acid, steric control, 114 304 Aldol condensation, 105, 759 hydrazides, 462 aldolase catalysis, 758 mutarotation, 303, 304 asymmetric catalysts, 114 reactions with alkalies, 308 D-glycerose with dihydroxy acetone, reducing action, 313 113 test for, 308 steric factors, 114 Aldononitriles, 464 854 SUBJECT INDEX

Aldoses, see also Monosaccharides, Su- order of reactivity of hydroxyl groups, gars and individual compounds, 372 24 selective, 371 conversion to ketoses, see also Lobry C-Alkyl compounds, preparation, 117 de Bruyn-Alberda van Eken- O-Alkyl derivatives, see Ethers stein, Glycals, Osones, 134 Alkylidene derivatives, see also Ben- 2-deoxy, preparation, 400 zylidene, Ethylidene, Isopropyl- 6-deoxy, in cardiac glycosides, 553 idene, Méthylène and individual 2-deoxy-2-halogeno, osazone forma- compounds, 229-240 tion, 401 formation, 229 labeled (Cl), 135 in synthesis, 232 quantitative estimation, ring shifts, 230 chloride method, 346 ring size, 230 hypoiodite method, 343, 617 Alligator pear, 101 Kiliani reaction, 618 Allihn method (reducing sugars), 614 Alduronic acids, see Uronic acids Allitol, 252 Alfalfa emulsin, glycosidase system, 590 from D-glueose, 63 Algae, 99 total synthesis, 106 glycerol D-galactoside, 88 Allium species, 520 polysaccharides, 686 Allodulcitol, see Allitol Porphyr a umbilicalis, 94 D-Allose, 24 Algin, industrial use, 687 D-Allopyranoside, methyl, Alginic acid, 687 2,3-anhydro, 168 nutritional aspects, 799 3,4-anhydro, 168 structure, 687 Allyl alcohol, 105 Alizarin, 551 Allyl ethers, polymerization, 369 Alkali, action on, Allyl isothiocyanate, from sinigrin, 554 aryl glycosides, 221 Almond emulsin, 563, 575 polysaccharides, 653 effect of pH on activity, 576 nature of glycosidic linkages, effect on pentosides, 577 determination, 653 enzymes present, 577 sugars, 60-69 ß-glucosaminidase, 473 deep-seated rearrangements, 63 /3-glucuronidase, 596 dependence on cations, 65 hydrolysis of nucleic acids, 426 fragmentation and condensation, 65 preparation and purification, 575 internal oxidation-reduction, 65 Aloe barbadensis, 83 Aloins (cathartic-acting glycosides), 83 lactic acid production, 66 D-Altritol, see D-Talitol mutarotation, 55 D-aZiro-Heptulose (Sedoheptulose), 101, saccharinic acids, 66 259 effect of alkali concentration, 68 action of acid, 102 Alkali number (starch), 649 2,7-anhydro, 102,81 O-Alkylation, see also Methylation, and tetra-O-benzoyl, 81 Triphenylmethylation, 369 enzymic synthesis, 759 alkyl iodide-alkoxide method, in carbohydrate metabolism, 102 sodium, 370 in "pentose pathway", 183 silver, 370 in photosynthesis, 102 thallium, 371 labeled, degradation, 624 alkyl sulfate-alkali method, 369 occurrence, 102 formation of glycosides, 202 7-phosphate, 183 SUBJECT INDEX 855

hexose monophosphate shunt, 770 configuration, 449 metabolism, 771 Elson and Morgan procedure, 650 photochemical production, 753 glycosides, 472 1,7-diphosphate, 183, 772 hydrolysis, 472 preparation, 102 isolation, 469 D-Altrose, 24 nutritional aspects, 797 2-amino-2-deoxy, from D-glucal, 470 occurrence, 465 4-0-0-D-galactosyl, 482 preparation, 391, 468 4-0-0-D-glucosyl, 482 reactions, 471 methyl 2,6-anhydro-a-D-altroside, 375 with amino acids, 448 phenylosazone, 3,6-anhydro, 387 Schiff bases, 471 synthesis, 168, 482 selective deacetylation, 471 Aluminum chloride on acetylated sugars, structure, 466 formation of O-acylglycosyl halides, synthesis, 469 151 Aminopyrimidines, condensation with inversions, 482 sugars, 415 Amadori rearrangement, see also Ami- Amino sugars, see Aminodeoxy sugars nodeoxy sugars and individual Ammonia, sugars 135, 422 action on aldehy do-glucose pentaace- in phenylosazone formation, 456 tate, 408 ketosylamines to aldoses, 423 ammonolysis, 391, 467 mechanism, 423 as solvent, 370 "reverse", 423 glycosylamine formation, 407 Amice tin, 425 hexosamine formation, 469-471 û>-(p-Aminoacetophenone) ethers of cel- hydrolysis of nucleic acids, 425 lulose, 369 Ammonium, Amino acids, chloride, catalytic action, 408, 412 acylation of aminodeoxy sugars, 448 hydrogen sulfide, reductive denitra- iV-aldonyl derivatives, 450 tion, 170 combinations with carbohydrates, 446- molybdate, effect on rotations, 259 450 amphi compounds, Rosanoff definition, configuration, correlations with L-glyc- 26 erose, 28 Amygdalin, 492, 550 nomenclature, 28 sugar moiety, 492 Aminodeoxyalditols, see Alditols synthesis, 550 Aminodeoxyhexoses, see also Amino- Amygdalose, see Gentiobiose deoxy sugars and individual Amygdalus communis (/3-glucosidase), compounds, 588 quantitative and qualitative test, 650 Amylases, 678 Aminodeoxy sugars, see also Glycosyl- a-amylases, 678 amines and individual sugars ß-amylases, 678 3, 407, 465 action on glycogen, 715 2-amino-2-deoxy, 465 crystalline, 679 3-amino-3-deoxy, 465 liquefying, 678 o-amino-co-deoxy, 470 saccharogenic, 678 iV-acetylation, 471 selective inactivation, 679 oxazoline formation, 474 Amylo-(l —* 6)-glucosidase, 683 analysis, 474 "Amyloid", 637 anhydro derivatives, 378 Amylomaltase, polysaccharide synthesis, biosynthesis, 471 704 856 SUBJECT INDEX

Amylopectin, 94, 675 reductive, 393 isolation, 675 solvolysis, general, 391 nutritional aspects, 805 stability, 378 parenteral feeding, 805 Anhydro sugars, acetal type (glycosans), structure, 675 see also Anhydro sugars, ether synthesis of amylopectin-type poly- type, 188, 220-225 saccharide, 705 acetolysis, 223 Amylopsin, 678 1,6-anhydrohexof uranoses, Amylose, 675 resistance to periodate oxidation, 217 acetate, 678 diketose dianhydrides, 224 film-forming properties, 678 preparation, 221 action of phosphorylase, 682 alkali on aryl glycosides, 221 behavior in cuprammonium solution, mineral acid on sugars, 222 676 reactions, 223 conformation of D-glucose units, 676 structure determination, 222 cyclohexaamylose, 682 synthesis of oligosaccharides, 484 iodine reaction, 676 sucrose, 485 isolation, 675 Anhydro sugars, ether type, 188, 375-399 structure, 675 "Non-reducing" anhydro sugars (gly- synthesis of amylose-type polys ac- cosans) are listed as Anhydro charides, 704 sugars, acetal type Amylosucrase, polysaccharide synthesis, aminodeoxy sugars, 468, 470 705 5,6-anhy drohexoses, 1-Amyl-l-phenylhydrazine, 90 reactions with amino acids, 448 Angelica lactones, 58 2,5-anhydro sugars, osazone forma- Anhydroalditols, see also Anhydro de- tion, 395 rivatives (general), methyl 3,6-anhydroaldohexopyrano- esters, partial, 397 sides, 389 industrial applications, 397 py ranose-f uranose transformations, glycol cleavage, 396 388 inversions during formation, 386 reactivity, effect of anhydro ring, 388 oxidation, 395 synthesis of oligosaccharides, 483, 485 nitrates, 397 Anilides, see also iV-phenylglycosyl- substitution products, 396 amines, 415 synthesis, 382, 384 Aniline, reactions with Anhydro compounds (general), acids, lactones, salts, 415 benzimidazoles, 387, 414 sugars, 412 formation, Anomeric substitution, see also Koenigs - mechanism, 376 Knorr reaction, 194 steric requirements, 376 Anomers, 31 intramolecular rearrangements, 378 anomerization, phenylosazones, 387, 461 acetates, 151 preparation, 376 factors controlling, 156 ring size, 375 configuration, by infrared spectra, 41 ring scission, 390 nomenclature, 42 acetolysis, 394 structural significance, 42 ammonolysis, 391, 467 of acyclic derivatives, 43 direction of opening, 393-4 Anthocyanidin glycosides, 538 hydrolysis, 390 Anthocyanins, 538 inversions, 390 leucoanthocyanins, 539 methoxide ion, 390 Anthoxanthins, 538 SUBJECT INDEX 857

Anthrone, 617 3-O-a-D-glucopyranosyl, 526 Antigens, synthesis (enzymic) 526 blood group, 721 hydrazones, 80 Forssman, 729 methyl 2,5-anhydro-L-arabinofurano- synthetic, 450 side, 389 specificity related to carbohydrate, hydrolysis, 389 451 occurrence, 79 Wasserman, 729 preparation, 83 Antioxidants, 163 5 (or 4)-0-j8-D-xylopyranosyl, 512 Aorta polysaccharide, 712 O-arabino-3,4,5,6-Tetraacet oxy-1,1 -bis- Aphid, 532 (ethanesulfonyl) -1 -hexene, 361 Aphio spiralcola, 532 Arabitol, see Arabinitol Apiin, 553 Arabonic acid, see Arabinonic acid Apiose, 78, 553 Arbutin, 547 structure, 79 methyl, 547 Apples, 95 Aretostaphylos uva-ursi, 547 Apricot (0-glucosidase), 588 Argentic ion, 347 Apurinic acid, 444 Arlitan, see D-Glucitol, 1,4-anhydro Arabans, in pectic substances, 671 Arsenate, effect on enzymic transglu- Arabic acid, 685 cosidation, 530, 682 D-Arabinitol, 243 C-Aryl compounds, preparation, 117 umbilicin, 243 Ascophyllum nodosum, 99 DL-Arabinitol, 244 L-Ascorbic acid (Vitamin C), 331 L-Arabinitol, 244 biosynthesis, 763 D-ara&ino-Hexosone (D-glucosone), 395 precursors, 764 2,3,4,6-tetra-O-acetyl, 334 equilibrium with dehydro-ascorbic behavior toward glycol cleaving acid, 332 agents, 334 histochemical detection, 637 1,2:2, 3:5,6-tri-0-isopropylidene, 334 methylation, 332 5,6-di-O-methyl, 334 occurrence, 331 1-phenyl, 335 mono-O-palmitate, 163 D-Arabinonic acid, stability, 332 3-(j8-D-galactopyranosyl), 356 synthesis, 333 3-(0-D-glucopyranosyl), 356 D-Ascorbic acid, synthesis, 115 1,4-lactone, Ascorbic acids, (general), 328-31 2,3,5-tri-O-methyl, 505 acidity, 331 D-Arabinose, 19, 83 nomenclature, 329 4-O-formyl-2-O-methansulfonyl, 351 preparation, 330 dimethyl acetal, 227 reducing action, 331 methyl tri - 0 - acetyl - ß - D -arabinopy- structure, 329 ranoside, 157 Ash, 500 nutritional aspects, 795 manna, 515, 519 occurrence, 83 Asparogosan, 683 preparation, 83 Aspergillus species, 250 synthesis, 118 A. foetidus, enzyme system, 667 L-Arabinose, 79 A. nicert 365 2,5-anhydro, 395 "NRRL 337", 533 osazone formation, 395 crude enzymes, action on cellulose, 3-O-jS-L-arabinopyranosyl, 510 664 l,2:3,4-dicarbonate, 159 ß-glucosidase, 588 3-O-a-D-galactopyranosyl, 510 inulases, 683 858 SUBJECT INDEX

mycodextran, 706 isolation as copper salts, 610 polysaccharides, 688 labeled, degradation, 624 A. oryzae, virus inhibition, 414 ß-glucosidase, 588 Benzoates, see also individual sugars, transfructosidase, 707 148 inulobiose, 534 acyl migration, 149 Asphodelan, 683 partially esterified, 149 Astragalus family, gum tragacanth, 685 borates as intermediates, 149, 171 Avocado, 253 selective esterification, 149 Azaquinine, enzymic synthesis, 426 Benzohalogeno sugars, see O-Benzoyl- Azotobacter vinelandii, 445 glycosyl halides; also Benzoates and individual sugars B Benzoin condensation, 115 Bacillus species, levan-sucrase, 706 O-Benzoylglycosyl halides, 150 B. macerans, 705 Benzyl ethers, hydrogenolysis, 368 cyclic dextrine, 705 Benzylidene derivatives, 233 B. megatherium, 620-1 alkali labile, 390 B. mesentericus, 681 formation, rules, 231 B. friedländeri, 620-1 hydrogenolysis, 234 Bagasse, 502 Dibenzyl phosphorodichloridate, syn- Barbaloin, 83 thesis of phosphates, 174, 436 Barfoed method (reducing sugars), 616 Bertrand method (reducing sugars), 615 Barium hydroxide, isolation of sucrose, Bertrand Rule, 133 504 Best's carmine stain, glycogen, histo- "Barium saccharate,,, 504 chemical, 638 Barry reaction, 701 Beta vulgaris, 274 Basophilia, 629 manufacture of sucrose, 504 extinction point, 630 Betitol, 276 Bassorin, 686 Bioinosose, see mi/o-Inosose-2 Bearberry leaves, 547 Birefrigence, streaming, polysaccha- Beef lung, 88 rides, 643 galactan, 716 Black mustard, 554 Beet pulp, 83 Blackstrap, 503 Behenic acid, 560 Blocking groups, see also Benzyl, "Bemberg", 663 Benzylidene, Borates, Tri- Benedict method (reducing sugars), 614 chloroacetyl, Ethylidene, Iso- Benzaldehyde, see also Benzylidene and propylidene, Méthylène, Tri- individual compounds, 233 phenylmethyl, and individual Benzenediazonium chloride, compounds, 158 formazans, 455, 460 Blood-group polysaccharides, 721 Benzidine, Tauber's test, 607 from salivas, 728 Benzilic acid rearrangements, 68 occurrence, 721 Benzimidazole, structure, 721 l-D-ribofuranosyl-5,6-dimethyl, 425 Blood sugar, see D-Glucose 2-styryl, 624 Blueberries, 138, 149 Benzimidazole rule, 307 Borate complexes, see Borates Benzimidazoles, 609 Borates, 171, 262 anhydro derivatives, 387, 414 as blocking groups, 149, 171 from acids (aldonic, aldaric, sac- electrophoresis, 604 charinic, etc.), 414 ion-exchange chromâtography, 171, from sugars, 413 603 SUBJECT INDEX 859

ionization, 171 structure, 687 ionophoresis, 604 use, 686 of alditols, effect on rotation, 171 Carbamates, polysaccharides, 695 Borax, effect on rotation, 259 Carbanilates, 160 Boric acid, see also Borates, 262 polysaccharides, estimation of second- aminodeoxysugars, separation, 475 ary hydroxyl groups, 648 titration in presence of mannitol, 263 Carbazole, estimation of Bornesitol, 274 sugars, 617 Bostrychia scorpoides, 248 uronicacids in polysaccharides, 648 Brachiose, see Isomaltose Carbodiimide reagent, 176 Brain sugar, see D-Galactose Carbohydrases, 562 Branched chain sugars, 78 commercial value, 562 Branching enzyme, polysaccharide syn- effect of pH, 570 thesis, 705 history, 562 Brassica nigra Koch, 554 Carbohydrates, 2 BrigPs anhydride (1,2-Anhydro-tri-O- biochemistry, 766-779 acetyl-a-D-glucopyranose), see biosynthesis, 757-766 D-Glucose derivatives color reactions, 607-8 British gums, 677 dental aspects, 807-14 Bromine, "Artificial Mouth" studies, 811 action on starch, 699 decay, oxidation, incidence, 809 "electrolytic" method, 339 types of attack, 812 ketoses, 291, 339 experimental animal studies, 810 polyols, 339 oral clearance factor, 812 rates, 341-2 oral microflora, 814 •y-Bromocrotonaldehyde, 105 post-eruptive effects, 808-11 iV-Bromosuccinimide, hydroxylation of pre-eruptive effects, 808 double bond, 245 saliva, 814 Browning reaction, see Melanoidin re- histochemistry, 624-40 action isotope procedures, 622-4 Brown rots, 665 metabolism, Bupleurum jalactum, 246 glycolysis, 766-75 Burdock, 96 interconversion of sugars, 775-7 Butadiene, 164 pathways, 766 •pyruvic acid oxidation, 777 C nutritional aspects, 779-814 absorption, 781 Calcium, appetite, 800 hydroxide, isolation of sucrose, 504 blood glucose and the urge to eat, saccharate, tri, 504 801 utilization, effect of lactose, 794 caloric value, 780 Calf liver, /3-glucuronidase, 596 candy and "soft drinks", 803 Calf spleen, /3-glucuronidase, 596 digestion, 781 Caffeic acid, 278 parenteral feeding, 805 Cane sugar, see Sucrose protein-sparing action, 803 Cannizzaro reaction, 2-amino-2-deoxy- sources, 779 D-glucose, 476 utilizability, estimation, 795 Canna species, synthesis of sucrose, 524 weight control, 801-804 Carageenan, 685 oxidation products, 299 separation of polysaccharides, 687 oxidizable groups, 299 860 SUBJECT INDEX

photosynthesis, 733-57 acetolysis, 490 qualitative analysis, 602-10 enzymic, 490 quantitative estimation, 610-22 structure, 491, 500 synthesis, cell-free system, 755 Cellotriose, -tetraose, -pentaose, etc., Carbomycin, 466 491 Carbonates, 158 Celluloid, 692 furanoside formation, 203 Cellulose, 662-5 hydrolysis, 159 acetate, commercial preparation, 692 Carbon chain lengthening, see also azo dyes, 369 Cyanohydrin, Diazomethane, biological utilization, 663 Friedel-Crafts, Grignard, Nitro- cuprammonium rayon (Bemberg), 663 me thane, 106 degree of polymerization, 662 glycosylamines, 469 effect of acids, enzymes, 664 Carbon chain shortening, see also Löwen- esterification, 692 feld, MacDonald-Fischer, Ruff, ethers, 695 Weerman, Weygand, Wohl deg- co-(p-aminoacetophenone), 369 radations, Glycals, Hydrogen carboxymethyl, 695 peroxide, Lead tetraacetate, cyanoethyl, 695 Oxygen, Periodate, and indi- ethyl, 695 vidual sugars, 118 hydroxyethyl, 696 Carbon dioxide fixation, see also Photo- methyl, 695 synthesis, 733 solubility, 369 appearance of carbohydrates, 750 mercerization, 663 chemosynthetic (chemautotrophic), nitrate, 168 743 nutritional aspects, 797 Carbon disulfide, 159 dietary fiber, 798 xanthates, polysaccharides, 694 in ruminants, 798 Carbonyl chloride, 159 saccharification of wood, 799 1-Carboxy-D-arabinose, see D-Gluconic oxidation, acid, 2-keto analysis of groups formed, 697 Carboxy dismutase, 755 periodate-oxidized, structure, 701 2-Carboxypyrrole, 731 "tendering", 697 Cardiac glycosides, 543 physical characteristics, 662 Carob bean, 250 soda cellulose, 694 galactomannans, 684 swelling, 663 Carotene, 740 synthesis, enzymic, 707 occurrence, 741 Celtrobiose, see D-Altrose, 4-0-/3-D- Cartilage, 469 glucosyl chondromucoid, 723 Cephalin, 272 Cataracts, 792 Cerebrosides, 88, 560 Cataractogenesis, fatty acid components, 560 D-galactose, 89, 792 structure, 560 D-xylose, 85, 796 Cerebrose, see D -Galactose Cathartic-acting glycosides, 83 Ceric sulfate, 361-2 Cellobiose, 490 Chaemerops humilis, 275 homologs, 491 Chaetonium globosum, 664 metabolism, 491 Chei-Hou, 246 nutritional aspects, 795 Chicory, 96 octaacetate, 490 Chinese rhubarb, 161 preparation from cellulose, Chinovin, 100 SUBJECT INDEX 861

Chinoyose, see D-Glucose, 6-deoxy Chromatography, 603 Chitaric acid, see D-Glucaric acid, 2,5- adsorbents, 603 anhydro adsorption, 607 Chitin, 465, 715 ion-exchange, 603 occurrence, 715 separation of borates, 171, 603 isolation, 715 paper, 604 structure, 715 acidic substances, detection, 631, Chitobiose octaacetate, 715 635 Chitonic acid, see D-Mannonic acid, as guide for cellulose column, 607 2,5-anhydro carbohydrates, solvent systems, 605 Chitosamine, see D-Glucose, 2-amino-2- sugar phosphates, solvent systems, deoxy 605 Chitosaminic acid, see D-Gluconic acid, procedures, 604 2-amino-2-deoxy Rf, 605 Chitose, see D-Mannose, 2,5-anhydro Rx, 606 Chalamydomonas eugametos, 541 spray reagents, 606 Chloric acid, preparation of 2-keto- Chromic acid, 361-2 aldonic acids, 345 induction of metachromasia (histo- Chlorine, chemical), 632 as oxidant, 342 Cladinose, 78 oxidation of glycoseens, 335 Clerget method (reducing sugars), 612 Chloroacetic acid, preparation of car- Cinchona, 100, 278 boxymethylcellulose, 695 Cionia intestinalis, 278 Chlorogenic acid, 278 Citric acid cycle, 777 Chlorous acid, 345 Cobalt sulfide (catalyst), 248 polysaccharides, aldehyde and ketone Cocarboxylase (TPP), 747 groups, 649 Cocositol, see scyllo-Inositol Chloroplasts, 735 Cocos palm, 274 composition, 736 Coenzyme, structure, 735 A, 748 Chlorophyll, 741 acetyl, 750 a, 740 structure, 748 occurrence, 741 1,437 structure, 740 II, 438 b, 740 III, 438 occurrence, 741 Coenzymes, 437, 745 structure, 740 flavin, 439 localization in plants, 735 uridine type, 440 Chlorosulfonic acid, 170 Coffee emulsin, glycosidase system, 590 Cholla gum, 512 Collagen, 722 Chondroitin, 720 Color reactions, 607-8 sulfate, 321, 719 Compositae, 96 isolation, 719 fructans, 683 occurrence, 719 Condurango tree, 277 structure ,-719 Conduritol, 277 Chondromucoid, 723 configuration, 283 Chondrosamine, see D-Galactose, 2- Configuration, amino-2-deoxy absolute, 15 Chondrosine, 321, 719 and optical activity, 9 Chondrus crispus, 685 anomeric center, 35 862 SUBJECT INDEX

determination, conductivity in boric Cupric sulfate, phenylosotriazoles, 460 acid, 262 Cyanohydrin synthesis, for lengthening methods for modifying, see also Epi- carbon chain, 106 merization, 125 2-amino-2-deoxy sugars, 469 relative, Fischer convention, 15 Cl labeling, 135 Conformations, pyranose rings, 40 polysaccharides, determination of al- O-acylglycosyl halides, 152 dehyde and ketone groups, 650 axial-equatorial substituents, 210 proportions of epimers, 107 conformational stability, 210 quantitative determination of aldoses, D-glucose units in amylose, 676 618 glycosides, 210 separation of epimers, 107 Coniferin, 548 use in Rosanoff system of nomencla- relation to lignin, 548 ture, 22 Coniferyl alcohol, 549 steric effects, 106 dehydrogenation, 549 Cycas revoluta, ß-glucosidase, 588 Convoivulaceae, 99 Cyclitols, see Inositols, Polyols (cyclic), Convoivulin, 99 and individual compounds Copper number, cellulose, 649 Cyclohexanehexols, see Inositols Cordycepose, 78 Cyclohexanepentols, see Inositols, mono- Cori ester, 182 deoxy, and individual com- Cornea, pounds keratosulfate, 722 Cyclohexanetetrols, see Inositols, di- polysaccharide, 712 deoxy Corn cobs, 85 Cyclohexenetetrols, 277 Corn sirup unmixed, 93 Cymarin, 544 Corn starch, 91 Cymarose, 544 Corn sugar, see D-Glucose Cysteine, reactions with sugars, 447 Cottonseed hulls, 85 Cytidine, 425 Cottonseed meal, raffinose, 518 di- and triphosphoric acids, 437 o-Coumaric acid, 549 Cytosine, 425 Coumarin, 549 o-Coumarinic acid, 549 D C.S.U., see Corn sirup, unmixed Crab shells, 468 Dahlias, 96 Crocetin, 541 f rue tans, 683 sexual influence, Chlamydomonas, 541 Dambonitol, see rai/o-Inositol, 1,3-di-O- Crocin, 541 methyl sugar moiety, 492 Dambose, see raî/o-Inositol Crocus sativus, 541 Dandelions, 96 pollen, 539 Daviesia latifolia, 149 Crown-gall polysaccharide, 690 Dead Sea Apple, solanum alkaloids, 546 Cryptococcus neoformans, 632 Decarboxylation, see also Ruff degrada- Cucurbita moschata, 0-glucosidase, 588 tion, Cuprammonium solution, polysaccharides, estimation of uronic glycol cleavage, 218 acids, 648 optical rotation, polysaccharides, 655 Decitols, 257 rayon, 663 Degradation, see Carbon chain shorten- Cupric ion, ing as oxidant, 365, 613 Dehydrogenation (catalytic), effect of pH, 364 platinum and oxygen, 356, 613 in ammoniacal solution, 364 sodium ferropyrophosphate, 357 SUBJECT INDEX 863

Demissidin, see Dihydrosolagenin Dextrans, see D-Glucans Dendroketose, 65 Dextrins, 677 Dental decay, incidence, 809 cyclic, 681 D-enzyme, 705 synthesis (enzymic), 705 Deoxyalditols, see also individual com- limit, 680 pounds. Note: ω-deoxy com- nutritional aspects, 783 pounds listed under parent; all Schardinger, see cyclic others under Deoxy and appro- torréfaction, 677 priate configurational prefix, 226 Dextrose, see D-Glucose. 2-Deoxy-D-arafo*no-hexitol, 266 Diabetes mellitus, fructose utilization, 1,5-anhydro, 382, 400 787 pyridine complex, 266 Dialdoses, preparation, 335 2-Deoxy-D-er?/i/iro-pentose, 87 Diaminobenzene, see Phenylenediamine biosynthesis, 88, 762 Diastases, see Amylases hydrazones, 80 Diazomethane, see also Diazomethane nucleosides, 424 synthesis occurrence, 87 methylation, 371 preparation, 87 reactions with acyl halides, 111 aldol condensation, 114 synthesis of methyl aldonates, 162 Grignard reaction, 116 xanthates, replacement with methyl Schiff's reaction, 635 groups, 694 synthesis, 68 Diazomethane synthesis, for lengthen- Deoxyhalogeno derivatives (Halogeno ing carbon chain, 111 esters), see also O-Acylglycosyl preparation of, halides, Glycosyl halides, 172, 0-a.cetyl-keto sugars, 144 376 D-aZiro-heptulose, 112 2-Deoxy-D-Z2/£o-hexaric acid, 313 2-deoxy aldonic lactones, 113 1-Deoxyketoses, preparation, 113 1-deoxy ketoses, 113 Deoxypentosenucleic acids (DNA), 87, 1-deoxy-l-halogenoketoses, 172 444 D- and L-fructose, 112 Feulgen reaction, 635 D- and L-graZacfo-heptulose, 112 hydrolysis, 425, 430 ketoses, 111 acid, 444 L-manno-heptulose, 112 alkali, 444 D- and L-sorbose, 112 macrostructure, 444 Wolff rearrangement, 113 structure, 434 Diazouracil test, 502, 525, 608 synthesis, 445 Dicyclohexyl carbodiimide, synthesis of ' 'Transforming principle", 445 ADP and ATP, 436 Deoxyribonuclease, 637 Digallic acid, 160 Deoxyribonucleic acids, see Deoxy- Digitalis species, 543 pentosenucleic acids D. lanata, 544 2-Deoxy-D-ribose, see 2-Deoxy-Ό-erythro- Digitoxose, 544 pentose Diglycosylamines, see Glycosylamines Deoxy-sq/Mo-inositol, see rm/o-Inositol, Diheterolevulosan (=Difructose dian- 2-deoxy hydride), see D-Fructose deriv- Deoxy sugars, see also individual sugars atives and "Note" under Deoxyaldi- Dihydroconduritol, 283 tols Dihydro-D-glucal, see 2-Deoxy-D-ara- non-terminal, synthesis, 131 fono-hexitol, 1,5-anhy dro terminal, synthesis, 130 Dihydrosolagenin, 547 Detoxication, 599 Dihydroxy acetone, 864 SUBJECT INDEX

acceptors, 771 Emulsifiers, donors, 771 food, algin, 687 1-phosphate, aldolase catalyzed con- paper (sizes), 696 densations, 758 Emulsin, see also Enzymes and individ- Diketoinositols, 290 ual emulsins, 563 Diketose dianhydrides, 224 structure of glycosides, oligosaccha- p-Dimethylaminobenz aldehyde, Ehrlich rides, 600 test, 474, 730 Enantiomorphs, 10 Dimethyl sulfate, 369 behavior toward symmetrical and glycoside formation, 202 asymmetrical reagents, 11 Dinitrogen pentoxide, nitrating agent, effect of enzymes, 581 693 resolution, 11, 90, 599 o-Dinitrobenzene, reducing sugar test, End-for-end inversion, 128 608 End-group assay, 650 2,5-Dinitrosalicylic acid, Enzymes, 562, 733 polysaccharides, aldehyde and ketone activity, measurement, 571 groups, 649 standard substrates, 572 Diphenylformazans, see Phenylhydra- aldolase, general reaction, 758 zones amylases, 678 Diphosphopyridine nucleotide (DPN), Aspergillus foetidus system, 667 745 Aspergillus niger, Dithiocarbonates, 159 cellulase, 665 polysaccharides, 694 cellobiase, 665 Dithioacetals, see Thioacetals branching enzyme, 705 Dithioglycol, 226 carboxydismutase, 755 6,8-Dithiooctanoic acid (a-lipoic acid), cellulase, 663 747 dehydrogenases, TPN-specific, 769 Disulfones, see MacDonald-Fischer deg- deoxyribonuclease, 637 radation dextransucrase, 502 D, L nomenclature, 21 dipeptidase, 449 Disaccharides, see also Oligosaccharides dissociation constant, 565-6 and individual sugars, 351 effect on activity, Dodecitol, 258 configuration, 581 Dogwood, 274 pH, 570 D.P. (= degree of polymerization), see ring size, 581 Oligosaccharides, Polysaccha- temperature, 572 rides emulsins, 563 Drying oils, synthetic, 398 enzyme efficiency, 572 Dulcitol, see Galactitol variation with changes in aglycon, Dyes, water soluble, 369 585-6 Dyera tree, 274 0-fructofuranosidase, 591 fungal, polygalacturonase, 671 E a-galactosidase, 501 Eberthella species, 620-1 0-galactosidase, 496 Ehrlich reagent, 474 galactosyl transferase, 498 sialic acid, 729 galactowaldenase, 497, 775 Elasmobranch fish, 274 ß-glucosaminidase, 473 Electrophoresis, borates, 604 glucose oxidase, 366, 619 Elson and Morgan procedure (amino glycosidases, mechanism, 566 groups), 650 hexokinase, sucrose synthesis, 522 absorption maximum, 730 hexose diphosphatase, 755 SUBJECT INDEX 865 hexosidases, effect on pentosides, 577, sucrose phosphorylase as transglyco- 580 sidase, 528 hyaluronidases, 718 role of arsenate, 530 histochemical use, 639 Takadiastase,as transfructosidase, 532 inhibition, 570 transaldolase, 755, 771 inulases, 683 transfructosidase, 530-2 invertase, preparation, 591 transglycosidases, 568 kinetic equations, 563 transketolase, 755, 770, 772 laminaranase, 688 uridyl transferase, 497 levansucrase, as transfructosidase, 530 use in histochemical identification of maltase, preparation, 594 carbohydrates, 638 malt diastase, histochemical use, 639 "Wertigkeit", 572 mammary tissue, 497 xylose isomerase, 761 mechanism of action, 563 xylulose kinase, 761 melibiase, 501 Z-enzyme, 680 Michaelis constant, 565 Epichitosamine, see D-Mannose, 2- mutarotation catalysis, 50 amino-2-deoxy my rosin, 555 Epiglucosamine, see D-Mannose, 2- Neurospora crassa system, 471 amino-2-deoxy, and D-Altrose, pectases, 671 2-amino-2-deoxy pectinases, 671 Epiisosaccharic acid, see D-Glucaric histochemical use, 640 acid, 2,5-anhydro P-enzyme, 682 Epilactose, see D-Mannose, 4-0-/3-D- phosphodiesterase, 442 galactopyranosyl phosphoglucomutase, 497, 776 Epimelibiitol, 492 synthesis of sucrose, 522 synthesis of planteobiose, 501 phosphoketopentoisomerase, 761 Epimelibiose, 491 phosphopentoisomerase, 755 occurrence, 492 phosphopentokinase, 755 preparation, 492 phosphoriboisomerase, 761 structure, 492 phosphorylase, Epimerization, see also Glycals, syn- Pseudomonas saccharophila, 506 thesis; Waiden inversion, 125 synthesis of aldonic acids, disaccharides, 524-8 alkali catalyzed, 125 polynucleotides, 445 tertiary amines, 126 sucrose, 521 sugars, see also Lobry de Bruyn- polygalacturonâse, 671 Alberda van Ekenstein trans- Polysaccharides, nature of glyco- formation, 125 sidic linkage, 654 Epimers, 10 Primula officinalis and P. vulgaris D-Epirhamnose, see D-Glucose, 6-deoxy systems, 551 Epoxides, see also Anhydro derivatives Proteus vulgaris system, 516 and individual compounds, 165, R-enzyme, 683 376 reaction constant, effect of enzyme formation, 165, 376-82 concentration, 572 preparation of deoxy sugars, 132 ribonuclease, 637 scission, 166, 390 pancreatic, 443 ammonolysis, 391 specificity, direction, 394 aglycon, 582 hydrogenolysis, 393 sugar moiety, 581 hydrolysis, 390 spleen, 444 Eremostachys labiosa} 520 866 SUBJECT INDEX

Ergot, 0-glucosidase, 588 aldonates, 162 Ericaceae, 547 borates, 171 Eriodictyol, 540 carbanilates, 160, 648 L-rhamnoside, 540 carbonates, 158, 203 Ervum lens, 519 cyclic, 139 Erythraric acid, see also Tetraric acids, diphenates, 401 di-O-methyl, 427 ethoxy formates, 158 1,4-Erythritan, see Erythritol, 1,4-an- formation, see Esterification and in- hydro dividual sugars Erythritol, 243 hydrolysis, 139 1,4-anhydro, 384 methanesulfonates, 163 Ό-er y thro-L-galacto-Octitol, 256 methoxyformates, 158 D-erythro-2,3-Hexosone, naturally occurring, 138 1,5-anhydro, 395 nitrates, 168 erythro-manno-Octitol, 257 preparation of anhydro derivatives, O-erythro-L-manno-Octose, 110 376 Erythromycin, 465 partial, 158 L-Erythronic acid, 2-keto, total syn- phosphates, 138, 172 thesis, 326 preparation in sulfuric acid, 163 D-erythro-Pentulose (ü-ribulose), 86 propionates, 602 hydrazones, 80 distillation, 602 labeled, degradation, 624 sulfates, 170 occurrence, 86 sulfonates, 163, 376 5-phosphate, 183 preparation of anhydro derivatives, Hexose Monophosphate Shunt 376 scheme, 769 surface active, 138, 163 photochemical production, 753 p-toluenesulfonates, 163 diphosphate, photochemical produc- preparation of, tion, 753 anhydro derivatives, 376 preparation, 86 unsaturated compounds, 164 L-ert/iÄro-Pentulose, replacement, 397 D-glucosyl L-er^/iro-pentuloside, 524 xant hates, 159 synthesis, 526 Ethanedithiol, 226 D-Erythrose, 25 Ethanol, production by glycolysis, 767 4-phosphate, 184 Ethanolamine, 476 metabolism, 771 Ethanethiolysis, 201 DL-Erythrose, synthesis, 105 Etherification, see O-Alkylation, 0- D-erythro-i>-talo-Octitol, 257 Methylation, and individual Escherichia coli, 250, 445, 620-1 compounds amylomaltase, 704 Ethers, 367-99 ß-glucuronidase, 596 allyl, 369 Escherichia freundi, 250 benzyl, hydrogenolysis, 368 Esparto grass, xylan, 668 cyclic, see Anhydro derivatives, Epox- Esterification, 139 ides, and individual compounds catalysts, 139 hydrolysis, 368 hydroxyl groups, order of reactivity, industrial importance, 368 139 occurrence, 367 influence of ring structure, 139 preparation, 367 polysaccharides, 691 triphenylmethyl, 368 Esters, 138-9 Ethoxyformates, 158 acyclic, 139 Ethyl chloroformate, 158 SUBJECT INDEX 867

Ethylidene derivatives, 235 Folin-Malmros method (reducing sug- formation, rules, 231 ars), 616 synthesis from acetylene, 235 Folin-Wu method (reducing sugars), 615 Eulota peliomphala, 590 Formal derivatives, see Méthylène de- Euonymus atropurpureus, 252 rivatives Euphorbia pilulifera L., 271 Formaldehyde, European palm, 275 acetals, see Méthylène derivatives and Explosives, individual compounds cellulose trinitrate (gun cotton), 693 polymerization, 103 starch trinitrate, 693 quantitative estimation, 350 Formamide, F gelatinization of polysaccharides, 692 Formates, Fehling test (reducing sugars), 608 formation during glycol cleavage, 350 glycofuranosiduronic 3,6-lactones, 325 Formic acid, -Soxhlet, quantitative method, 613 action on anhydroalditols, 396 Fermentation, 766, see also Emulsins, quantitative estimation, 350 Enzymes, Yeast Formose, 103 quantitative determination of sugars, Formulas, 619 Fischer-Tollens, 9, 37 microorganisms and substrates, Haworth, 38 620-1 Sachse (Reeves), 40 role of phosphates, 173 Forsythia pollen, lactose, 495 Ferricyanide, see also Hagedorn-Jensen Forsythia suspensa, 554 method, Fraxinus ornus, 249, 515, 519 polysaccharides, determination of al- Fraxinus rotundifolia, 249, 515 dehyde and ketone groups, 649 Friedel-Crafts reaction, 116 reducing sugars, 616 C-aryl compounds, 117 Feulgen reaction, 635 Frog spawn, 88 Films, Fructans, 683 amylose acetate, 678 /8-Fructofuranosidase, 562 cellulose acetate, 692 activity in newborn mammals, 785 polysaccharides, 643 Fischer convention, projection formulas, chemical composition, 575 commercial utilization, 591 9 preparation, 591 Fischer synthesis, glycosides, 191 transfructosylation, 707 conditions affecting isomerism, 191 yeast (invertase), Fistulina hepatica, 244 kinetics of hydrolysis, 592 Flavanol glycosides, 538 specificity, 592 sexual influences, Chlamydomonas, 511 D -Fruc t of uranoside, Flavanols, quercitin, 539 a-D-glucopyranosyl, see Sucrose Flavanones, 538 hesperitin, 540 oligosaccharides, 513, 517-19, 531-2 Flavinadenine dinucleotide (FAD), 440, /8-Ä-Fructosidase, see 0-Fructofurano- 746-7 sidase Flavin mononucleotide, see Riboflavin D-Fructose, 95 5-phosphate assimilation, 97 Flavones, 538 blood level, 786 Flaxseed mucilage, 90 1,6-labeled, 136 Florideae species, 554 degradation, 624 Floridoside, 554 labeled, uniformly, 135 868 SUBJECT INDEX

metabolism, 786 D- or L-Fucose, see D- or L-Galactose, insulin independence, 787 6-deoxy, nutritional aspects, 786 Fucus, 99 occurrence, 95 2-Furaldehyde, see also 2-Furylidene preparation, 96 derivatives, 57 structure, 7 determination, 619 synthesis, formation, mechanism, 58-9 from three-carbon fragments, 114 5-halogenomethyl, 58 total, 103 5-hydroxymethyl, 57 utilization, 97, 786 Furanose, see also individual sugars, 33 by spermatozoa, 786 Furanosides, see also Glycosides and in diabetes mellitus, 787 individual sugars, 33 in parenchymal hepatic disease, 787 from carbonates, 203 D-Fructose derivatives, Furfural, see 2-Furaldehyde 1,3,4,6-tetra-O-acetyl, 156 Furocoumarin, 550 tetra-O-acetyl-l-deoxy-l-diazo-fcefo, Furocoumarinic acid, 549 145 2-Furoic acid, 5-hydroxymethyl, 468 penta-O-acetyl-fceio, 145 2-Furylidene derivatives, 235 3-O-alkyl, alkaline hydrolysis, 509 G iV-alkyl-D-fructosylamines, conversion to aldose derivatives, 423 Galactans, 716 1-amino-l-deoxy, 461 agar, 685 1,3,4,5-tetra-O-benzoyl, 148 carageenan, 686 1,3,4,6-tetra-O-benzoyl, 148 in pectic substances, 671 penta-O-benzoyl-fcefo, 148 synthesis, 707 1-dibenzylamino-l-deoxy, 423 /S-Galactan, see Stachyose calcium fructosate (or levulate), 96 €-Galactan, 510 l,2:4,5-dicarbonate, 159 Galactaric acid, 80, 313 6-deoxy, 524 2-deoxy, see 2-Deoxy-D-Jt/zo-hexaric enzymic synthesis, 759 acid 6-deoxy-D-fructoside, D-glucosyl, 524 Galactinol, see myo-Inositol, l-0-(a-D- 1-deoxy-l-p-toluino, 422 galactosyl) quinoxaline formation, 414 Galactitol, 251 difructose dianhydrides, 224 1,5-anhydro-D-, 378 6-O-a-D-galactopyranosyl, see Plan- l,5:3,6-dianhydro-D-, 378 teobiose 6-deoxy-L-, 134 4-O-jS-D-galactosyl, 481 biochemical oxidation, 134 3-O-a-D-glucopyranosyl, see Turanose nutritional aspects, 797 5-O-a-D-glucopyranosyl, 534 synthesis, 252 hydrazones, 80 total, 106 1,2 and 2,3-O-isopropylidene, 239 D-Galactofuranoside, di-O-isopropylidene, 238-9 ethyl <*, 200 3-O-methyl, 238 ethyl ß, 156, 200 1,3,4,5-tetra-O-methyl, 238 Galactomannans, 684 6-phosphate, 181 D-Galactomethylose, see D-Galactose, Hexose Monophosphate Shunt 6-deoxy scheme, 772 D-Galactopyranoside, 1,6-diphosphate, 181 ethyl a, 20 Fruit sugar, see D-Fructose 2-glycerol, uniformly labeled, 135 L-Fucitol, see Galactitol, 6-Deoxy-L-, methyl 3,4-anhydro-|8, 391 SUBJECT INDEX 869

methyl 3,6-anhydro, 388 1,2:3,4-di-O-isopropylidene-a, 237 conversion to dimethyl acetal, 388 6-O-chloroformyl, 159 Galactosamine, see D-Galactose deriva- 2,3,4,5-tetra-O-methyl, 496 tives, 2-amino-2-deoxy N - phenyl - ß - D - galactosylamine · D-Galactose, 88 carbon tetrachloride, 411 absorption, 789 1-phosphate, 174 biosynthesis, 89 conversion to D-glucose 1-phosphate, cataractogenesis, 89, 792 775 fermentation, 90 DL-Galactose, 90 from D-sorbose, 62 L-Galactose, 90 labeled, uniformly, 135 3,6-anhydro, 4- O-0-D-galactopyrano- nutritional aspects, 789 syl, 511 cataractogenic action, 89, 792 6-deoxy (L-fucose), 98 galactosemia, 794 hydrazones, 81 occurrence, 88-9 occurrence, 98 preparation, 89 preparation, 99 quantitative determination, fermenta- occurrence, 90 tion method, 621 preparation, 90, 713 utilization, effect of dietary fat, 789 Galactosemia, 90, 794 D-Galactose derivatives, a-Galactosidase, 2,3,5,6-tetra-O-acetyl-, 156 coffee emulsin, 590 2,3,4,6-tetra-O-acetyl-a-D-galactosyl melibiase, bottom yeast, 593 trimethyl ammonium bromide, various sources, enzymic action com- 222 pared, 594 penta,-0-a,cety\-aldehydo, 157 ß-Galactosidase, 1,1-dichloro-l-deoxy, 157 alfalfa emulsin, 590 penta-O-acetyl-D-galactoseptanose, aglycon specificity, 591 146 almond emulsin, 577 2-amino-2-deoxy, 380, 465 sweet-almond emulsin, 591 iV-acetyl, 719 aglycon specificity, 591 analysis in presence of 2-amino-2- types, 590 deoxy-D-glucose, 475 D-Galactoside, 3-0-G8-D- glucopyranosyluronic 2-glycerol-a, 554 acid), 321, 719 hydrolysis, enzymic, effect of agly- nutritional aspects, 797 con, 585 occurrence, 466 umbilicin, 243 preparation, 469 Galactowaldenase, 90, 440 synthesis, 467 Galactotransferase, 707 1,6 - anhydro - a - D - galactofuranose, Galactotriose, 520 221-2 Galacturonans, 671 resistance to periodate, 350 methyl ester, 671 pectic acid, 671 1,6-anhydro-/8-D-galactopyranose, 221 D-Galacturonate, methyl tetra-O-ace- l,2:3,4-dicarbonate, 159 ty\-aldehydo, 229 6-deoxy (D-fucose), 99 Gallic acid, 160 6-deoxy-L-mannosyl, 511 Gallotannins, 160 diethyl dithioacetal, 200 Galtose, 63 3-0-0-D-galactopyranosyl, 510 Gangliosides, 88, 560 4-O-a-D-galactopyranosyl, 510 Garlic, scorodose, 520 6-O-D-galactopyranosyl, 511, 534 Gaucher's disease, 560 hydrazones, 80 Gelation, fruit juice, 670 870 SUBJECT INDEX

Gelidium amansii, 511 pyridine complex, 266 agar, 685 synthesis, 248 Gentian, 513 DL-Glucitol, 249 Gentianose, 513 L-Glucitol, 248 Gentiobiose, 492 D-Glucodecitol, 257 octa-O-acetyl, anomerization, 495 D-Glucofuranoside, amygdalin, 550 methyl a, 193 o-chlorophenyl ß-gentiobioside, 599 5,6-carbonate, 203 in "hydrol", 493 methyl ß, 193 occurrence, 492 3,6-anhydro, 168 preparation, 492 "a-Glucoheptulitol", 254 structure, 493 D-grZwco-Heptulose, 62 synthesis, 493 D-Glucomethylose, see D-Glucose, 6- D-Glucal, 400 deoxy tri-O-acetyl, 172, 382 D-Gluconic acid, 340 isomerization, 402 2-amino-2-deoxy, 379, 466 reactions, 399-402 4-0-/3-D-galactopyranosyl, 496 Glucamine, see D-Glucitol, 1-amino-l- 4-O-a-D-glucopyranosyl, 499 deoxy tri-O-isopropylidene, 238 D-Glucans, 688 2-keto, 239 dextrans, 688 occurrence, 326 clinical use, plasma volume ex- 1,4-lactone, 340 pander, 688 tetra-O-methyl, 496, 499 antigenic action, 689 2-O-methyl, 238 fate, 689 2,3,4,5-tetra-O-methyl, 500 preparation, 689 6-phosphate, 86 Leuconostoc mesenteroides, 688 enzymic oxidation, 86, 183 structures, 689 Hexose Monophosphate Shunt synthesis, 706 scheme, 769 laminar an, 688 polyester, 162 mycodextran, 706 utilization, biochemical, 302 D-Glucaric acid, 80, 313 D-Glucononitol, 257 2,5-anhydro, 379 D-Glucopyranoseen, tetra-O-acetyl-1,2, "Glucidamins", 724 382 D-Glucitol (sorbitol), 247 D-Glucopyranoside, 1-amino-l -deoxy, 475 benzyl 2 - carbobenzyloxamino - 2 - 2-amino-2-deoxy, 476 deoxy-a, 466 1,4-anhydro, 385-6 jS-D-fructofuranosyl-a, see Sucrose 3,5-0-benzylidene-6-chloro- 0-D-fructofuranosyl-(2 —> l)-0-D-fruc- tofuranosyl-(2 -* 1), 707 6-deoxy, 390 0-a-D-galactopyranosyl-(l —► 6) -0-/3- 1,5-anhydro, 382-3 D-fructofuranosyl-(2 —> l)-a, 516 2,5 - anhydro -1,6-di-O- benzoyl, 1-O-a-D-glucopyranosyl-a, see Treha- 387 lose l,4:3,6-dianhydro, 164, 385 0-a-D-glucopyranosyl-(l —► 3)-/3-D- l,5:3,6-dianhydro, 378 fructofuranosyl-(2 —> l)-a, 515 1-deoxy-l-thio, 248 methyl, 6-O-a-D-galactopyranosyl, 501 a, 213 1,3:2,4:5,6-tri-O-methylene, 232 3,4,6-tri-O-acetyl, 204 nutritional aspects, 797 tri - 0 - acetyl - 3 - O - p - tolylsul- occurrence, 247 fonyl, 168 SUBJECT INDEX 871

3,6-anhydro-a, 170 6-N-alanino-6-deoxy, 448 3,6-anhydro-/S, 376 2-amino-2-deoxy, 378, 465 4,6-dichloro-4,6-dideoxy-a, iV-acyl derivatives, 448 2,3-disulfate, 172 analysis in presence of 2-amino-2- 4,6-0-(2-furylidene)-a, 236 deoxygalactose, 475 3-keto, 328 fermentation, 473 6-nitrate, alkaline elimination, 170 3 - O - 03 - D - glucopyranosyluronic salicyl 6-0-benzoyl-/3, 149 acid), 319 theobromine tetra-0-acety 1-/3, 206 nutritional aspects, 797 iS-D-Glucopyranosiduronase, see /3-Glu- occurrence, 466 curonidases phenylosazone, 466 D- or L-Glucosamine, see D- or L-Glucose, preparation, 468 2-amino-2-deoxy phosphorylation, 473 Glucosaminic acid, see D-Gluconic acid, structure, 466 2-amino-2-deoxy 6 - amino - 6 - deoxy - 1,2 - O - iso- propylidene, 381 Glucosaminol, see D-Glucitol, 2-amino- 1,2-anhydro, 2-deoxy 3,4,6-tri-O-acetyl, 157, 204, 219, 221 Glucose (industrial) = Corn Sirup Un- 1,6-anhydro, 221 mixed, 93 preparation of cellobiose, 491 D-Glucose, 91 scission by phosphorus pentabro- blood glucose level, 801 mide, 172 effect on urge to eat, 801 6-O-a-L-arabinosyl, 510 configuration, 13 3-O-benzoyl, 158 1-deuterio, 62 6-O-benzoyl, 138, 149 glucose-water system, phase diagram, 3,5,6-tri-O-benzoyl, 158 92 3,4,5,6-tetra-0-benzoyl-aZde%do, 158 3,4-labeled, 135, 622 4,6 - O - benzylidene -1,2 - O - isopro- 6-labeled, 136 pylidene, 234 labeled, uniformly, 135 3,5 - O - benzylidene -1,2 - O - isopro- mutarotation, 50, 53 pylidene, 234 nutritional aspects, 785 5,6-carbonate, 203 occurrence, 91 6-carbonate, bis (1,2,3,4-tetra-O-ace- preparation, 91 tyl), 159 quantitative estimation with D -glu- l,2:5,6-dicarbonate, 159 cose oxidase, 619 6-deoxy, 99 ring formulations, 30 5-0-/3-D-glucosyl, 485 structure, 7 occurrence, 100 synthesis, total, 103 phenylosazone, 81 synthesis of rayo-inositol, 272 preparation, 100 L-Glucose, 78 6-0-(6-deoxy-/3-L-mannosyl), 512 D-Glucose derivatives, 6-deoxy-6-nitro, 273 3,4,6-tri-O-acetyl, 156 diethyl dithioacetal, 143 l,2,3,4-tetra-0-acetyl-/3, 158 penta-O-acetyl, 143 2,3,4,6-tetra-O-acetyl, 156, 158 6-O-D-galactosyl, 534 penta-O-acetyl, 140-1 4-0-/3-D-galactopyranosyl, see Lactose anomerization, 154 6-O-a-D-galactopyranosyl, see Melibi- penta-O-acetyl -aldehydo, 143 ose 1,3,4,6 - tetra - O - acetyl - 2 - O - 0-D-galactosyl-(l -♦ 6)-0-D-galacto- (trichloroacetyl)-a, 157 syl-(l -> 4), 534 872 SUBJECT INDEX

0-D-galactosyl-(l —* 6)-0-D-galacto- 1,2-0-isopropylidene-a;-D-glucof u- syl-(l->6),534 ranose, 237 l-O-galloyl-0, 161 5,6-carbonate, 203 penta-O-galloyl, 160 3,5,6-tri-O-methyl, 238 2-0-/3-D-glucopyranosyl, 511 3,5-orthoborate, 171 3-0-/3-D-glucopyranosyl, 511 1,2:5,6-di-O-isopropylidene-a-D-glu- 4-O-a-D-glucopyranosyl, see Maltose cofuranose, 237 4-0-j3-D-glucopyranosyl, see Cellobiose 3-O-p-tolylsulfonyl, 165 6-O-a-D-glucopyranosyl, see Isomal- 1,2:3,5-di-0-isopropylidene-û!-D-glu- tose copyranose, 238 6-O-jS-D-glucopyranosyl, see Gentiobi- pentamethacrylate, 163 ose 2-O-methyl, 694 D-glucopyranosyl bromide, 3-O-methyl, 238 3,4,6 - tri - 0 - acetyl - 2 - bromo - 2 - 2,3,5,6-tetra-O-methyl, 212,386 deoxy, 172 2,3,4,6-tetra-O-methyl, 62, 212 tetra-O-acyl, 150 transformation in alkaline deute- tri-0-acetyl-6-bromo-6-deoxy, 172 rium oxide, 62 D-glucopyranosyl chloride, mutarotation, 55 3,4,6 - tri - 0 - acetyl - 2 - 0 - (tri- penta-O-methyl aldehydo, 142 chloroacetyl)-/3, 156, 158 3-O-methylsulfonyl, 88 tetra-O-acyl, 150 degradation to 2-deoxy pentose, 88 tetrasulfate, 170 pentanitrate, 169 tetra-O-p-tolylsulfonyl, 164 iV-phenyl-D-glucosylamine, 409 0-a-D-glucopyranosyl-(l —» 4)-0-a-D- 1-phosphate, 174-5, 182 glucopyranosyl-(l —> 4), 513 conversion to D-glucose 6-phosphate, 0-a-D-glucopyranosyl-(l —> 6)-0-a-D- 776 glucopyranosyl-(l —> 4), see 6-phosphate, 182 Panose 3-sulfate, 170 0-a-D-glucopyranosyl-(l —> 6)-0-«-D- l-thio-/3-D-glucopyranose, tetra-O-ace- glucopyranosyl-(l -* 6), 520 tyl, 383 di-D-glucopyranosyl disulfide, octa-O- uridine diphosphate, 775 acetyl, 383 vicine, 425 D -glue opy r anosy luridine -5 '-py r ophos - 6-O-a-D-xylosyl, 483 phoric acid, 775 6-0-/3-D-xylosyl, 483, 512 iV-D-glucosylalanine, 447 L-Glucose derivatives, iV-D-glucosylcytosine, 417 2-deoxy-2-iV-methylamino, 78, 465, 558 D-glucosyl ethyl thiohydantoate, 6-deoxy-3-O-methyl, 78 tetra-O-acetyl, 416 Glucose dehydrogenase, 366, 619 D-glucosyl fluoride, 152 1,2-D-Glucoseen, 403 JV-D-glucosylglycine ethyl ester, 447 tetra-O-acetyl, 403 D-glucosylhydantoin, 416 3,4-D-Glucoseen, 404 D-glucosylisothiocyanate, tetra-O-ace- A-4,5-D-Glucoseenuronic acid, 719 tyl, 416 Glucose oxidase, 366, 619 iV-D-glucosylnicotinamide, tetra-O- a-Glucosidase, acetyl, 418 almond emulsin, 577 iV-D-glucosylsarcosine amide, 447 maltase, 593 N-D-glucosylurea, 415 industrial value, 563 phenylosazone formation, 415 preparation, 594 reducing power, 415 yeast, aglycon specificity, 595 1-O-glycylglucose, 448 j8-Glucosidase, hydrazones, 80 almond emulsin, 595 SUBJECT INDEX 873

bottom yeast, 593 4-O-methyl, 83, 315 carbohydrate component, 574 1-phosphate, 324 composition, 573 rheumatic diseases, use in, 317 coffee emulsin, 590 D-Glucuronic 3,6-lactone, 317 comparison, various sources, 578, 580 1,2-O-isopropylidene, reduction, 136 enzymic activity, effect of 6-labeled, 136, 317 anions, 573 methyl furanosides, 193 dialysis, 574 0-Glucuronidases, 596 formaldehyde, 574 almond emulsin, 577 pH, 574 biological function, 597 substitution in sugar moiety, 579,580 clinical use, 597 sugar ring size, 581 occurrence, 596 hydrolysis of 0-glucosides, activation Glutose, 63 energies, 573 Glycals, 3, 399 occurrence, 577, 587 halogen addition, 401 specificity, 579 hydration, 400 aglycon, 582, 588, 595 hydrogen halide addition, 401 sugar moiety (rule), 581 hydroxylation, 400 sweet almond, dissociation constants, ozonolysis, 123, 482 566 phenanthraquinone addition, 401 Z-enzyme, 680 preparation, 399 D-Glucosides, properties, 400 2-chloroethyl ß, in vivo synthesis, 599 rearrangement, 401 trichloroethyl ß, in vivo synthesis, 599 synthesis of, enzymic synthesis, 598 aminodeoxy sugars, 470 hydrolysis, cellobiose, 484 acid, compared with enzymic, 587 2-deoxyaldoses, 131 enzymic, effect of glycosides, 202 branching of carbon chain, 583 lactose, 484, 497 chain length, 582 monosaccharides, 127 structural changes in aglycon, 585 Glycamines, see Alditols, 1-amino-l- substitution in aglycon, 584, 586 deoxy hydroquinone ß} 547 Glycans, see Polysaccharides 3-hydroxyindole ß, 543 Glycaric acids, see Aldaric acids o-hydroxymethylphenyl ß, 547 Glyceraldehyde, see Glycerose 6-O-benzoyl, 548 Glyceraric acid, 311 p-methyoxyphenyl ßf 547 D-Glyeerie acid 3-phosphate, 753 methyl ß, naturally occurring, 554 Ώ-glycero-O-galacto-Heptitol, 101, 253 natural, anomeric configuration, 554 D -glycero-D -galacto-Heptose, 62 D-Glucosiduronic acids, utilization, 101 detoxification, 599 O-glycero-O-gluco-Heptitol, 255, 258 oleanolic acid, 546 D-grZî/cero-jS-D-^wZo-Heptopyranose, 1,7- D-Glucosone, see D-ara&ino-Hexosone anhydro, 225 D-Glucurone, see D-Glucuronic 3,6-lac- Glycerol, from sorbitol, 248 tone D-Glycerose, 22 D-Glucuronic acid, 315 dimers, 69 2-amino-2-deoxy-, 466 3-phosphate, 770 1-O-benzoyl, 149 preparation, 124 biogenesis, 317 Rosanoff convention, 21 isonicotinyl hydrazone, 325 L-Glycerose, 124 1,2-O-isopropylidene, 136, 317 D-glycero-O-talo-Keptitol, 102, 253 6-labeled, 136 Glycitols, see Alditols 874 SUBJECT INDEX

Glycine, 5,6-Hexoseens, 404 iV-D-glucosyl, ethyl ester, 447 preparation of osones, 335 Glycine hispida, 0-glucosidase, 588 Glycosidases, 562-601 Glycogens, 714 classification, 562 glycolysis, 767 composition, 573 histochemistry, 638 mechanism, 566-70 isolation, 714 Glycosides, see also Oligosaccharides, occurrence, 714 Polysaccharides and individual phyto, see also Amylopectin, 714 sugars, 3, 189 structure, 714 adrenal corticosteroid, 545 Glycolaldehyde, 69 aglycons related to phenanthrene, "active", 770 543-7 Glycol cleavage, 346 alkali sensitive, 205 anhydroalditols, 396 animal, 560 anomalous resistance, 217, 350 anomeric configuration, 218 disaccharides, 351 determination, 219 effect of structure, configuration, 347 anomerization, 204 formyl esters, formation, 217, 350 effect of aglycon, 204 glycosides, 215 mechanism, 205 kinetics, 348 anthocyanidin, 538 mechanism, 347-8 aryl, 547 "overoxidation",· 216 action of alkali, 221 properties of reagents, 346 diazonium coupling, 450 rate, factors determining, 217 formation of anhydro sugars, acetal reagents, 347 type, 221 Glycolipids, 560, 729 synthesis, 190, 197 Glycolipoproteins, 729 cardiac, 543 Glycolysis, 766 hydrolysis, 544 Embden-Meyerhof-Parnas scheme, 767 influence of sugar moiety, 545 Hexose Monophosphate Shunt scheme, strophanthidin, 545 769, 773 sugars, table, 552 other pathways, carotenoid, 538 Leuconostoc mesenteroides, 774 cyanogenetic, 550 Pseudomonas saccharophila, 774 conformational analysis, 209-10 principal pathways, relative impor- cyclohexyl, 208 tance, 773 role of phosphates, 173 flavanol, 538 Glyconic acids, lactones, see Aldonic from 1,2-anhydro sugars, 204 Glycoproteins, 711, 722-9 function in plants, 536 blood serum, 725 furanosides, nature of proteins, 724 from thioacetals, 200 urine, 726 "gamma", 197 Glycosamines, see Aminodeoxy sugars heterosides, 480 Glycosans, see Anhydro sugars, acetal holosides, 480 type hydrogenolysis, 207 Glycoses, see Saccharides, Sugars hydrolysis, Glycose ammonias, see Glycosylamines acid, 208 Glycoseens, 399, 402 acid and enzymic, rates compared, 1,2-glycoseens, 382 587 hydroxylation, 403 alkaline, 205 preparation, 402, 418 energy of activation, acid, enzyme, reduction, 382 568, 573 SUBJECT INDEX 875

enzymic, direction of bond opening, aldehyde-ammonia structure, 411 569 Amadori rearrangement, 422 factors affecting rate, anomers, 411 aglycon, 208 Af,iV-digly cosy lamines, 408, 413 ring size, 211 from acylglycosyl halides, 416 structure, 209 hydrolysis, 409 selective, enzymic, 598 rate, 418 hydroxyanthraquinone, 551 isomerization, 420 indican, 543 mechanism of formation, 412 isomerization, 204 mutarotation, 420 mustard oil, 555 ninhydrin reaction, 420 naturally occurring, 536-61 nomenclature, 408 nomenclature, 190 nucleosides, 424 of sulfonamides, 415 oxidation, 343, 344 iV-phenyl, 412 catalytic, 466 preparation, 407, 412 uronic acids, 466 reactions, 418 oxygen sensitive, 697 reducing action, 420 plant, reduction, 409 alkyl, 554 ring-chain tautomerism, 409 biochemical determination (Bour- Schiff base structure, 411 quelot method), 600 transglycosylation, 420 enzymic hydrolysis, 554 Glycosyl halides, see O-Acylglycosyl sugar components, 553-4 halides preparation, 190 Glycuronans, see also Hemicelluloses, a-anomers, 198 Pectic substances, 315, 319 aryl (Helferich and Schmitz-Hille- Glycuronic acids, see Uronic acids brecht), 198 Glycuronides, see Glycosiduronic acids properties, 205-12 Glycyrrhinic acid, 319 ring size, determination, Goldenrod, 96 glycol cleavage, 215 Gonadotropic hormones, 728 methylation, 212 composition, 728 saponins, 545 Gossypose, see Raffinose solubility, 205 Graminae, 683 structure, determination, 212-20 fructans, 683 surface active, 206 Graminan, 683 synthesis, 190 Grana, 735 enzymic, 203, 597 Grape juice, 250 in vivo, 599 Grapefruit, 100 Grape sugar, see D-Glucose 1-thio, reductive desulfurization, 383 Grignard reagents, transglycosidation, 204 action on N-Glycosides, see Glycosylamines and aldehydo sugars, 115 individual sugars esters, 115 Glycosiduronic acids, 318, 546, 599 glycosyl halides, 116 hydrolysis, 317 preparation of preparation, 317 2-deoxy-D-en/Mro-pentose, 116 Glycosimines, see Glycosylamines, C-methyl-sq/ZZo-inositol, 285 Ν,Ν-di 1-C-phenylglucosone, 335 Glycosyl, definition, 190 C-substituted alditols, 115 Glycosylamines, 407 Ground substance, 711, 722 Af-acetyl derivatives, 408-10 Guanidine derivatives, 414 876 SUBJECT INDEX

Guanine, 425 Hassel-Ottar effect, 152, 198 iV-D-ribosyl, 84 Hassel-Ottar rule, applied to glyco- Guanosine, 84 pyranosides, 210 diphosphoric acid, 437 Haworth formulas, 38 triphosphoric acid, 437 Haworth reagent, 369 structure, 425 Heart valve polysaccharide, 712 Guaran, 492, 511, 684 Helix pomatia, 88, 474 Guar seeds, galactomannans, 684 eggs, galactan, 716 L-Gulitol, see D-Glucitol £-glucosidase, 589 D-Gulitol, see L-Glucitol Hemiacetals, acyclic, 228 L-Gulonic acid, Hemataminic acid, 475 2-keto, 356 Hemicellulose-A, see Xylans di-O-isopropylidene, 333 Hemicellulose-B, see Hemicelluloses, 2,3-diketo, 332 acidic D-Gulose, 24 Hemicelluloses, 665-72 Gums, acidic, 669 arabic, 85, 685 commercial value, 666 Australian black wattle, 83 nutritional aspects, 799 British, 677 Heparin, 171, 720 cherry, 83 isolation, 720 galactomannans, occurrence, 720 guar, 684 structure, 721 locust, 684 α-Heparin, see Heparin mesquite, 83, 88 /3-Heparin, 720 peach, 83 Heptitols, see also individual com- plant exudates, 684 pounds, 253-4 tragacanth, 685 occurrence, 253 Western larch, 88 Heptoses, see also individual compounds, yeast, 670 45,106 Guncotton, 692 Hesperidin, 539 Gymmema sylvestrej 276 chalcone, 540 Gynaminic acid, see Sialic acid Heterosides, 480 Hevea brasiliensis, 271 H Hexaric acids, see also Aldaric acids and individual compounds, 312 Hagedorn-Jensen method, reducing sug- Hexitols, see also Alditols and individual ars, 616 compounds, 246 Hanes modification, 616 l,4:3,6-dianhydro, 385 Halic acids, 345 Hexosamines, see Hexoses, aminodeoxy Halogeno esters, see Deoxyhalogeno Hexose disphosphatase, 755 derivatives Hexoseens, see also Glycoseens Halogens, as oxidants, 337 5,6-, 404 effect of reductant structure, 340 Hexose Monophosphate Shunt, see also glycosides, 343 Glycolysis, 761, 769 in acid solution, 338 Hexoses, 24, 27 in alkaline solution, 343 aminodeoxy, test, 650 mechanism, 340 anomers, relative reactivity with halo- overoxidation, 339 gens, 340, 342 Hamamelis virginica, 161 biosynthesis, 759 Hamameli-tannin, 161 enzymic interconversion, 760 Hamamelose, 78, 161 Hill reaction, 744-52 Harden-Young ester, 180 Histochemistry, 624-40 SUBJECT INDEX 877

ascorbic acid, 637 gonadotropic, 728 amyloid, 637 thyroglobulin, 728 desulfation, 630 Hudson's Lac tone Rule, 306 enzymes, identification of carbohy- Hyalbiuronic acid, 319, 716 drates, 638 Hyaline cartilage polysaccharide, 712 fixation of tissue, 625 Hyaluronic acid, 318, 319, 716-19 glycogen, Best's carmine stain, 638 biosynthesis, 717 iodine-starch reaction, 626 histochemistry, 633 metachromasia, 626 hydrolysis, enzymic, 718 mucin stains, 627 isolation, 716 nucleic acids, 635 occurrence, 716 deoxyribonucleic acids, 635 structure, 717 Feulgen reaction, 635 Hyaluronidases, 718 methyl green-pyronine stain, 636 clinical use, 718 photometric methods, 636 inhibition, 726 ribonucleic acids, 637 transglycosylation, 720 oxidation methods, vicinal glycols, Hydantoins, 416 627-9 Hydrazine derivatives, 608 boric acid inhibition, 629 1-benzyl-l-phenyl, 609 effect of esterification, 629 p-bromophenyl, 609 indicators, 627 2,4-dichlorophenyl, 609 interfering substances, 629 condensation with sugars, 462 oxidants, 627 diphenyl, 609 periodate-Schiff's reagent methods reaction with aldonic lactones, 462 628 Hydrazones, see Phenylhydrazones sulfite blockade, 628 Hydrides, metal, 261 preparation of sections, 626 Hydrogénation, catalytic reactions of acid groups, 629 reduction of lactones, 310 Alcian Blue 8GS, 634 Hydrogen cyanide, see also Cyanohydrin blocking by proteins, 631 synthesis, combination method, acids and polysaccharides, determination of al- vicinal glycols, 634-5 dehyde and ketone groups, 650 combination with "dialyzed iron", Hydrogen fluoride, 633 epimerization of O-acetyl sugars, 482 extinction point, 630 Hydrogenolysis, metachromasia, 629 benzyl ethers, 368 starch, 638 O-benzylidene compounds, 234 sulfation, 629 epoxides, 393 Hof mann degradation, see Weerman D-glucitol, 248 degradation glycosides, 207 Holosides, 480 Hydrogen peroxide, 357 Homogenizers, hydroxylation of double bonds, 400 carageenan, 686 in glycal synthesis, 127 Homomorphs, 44 oxidation, furanoses, 46 anhydroalditols, 395 pyranoses, 45-6 catalysts, 357, 359-60 Homonataloin, 83 mechanism, 358 Honey, 5, 95, 502 rate, Honeydew, 516 effect of pH, 360 Hormones, effect of temperature, 360 878 SUBJECT INDEX

starch, 699 5-Hydroxymethylfurfural, see 2-Furalde- sugars, 357 hyde, 5-hydroxymethyl use in degradation, 118 5-Hydroxymethylfuroic acid, see 2-Fu- Hydrogen sulfide, roic acid, 5-hydroxymethyl in photosynthesis, 742 4-Hydroxypyrolline-2-carboxylic acid, reductive denitration, 694 731 Hydrogen transport, 437-40 Hydroxymytilitol, see scyllo-Inositol, coenzymes, 437-40 hydroxymethyl Hydroglucal, see 2-deoxy-D-ara6mo- Hypobromite, hexitol, 1,5-anhydro oxidation of anhydroalditols, 395 Hydrol, 93 Hypohalites, see also Halogens, as oxi- gentiobiose, 493 dants, 337 Hydrolysis, see also general listings, e.g., conversion to halates, 338 Acetates, Esters, Ethylidene, Hypoiodite, see Iodine as oxidant etc.y and individual compounds Hypoxanthine, 425 acetals, 237, 390 I ΛΓ-acetyl, 410, 463, 650 anhydro compounds, 390 Idaein, 88 esters, 139, 196 D-Iditol, 251 ethers, 368, 375, 509 L-Iditol, 251 glycosides, 208, 568, 587 l,4:3,6-dianhydro, 385 glycosylamines, 409, 418 D-ido-Heptulose, nitrates, reductive, 165 enzymic synthesis, 759 nucleic acids, 425, 441 D-Idose, 24 oligosaccharides, 490 1,6-anhydro, 222 phenylosazones, 334, 459 L-Idose, phosphates, 177 6-deoxy-6-nitro, 273 polysaccharides, 701 L-Iduronic acid, 719 sulfates, 170-1 Illicium religiosum, 278 uronic acids, 319, 718 Illicium verum, 278 thioacetals, 199 Indican, 543 Hydroxamic acid, 308 Indoxyl, 543 Hydroxyanthraquinone glycosides, 551 Infrared spectra, Hydroxycinnamic alcohols, 548 anomeric configuration, 41 enzymic dehydrogenation, 548 polysaccharides, nature of glycosidic (dextro) -11 -Hy droxyhexadecanoic acid, linkages, 654 99 Schiff bases, 411 Hydroxyglycals, see 1,2-Glycoseens Inosine, 425 Hydroxyisomytilitol, see myo-Inositol, Inosinic acid, 432 2-hydroxymethyl Inositol, see Inositols and sterically Hydroxylamine, 452 individual compounds listed polysaccharides, determination of al- below dehyde and ketone groups, 650 ß-Inositol, see D-Inositol sugar oximes, 462 d-Inositol, see D-Inositol Hydroxyl groups, D-Inositol, 270 assay, 140 configuration, 282 primary, quantitative estimation, 164 5-O-methyl, 270 primary-secondary, identification, 164 L-Inositol, 271 Hydroxymalonic acid, see Glyceraric configuration, 282 acid 1-O-methyl, 271 3-Hydroxy-4-methoxybenzoic acid, 287 DL-Inositol, 271 SUBJECT INDEX 879 t-Inositol, see mj/o-Inositol Acetobacter suboxydans oxidation, 288 aZ/o-Inositol, 277 conformational requirements, 289 configuration, 283 O-alkylation, 295 synthesis, 277 alkylidene formation, 295 epi-Inositol, 279 aromatization, 293 D-1 ,3-dideoxy-epz'-inositol-2-carboxylic configuration, 279 acid, 278 proof, 279 configuration, 286 tetrahydroxybenzoquinone, 279 structure, 286 monodeoxy, 274 synthesis, 279 preparation, 276 meso-Inositol, see rat/o-Inositol dideoxy, 276 rawco-Inositol, 275 dialdoses, preparation, 335 configuration, 283 esterification, 294 D-1-deoxy, 274 formulas, 269 configuration, 282 halohydrins, 292 synthesis, 278 inversions, 293 rat/o-Inositol, 271 diketo, 290 basic lead acetate complex, 295 metal complexes, 295 biochemical oxidation, 134 nomenclature, 268 biosynthesis, 296 oxidation, catalytic, 289 configuration, 280 monophosphates, 294 D-1-deoxy, 276 reactions with configuration, 282 bromine, 291 L-1-deoxy, 276 glycol splitting agents, 292 2-deoxy, 276 hydrohalic acids, 292 l-O-(a-D-galactosyl), 274 hypobromite, 291 2-hydroxymethyl, 278 nitric acid, 290 configuration, 284 permanganate, 291 L-l,2-diketo, 290 rhodizonic acid, 279 metabolism, 297 Scherer test, 280 2-methyl, 284 structure, 279 configuration, 284 proof, 279 5-O-methyl, 274 synthesis, 1,3-di-O-methyl, 274 from sugars, 272 2-phosphate, 294 total, 280 phytic acid, 271 d-Inosose, see L-ra^o-Inosose vitamin activity, 296 D-epz-Inosose-2, 289 neo-Inositol, 279 DL-ept-Inosose-2, 279 2-amino-2-deoxy, 298 epi-meso-Inosose, see DL-epz-Inosose-2 synthesis, 279 D-mi/o-Inosose-l, 289 L-myo-Inosose-l, 276, 289 scyllo-Inositoly 274 raî/o-Inosose-2, 273, 274 diaminodideoxy, 297 configuration, 281 configuration, 281 penta-O-acetyl, 285 diguanidino, 558 action of Grignard reagent, 285 hydroxymethyl, 278 scyllo-meso-Inosose, see ra2/o-Inosose-2 configuration, 284 Inososes, see also individual compounds, methyl, 278 134, 289 configuration, 284 aromatization, 296 synthesis, 285 osazones, 290 Inositols, 268 preparation, 288-90 880 SUBJECT INDEX

Acetobacter suboxydans, 288 dialyzed, histochemistry, 633 catalytic oxidation, 289 Hill reaction, 744 reactions, 296 Ruff degradation, 118 Inulases, 593, 683 Irpex lacteus, jS-glucosidase, 589 Inulin, 96, 683 Isoalloxazine derivatives, 413 triacetate, 156 Isoamylase, 683 D-glucose, 684 Isobarbaloin, 83 hydrolysis, enzymic, 592, 683 Isocyanates, 416 sucrose, 684 glycosylureas, 416 synthesis, 707 urethans, 416 Inulobiose, 533 Isodulcit, see L-Mannose, 6-deoxy Inversion, Isoflavones, 538 configurational, see Waiden inversion D-Isoglucal, 402 sucrose, 96, 505 Isoglucosamine, see D-Fructose, 1-amino- Invertase, see ß-Fructofuranosidase, 1-deoxy Yeast emulsin Isohexides, see Hexitols, l,4:3,6-dian- Invert sugar, 505 hydro Iodic acid, 345 Isomaltose, 493 specificity as oxidant, 345 octa-O-acetyl, 495 Iodide, replacement of sulfonate groups, anomerization of octa-O-acetyl gen- 164, 397 tiobiose, 495 Iodine, occurrence, 494 as oxidant, preparation, 494 aldoses, quantitative estimation, structure, 494 343, 617 synthesis, alkaline solution, 343 biochemical, Pénicillium chryso- polysaccharides, determination of al- genum, 534 dehyde and ketone groups, 649 gentiobiose, 494 iodine-starch reaction, D-glucose in acid, 494 achroic point, 681 Isomaltotriose, 520 amyloid, 638 Isomannide, see D-Mannitol, 1,4:3,6- amylose, 676 dianhydro amylopectin, 676 Isomytilitol, see myo-Inositol, 2-methyl glycogen, 714 Isoprimeverose, see D-Glucose, 6-O-a-D- histochemical application, 626, 638 xylosyl Ion-exchange resins, see also Chromatog- Isopropylidene derivatives, 158, 236 raphy, absorption, 239 Chromatographie techniques, 603 glucose production, commercial, 91 hydrolysis, 237 glycoside formation, 193 structure, 238 reversion, polysaccharide hydrolysis, utilization, 239 708 Isorhamnetin, 539 separation of sugars and derivatives, D-Isorhamnose, see D-Glucose, 6-deoxy 602 Isorhodeose, see D-Glucose, 6-deoxy Ionophoresis, Isorotation Rules, 72 borates, 172, 604 O-acylglycosyl halides, 151 Ipomoea orizabensis, 99 aminodeoxy sugars, 467 Irideae laminarioides, 135 glycosides, 218 Irisan, 683 structure of Irish moss, 685 isomaltose, 494 Iron, sugars, general, 74 SUBJECT INDEX 881

Isosaccharic acid, see D-Mannaric acid, Koenigs-Knorr reaction, 194 2,5-anhydro kinetics, 194 Isosaccharinic acid, 67 neighboring group participation, 194 Isosorbide, see D-Glucitol, l,4:3,6-dian- orthoester formation, 194 hydro synthesis, Isosucrose octaacetate, 506 glycosides, 191 Isothiocyanates, 416 oligosaccharides, 483 Isotope labeled sugars, see also indi- a-anomers, 483 vidual sugars, 135, 622-4, 752 mercuric acetate catalysis, 483 degradation, 622 pyridine catalysis, 483 procedures, 135 quinoline catalysis, 483 synthesis, 622 Kojic acid, 404 Isovanillic acid, 287 Krebs cycle, 777 Ivy berries, 88 Kritesan, 683

Jalap resin, 99 Labiose, 520 Jellying power, see Gelation Lactaminic acid, see Sialic acid Jerusalem artichoke, 96 Lactarius volemus, 253 L-Lactic acid, 28 fructans, 683 from sugars in alkali, 66 kestose, 532 glycolytic production, 767 Lac tides, 305 Lactobacillus species, 85 Kaempferol, 511 L. acidophilus, 789 Kerasin, 560 L. casei, 622 Keratosulfate, 722 labeled glucose, fermentation, 622 occurrence, 722 L. pentosus, 761 Kestose, 531 Lactobionic acid, 496 Ketazines, 462 Lactoflavin, see Riboflavin keto Forms, see also aldehydo, acyclic, Lactone rule, 306 54, 144 Lactones, see also Aldonic, Aldaric, and Ketoses, see also individual sugars, 27 Uronic lactones, and individual action of bromine, 339 compounds configurations, 27 Angelica, 58 1-deoxy-l-halo, 172 Lactose, 495 1-deoxy-l-p-toluino, 422 effect on intestinal microflora, 789 reduction, 422 hydrolysis, 496 diketose dianhydrides, 224 acid, conditions, 498 epimerization in alkali, 62 identification, 495 preparation, nutritional aspects, 789 biochemical oxidation, 132, 265 adaptation, 791 diazomethane synthesis, 111 anomers, 790 epimerization of aldoses, 60-2 cataractogenic action, 792 oxidation, electrolytic, 264 effect on calcium and phosphorus Seliwanoff test, 608 utilization, 794 separation from aldoses, 602 galactosemia, 794 Keturonic acids, see Aldonic acids, laxative effect, 791 5-keto occurrence, 495, 789 Kiliani-Fischer synthesis, see Cyanohy- preparation, 496 drin synthesis properties, 495 882 SUBJECT INDEX

structure, 496 Lévulose, see D-Fructose synthesis, 496 Lignin, 660 enzymic, 497 digestibility, 798 tolerance, human, 498 Lignoceric acid, utilization, 790 Δ16, 560 influence of glycosidic linkage, 790 2-hydroxy, 560 Lactose 1-phosphate, 184 Limacoitin sulfate, 724 Lactulose, 481 Lindane, 297 Lagenaria leucantha, 599 α-Lipoic acid, 747 Laminaran, 511, 687 biological form, 751 resistance to periodate, 700 effect of light, 750 Laminaria cloustoni, 278, 687 Lipothiamide pyrophosphate, 746 Laminaribiose, 511 Lithium aluminum hydride, Laminitol, 278 O-acylglycosyl halides, 383 Lanata-glycoside C, 544 epoxides, hydrogenolysis, 393 Lane and Eynon method, reducing sug- Lobry de Bruyn-Alberda van Eksnstein ars, 615 transformation, 60-2 Lanthanum, catalytic hydrolysis, nu- mechanism, 61 cleic acids, 426 Loco weed, 270 Larch, Lucerne, see Alfalfa €-galactan, 510 Lupeose, see Stachyose gum, 511 Lupinus lutens, 519 Larix occidentalis, 511 L-Lyxoflavin, 425 Laurus per sea L., 253 L-Lyxose, 24 Lead hydroxide, 426 5-deoxy-3-C-formyl, 558 Lead tetraacetate, 347 nucleoside-like compounds, 425 active méthylène groups, 351 M glycol cleavage, 217 anomalous reaction, thioacetals, 351 MacDonald-Fischer degradation, 121 glycosides, 217 Macrocystis pyrifera, 687 polysaccharides. 648 Madagascar manna, 251 lower aldoses, preparation, 123 Madder, 551 LeBel-van't Hoff Theory, 8 glycosides, 552 Legumes, galactomannans, 684 Madder root, 512 Lemon flavin, 100 Magnesium oxide, catalytic hydrolysis of Lengthening carbon chain, see Carbon nucleic acids, 425 chain, lengthening Main's "pot method", reducing sugars, 615 Lentils, 519 L-Malic acid, 311 Leucoanthocyanins, 539 photochemical production, 748 Leuconostoc species, polysaccharides, 688 Malic enzyme, 748 Leuconostoc mesenteroides, 688 Maltase, see a-Glucosidase, yeast labeled glucose, fermentation, 623 Maltobionic acid, 499 sucrose synthesis, 521 Maltose, 498 Leucrose, 534 absorption, 783 Levan, 530, 683, 706 conversion to isomaltose, 534 Levan-sucrase, 706 identification, 498 Levoglucosan, see D-Glucose, 1,6-anhy- nutritional aspects, 784 dro occurrence, 498 Levulinic acid, 58 preparation, 499 formation, mechanism, 59 properties, 498 SUBJECT INDEX 883

structure, 499 occurrence, 249 aldobionic acid method, 499 synthesis, 249 anomeric configuration, 500 DL-Mannitol, 250 methylation method, 499 synthesis, total, 250 Maltotetraose and higher oligosaccha- L-Mannitol, 250 rides, 514 D-Mannofuranuronic 3,6-lactone, 324 Maltotriose, 513 Ό-manno -Heptulose, 101 identification, 514 hexa-O-acetyl-a, 81 occurrence, 514 hydrazones, 81 properties, 513 nutritional aspects, 796 structure, 514 occurrence, 101 "Maltulose", from glycogen, 715 preparation, 101 Malvus species, 500 utilization, 101 Mammary tissue enzymes, 497 D-Mannoketoheptose, see D-mawno-Hep- Manna, tulose Douglas fir, 516 L-Mannomethylose, see L-Mannose, 6- larch, 516 deoxy Virginia pine, 516 D-Mannonic acid, Manna ash, 249 2,5-anhydro, 379 Mannans, 669 1,4-lactone, 250 salep, 670 D-Mannopyranoside, vegetable ivory, 669 ethyl l-thio-jS, 201 D-Mannaric acid, 313 methyl, 2,5-anhydro, 379 a, ethanethiolysis, 201 Mandelonitrile, ß, ethanethiolysis, 201 amygdalin, 550 2,3:4,6-di-0-isopropylidene, 237 prunasin, 551 D-Mannose, 94 sambunigrin, 551 configuration, 20 Manneotetrose, see Stachyose occurrence, 94 Manninositose, 272 nutritional aspects, 788 Manninotriose, 514 preparation, 94 from stachyose, 519 synthesis, total, 103 identification, 515 utilization, 95 occurrence, 515 D-Mannose derivatives, preparation, 515 3,4,6-tri-O-acetyl-0, l,2(methyl ortho- properties, 515 acetate), 196 structure, 515 2-amino-2-deoxy, 380, 469 D-Mannitol, 249 2,5-anhydro, 378, 468 1,4-anhydro, 385 1,6-anhydro-0-D-mannopyranose, 221 1,5-anhydro, 382 calcium chloride, 95 l,4:3,6-dianhydro, 164, 385 2,3:5,6-dicarbonate, 159 conversion to dichlorodideoxy com- 4-0-/3-D-galactopyranosyl, 484, 497 pound, 396 6-O-a-D-galactopyranosyl, see Meli- 2,5-O-methylene, 390 biose hydrazones, 80 l,5:3,6-dianhydro, 385 2,3:5,6-di-0-isopropylidene, 237 borates, 263 D-mannofuranosyl chloride, 2,3:5,6- boric acid, effect on acidity, 263 dicarbonate, 159 1-deoxy-l-p-toluino, 422 4-0-/3-D-mannopyranosyl, 511 1-O-a-D-galactopyranosyl, 501 sî/m-D-mannosylguanosine 5'-pyro- nutritional aspects, 796 phosphoric acid, 95 884 SUBJECT INDEX

D-mannosylstreptomycin, 558 aldobionic acid method, 500 6-diphenylphosphate, 2,3,4-tri-0- methylation method, 500 acetyl-a, 184 synthesis, 483, 501 1-phosphate, 174 Koenigs-Knorr, 501 1,6-diphosphate, 184 Melitriose, see Raffinose D-Mannoside, Melibiulose, see Planteobiose D-glyceric acid, naturally occurring, Menadione, 757 554 Mercaptals, see Thioacetals and indi- L-Mannose, 6-deoxy, (L-rhamnose) 100 vidual sugars 4-O-D-glucopyranosyl, 511 Mereaptans, see Thiols and individual hydrazones, 81 compounds 3-O-methyl, 552 Mercaptolysis, 201 nutritional aspects, 796 structure studies, 202 occurrence, 100 Mercerization, cellulose, 663 phenylosazone, 81 Mercuric acetate, preparation, 100 Koenigs-Knorr synthesis, a-anomers, quercitrin, 539 483 a-Mannosidase, oligosaccharides, synthesis, 483 alfalfa emulsin, 577, 590 Mercuric oxide, bottom yeast, 593 2-amino-2-deoxyaldoses, oxidation, 472 coffee emulsin, 590 meso Compounds, 11 Mannosylstreptomycin, 558 Mesothelioma polysaccharide, 712 D-Mannuronan, alginic acid, 687 Mesoxaldehyde bis (phenylhydrazone), Mannurone, see D-Mannofuranuronic 623 3,6-lactone Mesquite gum, 83, 88 Maple sap, 502 Mesylates, see Methanesulfonates Matezodambose, see D-Inositol Metachromasia, 626, 631-3 Medicago sativa, 590 abolition by ''methylation", 632 Meerwein-Pondorff reaction, 292 effect of polymerization, 632 Melampyrum nemorosum, 252 induction in neutral polysaccharides, Melanoidin reaction, 406, 446 632 mechanism, 447 Metasaccharinic acid, 68 Melezitose, 515 degradation, 87 identification, 516 2-deoxy-2-er2/iÄro-pentose, 87 nutritional aspects, 795 Methacrylic anhydride, 163 occurrence, 516 Methanesulfonates, 163 preparation, 516 replacement, secondary, 172 properties, 516 Methose, 103 structure, 516 Methoxyformates, 158 turanose, 508 O-Methylation, alkyl iodide-silver oxide method, 370 Melibiase, see a-Galactosidase, bottom alkyl iodide-sodium alkoxide method, yeast 370 Melibiitol, 501 determination of glycoside structure, Melibiose, 500 31 from raffinose, 517 diazomethane, 371 identification, 500 dimethylsulfate method, 369 nutritional aspects, 796 of occurrence, 500 acids (esterification), 632 preparation, 500 disaccharides, 487 properties, 500 glycosides, 212 structure, 500 polysaccharides, 653 SUBJECT INDEX 885

branch-unit assay, 651 configuration, 24-5 end-group assay, 651 use of alditols, 258 estimation of hydroxyl groups, identification, 602, 652, 713 648 interconversion, biochemical, 775 nature of glycosidic linkages, 653 keto, Schiff's reaction, 144 resistant hydroxyl groups, 696 naturally occurring, 80 partial, 370 structure, 258 thallous alkoxide method, 371 Mountain ash berry, 98, 132 Methyl chloroformate, 158 Mucic acid, see Galactaric acid O-Methyl determination, 650 Mucicarmine stain, 635 Méthylène blue, reducing sugar test, 608 Mucihematein stain, 635 Méthylène derivatives, see also indi- Mucin, 711 vidual compounds, 232 funis, 723 acetolysis, 232 gastric, 724 formation, 232 isolation, 724 rules, 231 polysaccharides, 725 structure, 232 histochemistry, 627 Methyl ethers, Alcian Blue 8GS, 634 degradation, oxidative, 214 dialyzed iron, binding, 633 distillation, 602 salivary, 726 Methylfurfural, see 2-Furaldehyde, 5- composition, 727 methyl isolation, 726 Michaelis constant, 565 synovial fluid, 723 Michael synthesis, 190, 197 Mucoids, Microorganisms, identification, 622 blood serum, 725 Mildew, 664 composition, 725 Milk sugar, see Lactose ovomucoid, 728 Mistletoe berries, 271 urinary, 726 Molar frictional coefficient, 657 composition, 726 Molecular weight determination, poly- Mucoitin sulfates, 712 mers, 655 Mucoproteins, 722-9 osmotic pressure method, 656 proteins, nature, 724 sedimentation equilibrium procedure, Mucosin, 717 657 Mucus, 711 sedimentation velocity procedure, 656 Mushrooms, 425 viscometric method, 694 Mushroom sugar, see Trehalose Mustard seed emulsin, 600 Molisch test, 607 Mutarotase, 50 Molybdic acid, molybdates, Mutarotation, 29, 49-57 complexes, 262 penta-O-acetyl -aldehydo-hexoses, 145 effect on rotation, 259 activation energies, 52 Monilia yeast, 86 coefficients, 52 Monosaccharides, see also Aldoses, complex, 51 Ketoses, Sugars, and individual effect of pH, 55 compounds, 2 enzymic catalysis, 50 aldehydo, equations, 50, 52 penta-O-acetyl, mutarotation, 145 generalized acid-base catalysis, 55 Schiff's reaction, 144 D-glucose, 53 biosynthesis, 758-62 N-glycosylamines, 420 branched chain, naturally occurring, kinetics, 55-7 78 lactones, 306 classification, 4 oligosaccharides, 488 886 SUBJECT INDEX

oximes, 463 decomposition mechanism, 170 phenylhydrazones, 454 instability, 169 phenylosazones, 459 polysaccharides, 693 L-ribose, 53 denitration, 693 D-talose, 53 preparation, 169 Mycarose, 78 primary, replacement of halogen or Mycodextrans, 706 sulfonate, 169 Mycose, see Trehalose reductive denitration, 170 My rosin, 555 reductive hydrolysis, 165 Myrtillin, 88 saponification, 170 Mytilitol, see sq//Zo-Inositol, methyl Nitric acid oxidation, see also Nitrogen M y Ulis edilis, 278 dioxide, methylated saccharides, 212-214, 353 N polyols, 246, 290 saccharides, 313, 353 Nataloin, 83 Naphthoresorcinol test, products, 354 D-gluconic acid, 2-keto, 327 vanadium pentoxide catalysis, 353 uronic acids, 318 C-Nitroalcohols, see also Nitromethane Naringin, 100 synthesis, 131 2-deoxyaldose preparation, 131 Nebularine, 425 Nitroethanol synthesis, see also Nitro- Neisseria meningitidis, phosphorylase, methane synthesis, 111 527 preparation of, Neisseria perflava, amylosucrase, 705 D-grfo/co-heptulose, 111 D-Neogalactide, see D-Galactitol, D-manno-heptulose, 101, 111 l,5:3,6-dianhydro Nitrogen dioxide oxidation, 354 Neokestose, 532 mechanism, 355 Neolactose, see D-Altrose, 4-Ο-β-Ώ- polysaccharides, 699 galactosyl specificity, 354 Neomannide, see D-Mannitol, 1,5:3,6- Nitromethane synthesis (Sowden- dianhydro Fischer), 109 Neomycin, 297 for lengthening carbon chain, 109 Neosorbide, see D-Glucitol, 1,5:3,6- preparation of, dianhydro O-erythro-L-manno-octose, 110 Nervone, 560 L-glucose, 110 Neuberg ester, 181 L-gulose, 110 Neuraminic acid, see also Sialic acid, heptoses from D-mannose, 110 475 L-mannose, 110 gangliosides, 560 C-nitrodeoxyinositols, 110* Neurospora crassa, 471 separation of epimers, 109 pectinase, 672 Nitrophenols, reducing sugar tests, 608 Niacin, see Nicotinic acid Nitrous acid, Nickel, see Raney nickel anhydro derivatives, formation, 378 Nicotinamide, 418 ,437,745 deamination, 378 JV- (tetra-O-acetyl-D-glucosyl), mechanism, 380 1,2-dihydro, 418 Nomenclature, 1,6-dihydro, 418 D- and L, 21 Nicotinic acid, requirement in fructose selection of reference group, 23 metabolism, 787 higher carbon sugars, 44-9 Nigeran, 706 oligosaccharides, 480 Nitrates, 168 Nonitols, 257 O-acylglycosyl nitrates, 169 Notatin, 366 SUBJECT INDEX 887

Nucleic acids, see also Ribonucleic acids, nomenclature, 480 Deoxyribonucleic acids, 84,441-6 plants, determination, Bourquelot genetic implications, 445 method, 600 histochemistry, 635 primers, polysaccharide synthesis, hydrolysis, 441 703-4 catalysts, 425 reducing, non-reducing, 480 isolation, 441 structure, 487-9 occurrence, 441 enzymic method, 488 structure, 442 anomeric configuration, 488 Nucleoproteins, 635 methylation method, 487 Nucleosides, 424 mutarotation, significance, 488 diphosphoric acids, 435, 437 oxidation procedures, triphosphoric acids, 435, 437 aldonic acids, 487 phosphorylated, see Nucleotides periodate, 488 preparation, 425 preparation of simpler oligosac- separation, 426 charides, 488 structure, 426 synthesis, 481 anomeric configuration, 428 alkaline rearrangement, 481 point of attachment, sugar to base, anomeric rearrangement, 483 428 condensation of monosaccharides, sugar-ring size, 427 486 synthesis, 429 degradation, 482 enzymic, 426 dehydrating agent, 487 Nucleotides, 430, 746 ω,α/oligodeoxy compounds, 483 acid-labile phosphate, 432 enzymic, 486, 520-35 acid-stable phosphate, 432 from anhydro sugars, acetal type, diphosphopyridine (DPN), 437, 745 483, 485 triphosphopyridine (TPN), 438, 745 from polysaccharides, nature of related substances, glycosidic linkages, 654 B-group vitamins, 437 glycal method, epimerization, 481 coenzymes, 437 thermal condensation, 485 structure, 431 Waiden inversion, 482 preparation, 430 Olive tree, 249 separation, 430, 431 Onion, scorodose, 520 Nylon, 666 Open-chain forms, see aldehydo, keto, and individual sugars O Opepe wood, 274 Opium poppy, 0-glucosidase, 588 Oak galls, 161 Optical rotation, see also Mutarotation, Octitols, 256 Polarimetry, and Saccha- Okra mucilage, 510 rimetry, 610-12 Oldham and Rutherford rule, 164 alditols, 258 Olea fragrans, 554 enhancement by complex formation, Oleanolic acid D-glucosiduronic acid, 546 259 Oligosaccharides, 478-535 direct polarization, 611 homologous, 479 glycosides, influence of aglycon struc- variations of properties with degree ture, 75 of polymerization, 479 polysaccharides, nature of glycosidic hydrolysis, acid, 490 linkages, 653 rates, 489 specific rotation, 51 naturally occurring, 490-535 Optical superposition, principle, 70 888 SUBJECT INDEX

Orchidaceae, 94 aldononitriles preparation, 464 Orcinol, quantitative determination of degradation, 122 sugars, 608, 617 mutarotation, 463 Orthoacetates, 195 reduction, 475 Orthobenzoates, 149 Oxycellulose, see Cellulose, oxidation Orthoesters, Oxygen acyl migration, 147 degradation of, control of formation, 198 glycosides, 316 hydrolysis, 196 sugars, 356 structure, 196 dehydrogenation, catalytic, 356 test for, 195 platinum, 356 Orthosaccharinic acids, see Aldonic sodium ferropyrophosphate, 357 acids, 2-deoxy enzymic catalysis, 366 Osazones, see Phenylosazones glycol cleavage, 218 Osmic acid, 253 oxidation of Osmium tetr oxide, hydroxylation of alditols, 264 double bonds, 400 isopropylidene derivatives, 316 Osmotic pressure, molecular weight of sugars, 122 polysaccharides, 656 glycosides, 316 Osones, 134, 333 uronic acids, preparation, 316, 357 preparation, 334 Ozone, degradation of glycals, 123, 482 from anhydroalditols, 395 from glycoseens, 335 P via Grignard reaction, 335 reducing action, 334 Panose, 520, 533 structure, 334 Papaver somniferum, /3-glucosidase, 588 Osonic acids, see Aldonic acids, 2-keto Parsley, 553 Osotriazole, see Phenylosotriazoles Passion fruit (Passiflora edulis), 98 Osseomucoid, 723 Pastes, 675 Ovomucoid, 94, 728 Pavy method, reducing sugars, 615 composition, 729 Peach, /3-glucosidase, 588 isolation, 728 Peach gum, 83, 510, 512 Oxazolines, Pear wood, xylan, 668 from doses, 474 Pecan shells, 85 Af-acetyl-2-amino-2-deoxyal-At - hydrox- Pectases, 671 yglycoxazolines, 417 Pectic acid, 671 μ-thiolglycoxazolines, 417 Pectic substances, 670 Oxidants, 336, 361 arabans, 671 Oxidation-reduction potential, biologi- composition, 671 cal compounds, 746 gels, formation, 671 Oxidations, 299-366 isolation, 670 alditols, 264 nutritional aspects, 799 biological, 364 occurrence, 670 role of phosphates, 173 sugar beet, 138, enzymic, 366 Pectin, see Pectic substances inositols, 280, 290 Pectinases, 671 polysaccharides, 696 Penicillin B, 366 Oxidative pathway, see Hexose Mono- Pénicillium species, 365 phosphate Shunt P. chrysogenum, 534 Oximes, isomaltose formation, 534 acetates, 143 P. glaucumf 366 SUBJECT INDEX 889

Pentaric acids, see also individual acids, Permanganate oxidation, 291, 362 312 effect of pH, 363 Pentasaccharides, 513-20 Persea gratissima, 101 Pentitols, see also individual compounds, Perseitol, see O-glycero-D-galacto-Hep- 243 titol total synthesis, 244 Phaseomannite, see ra^o-Inositol Pentoses, see also individual sugars, Phenanthrene, aglycons related to, biosynthesis, 760 543-7 interconversions, 776 adrenal corticosteroid glycosides, 545 phloroglucinol test, 608 cardiac glycosides, 543 quantitative determination, 619 saponins, 545 Tauber's benzidine test, 607 solanum alkaloids, 546 Peonin, synthesis, 538 Phenylboronic esters, 172 Perbenzoic acid, oxidation of glycals, o-Phenylenediamine, 609 127, 400 benzimidazole formation, 413 Perchloric acid, condensations with acetylation catalyst, 140 acids, 414 anomerization of glycosides, 204 glucose, 413 Perillaldehyde-a-emfo'-oxime, 97 osones, 414 Periodate oxidation, 347, 362 Phenylhydrazides, 415 acetamido group, effect, 217 Phenylhydrazine, 452, 609 condensation with acids, lactones, anomeric configuration studies, 427 glycosides, 219 salts, 415 eis, trans hydroxyls, influence on rate, polysaccharides, determination of al- 285 dehyde and ketone groups, 649 end-group assay, 650 substituted, specific reactions, 453 glycol cleavage, Phenylhy drazones, electrolytic method, 352 decomposition, 453 kinetics, 348 enantiomorphs, resolution, 90 mechanism, 348 formation, 452 resistant structure, 350 mutarotation, 454 . stoichoimetry, 349 diphenylformazans, 455 quantitative determination of sugars, histochemical oxidations, 628 metachromasia, induction, 632 619 over oxidation, 292 rate of formation, 453 oxidation of dependence on sugar structure, 453 active méthylène groups, 351 structure, 453 labeled sugars, 622 Phenyl isocyanate, 160 polysaccharides, Phenylosazones, 455 anhydro derivatives, 387 nature of glycosidic linkages, 653 conversion to estimation of vicinal hydroxyl osones, 459 groups, 648 phenylosotriazoles, 460 preparation of lower aldoses, 123 formation, 455 structure determination, mechanism, 456 anhydro sugars, acetal type, 223 from glycosides, 31, 215 2-amino-2-deoxyaldoses, 458 oligosaccharides, 488 2-chloro-2-deoxyaldoses, 458 polysaccharides, 699 2-deoxy-2-methoxyaldoses, 458 reduction and hydrolysis of oxida- hydrolysis, 334, 459 tion products, 654 identification of sugars, 458 890 SUBJECT INDEX

mechanism of formation, 456 Phosphorus pentabromide, scission of mutarotation, 459 anhydro rings, 172 diphenylformazan formation, 460 Phosphorus pentachloride, action on quantitative determination of sugars, sugar acetates, 156 619 Phosphorus oxychloride, transglycosida- reduction, 461, 619 tion, 204 structure, 459 Phosphorylases, 520 Phenylosotriazoles, 609 isolation from potato, 683 formation, 460 polysaccharide synthesis, 704-5 isolation, 609 Photosynthesis, labeled, degradation, 624 "active hydrogen", nature, 744 structure of oligosaccharides, 489 apparatus in plants, structural as- Phenyl phosphorodichloridate, 174 pects, 734 Diphenyl phosphorochloridate, 174 bacterial, 742 Phillyrin, 554 Blackman reaction, 739 Phlean, 683 carbon dioxide fixation, 752-7 Phloroglucinol test, 608 D-eri/JÄro-pentulose diphosphate, Phoenix canariensis, 94 183, 753 Phosgene, 159 other acceptors, 757 carbonate esters, 158 carbon, distribution, 752-7 Phosphate esters, 138, 172 early labeled products, 752, 754 absorption of monosaccharides, 781 "comparative biochemistry", 743 dibenzyl phosphochloridate method dark reaction, 739 174, 436 effect of cyclic, 176 carbon dioxide concentration, 737 dissociation constants, 173 interaction of factors, 739 light intensity, 737 enzymic synthesis, 175 light quality, spectral, 737-8 high energy bonds, 749 temperature, 739 hydrolysis, 177 generalized formulation, 742 constants, 178 high energy phosphate bonds, produc- mechanism, 179 tion, 749 relative ease, 177 Hill reaction, 744 migration, 175, 432 hydrogen transport, 745 of compounds involved, 745 3-carbon carbohydrate metabolites, kinetics, 736 187 mechanism, 743 optical rotations, 187 phosphorylation, 756 3-carbon sugars, 184 pigments, 740-1 hexoses, 180, 185-6 biosynthesis, 742 isolation, 180 light energy, mode of transfer, 741 naturally occurring, 179 respiration, photoeffect, 737 monosaccharides, rotations, 185-6 role of phosphates, 173 oxidative phosphorylation, 778 Phrenosin, 560 ribonucleic acid synthesis, degrada- Phytase, 271 tion, 177 Phytelephas macrocarpa, 94, 221 synthesis, 174 Phytic acid, 271 Phosphopentoisomerase, 755 Phytin, 271 Phosphopentokinase, 755 Phytoglycans, see Polysaccharides, Phosphorus, utilization, effect of dietary phyto lactose, 795 Phytoglycogen, see Amylopectin SUBJECT INDEX

Phytomonas tumefaciens, 690 acetates, 692 Phytopolysaccharides, see Polysaccha- algal, 686-8 rides, phyto alkaline cleavage, 698 Picea rubra, 270 O-alkylation, 695 Picrocrocin, 207, 542 animal, 709-32 Pikromycin, 465 classification, 710 Pinitol, see D-Inositol, 5-O-methyl distribution, 709, 712 Pinus lambertiana Dougl., 270 histochemistry, 606 Plane tree, 249 nomenclature, 710 Plantago species, 517 pathologies, 709 P. ovata, 517 bacterial, 688-708 Planteobiose, 501 carbamates, 695 occurrence, 501 classification, 642 properties, 501 depolymerization, 701 structure, 501 esterification, 691-5 synthesis, 501 impelling agents, 695 Planteose, 516 ethers, industrial, 695 identification, 517 fungal, 688-90 occurrence, 517 general aspects, 641-59 preparation, 517 histochemistry, 606 properties, 517 hydrolysis, acid, 701 structure, 517 effect of structure, 702 Plasma volume expander, 688 reversion, 702 Platinum oxide, catalytic dehydrogena- solubility, 702 tion, 264, 356, 466 mixed esters, 695 preparation of uronic acids, 466 nitrates, 693 Pneumococcus species, commercial preparation, 693 capsular substances, metachromasia, denitration, 693 632 viscometry, 694 polysaccharides, 451, 690 nomenclature, 641 antigenic activity, 690 oxidation, 696-701 composition, 690 oxidative depolymerization, structure, 690 selective, 699 Poan, 683 plant exudates (gums), 684-6 phytopolysaccharides, 659-88 Poison ivy, 100 pneumococcal, 451, 690 Polarimetry, see also Optical rotation, purification, 646 Saccharimetry, 610-2 reactions, 690-703 mixtures, 611 partial reactivity, 691 Polygalacturonases, 671 pre treatment, 691 Polygalitol, see D-Glucitol, 1,5-anhydro reserve foods, 672-84 Polymeric compounds, methods of frac- structure, 644-59 tionation, 647 iV-acetyl, 650 Polymethylgalacturonase, 671 acids, 649 Polyols, see also Alditols, Inositols and aldehydes, 649 individual compounds, 241-98 amines, 650 action of degree of branching, 645, 650 bromine, 339 test, 643 hypohalites, 344 glycosidic linkages, acyclic, 241 anomalous, 646 cyclic, 268-98 nature, 653 Polysaccharides, 2, 562, 641-732 uniformity, 644 892 SUBJECT INDEX

heterogeneity, 655 Prussian blue, histochemistry, 633 hydroxyl groups, 648 Pseudococcus citri, 532 ketones, 649 D-Pseudoglucal, 401 methyl groups, 650 Pseudomonas species, 365 molecular size, shape, 655-9 P. putrifaciens, 521 monosaccharide units, 644 P. saccharophila, 506 identification, 602,652,713 sucrose synthesis, 521 non-reducing end groups, 650 D-Psicose, 62 sulfates, 649 Psoralen, 550 uronic acids, 648 Psoralic acid, 550 synthesis, 703-8 Pteridine compounds, 415 acid reversion, 708 Ptyalin, 678 enzymic, 703-8 Pulvinaria vitis, 532 test for branching, 643 Purdie's reagent, 370 xanthates, 694 Purines, nucleosides, 424 decomposition, 694 Puromycin, 425, 465 replacement with methyl groups, Purpurin, 552 694 Pyranose, 33 Polysiphonia species, 554 Poplar bark, 547 Pyranoside, 33 Populin, 149, 547 Pyridine, Populus species, 138, 547 catalytic hydrolysis, nucleic acids, 426 P. monilifera, enzyme system, 548 epimerization, aldonic acids, 302, 305 Poro-poro, solanum alkaloids, 546 Koenigs-Knorr synthesis, a-anomers, Porphobilinogen, 742 483 Porphyr a umbilicalis, mannan, 670 3-pyridine carboxamide, see Nicotina- Potatoes, solanum alkaloids, 546 mide starch, 91 Pyrimidines, nucleosides, 424 Primers, see under Oligosaccharides Pyrosan, 683 Primeverose, 483, 512 Pyroxylin, 692-3 ruberythric acid, 551 Pyrus leaves, blackening, 547 Primula officinalis, 512 Pyruvic acid, Pro-crocin, 542 biochemical oxidation, 777 1,3-Propanedithiol, 226 decomposition of phenylosazones, 459 2-Propanol, 1,3-dichloro, 105 Proscillaridin A, 544 Q Prosopis juliflora, 83 Protagon, 560 Quebrachitol, see L-Inositol, 1-O-methyl Proteins, combination with carbohy- Quebracho tree, 271 drates, 446-52, 709 Q-enzyme, 705 antigenic activity, 450 Quercin, see scyllo-Inositol serological behavior, 450 Quercitin, 100, 539 Proteinuria, associated glycopro teins, d-Quercitol, see mwco-Inositol, D-1- 726 deoxy Proteus vulgarisy 473, 516, 620-1 Quercitrin, 100, 539 D-Protoglucal, 401 Quer eus tinctoria Mich., 100 Prunasin, 551 d-Quinic acid, see epi-Inositol-2-car- Prunus species, boxylic acid, L-l,3-dideoxy P. armeniaca, 0-glucosidase, 588 i-Quinic acid, see epi-Inositol-2-car- P. persica, ß-glucosidase, 588 boxylic acid, D-l,3-dideoxy P. serotina, 551 Quinide, 278 SUBJECT INDEX 893

Quinoline, Rhamnus species, Koenigs-Knorr synthesis, a-anomers, R. cathartica, emulsin, 600 483 R. infectoria, 539 Quinovin, 100 Rhizopus species, 535 Quinovose, see D-Glucose, 6-deoxy Rhodeose, see D-Galactose, 6-deoxy Quinoxalines L-Rhodeose, see L-Galactose, 6-deoxy from ketose derivatives, 414 Rhodizonic acid, 279 from osones, 414 Rhodymenia palmata, xylan, 668 Rhus species, R R. semialata, 161 Racemic, R. toxicodendron L., 100 D-Ribamine, see Ribitol, 1-amino-l- compounds, 12 deoxy-D mixtures, 11 a-Ribazole, 414 Radix sarsaparillae, 546 Ribitol, 246 Raffinose, 517 1-amino-l-deoxy-D, 475 enzymic hydrolysis, 592 flavin nucleotides, 439 identification, 517 Ribodesose, see 2-Deoxy-D-eri/£/iro-pen- nutritional aspects, 796 tose occurrence, 517 Riboflavin, 266, 439, 747 preparation, 518 5-phosphate, 439 properties, 517 preparation, 423 structure, 518 D-Riboketose, see D-en/i/&ro-Pentulose Raney nickel, Ribonuclease, 637 desulfurization, 226 Ribonucleic acids, see also Deoxyribo- diglycosyldisulfides, 383 nucleic acids, Nucleic acids 1-thio sugars, 383 degradation, 177 denitration, 170 histochemistry, 635 "Raw sugar", 503 hydrolysis, Raybin reaction, 502, 525, 608 nucleosides, 425 Rayon, nucleotides, 430 acetate, 692 phosphate shift, 442 cuprammonium, 663 structure, 442 from cellulose nitrate, 694 synthesis, 177, 445 viscose, 694 D-Ribose, 84 Red spruce, 270 biosynthesis, 761 Reducing sugars, see Sugars 2-deoxy, see 2-Deoxy-D-er?/<Äro-pen- Reductic acid, 323 tose Reductone, 328 mutarotation, 51 Redwood, 270 nucleosides, 424 Refection, 783 nucleotides, 430 Reischauer and Kruis method, reducing nutritional aspects, 796 sugars, 616 occurrence, 84 Resolution, see Enantiomorphs phenylhydrazones, 80 Resorcinol test, for ketoses, 608 preparation, 84 Resurrection plant, 507 virus inhibitory activity of deriva- Reversion, 486 tives, 414 Rhamnetin, 539 D-Ribose derivatives, Rhamninose, 553 2,3-di-0-acetyl-l,5-anhydro, 222 Rhamnodiastase, 600 tetra,-0-Sicety\-aldehydot 144, 310 L-Rhamnose, see L-Mannose, 6-deoxy 3-amino-3-deoxy, 391, 465 D-Rhamnulose, see D-Fructose, 6-deoxy 2-C-(hydroxymethyl), 78, 161 894 SUBJECT INDEX

5-phosphate, 183 gosaccharides, Polysaccharides, Hexose Monophosphate Shunt and individual compounds scheme, 769 combinations with amino acids and l-a-D-ribofuranosyl-5,6-dimethyl- proteins, 446-52 benzimidazole, 414 Saccharimetry, see also Polarimetry, 5-thiomethyl, 555 Optical rotation, 611 D-Ribulose, see D-eryMro-Pentulose normal weight, 611 Rickets, effect of dietary lactose, 794 Saccharin, 66 Ring structures, see also Furanose, Saccharinic acids, 66 Pyranose, Septanose mechanism of formation, 68 general considerations, 29 preparation, glycosides, 31, 212 effect of alkali concentration, 68 polysaccharides, 646 from polysaccharides, nature of sugars, identified by glycosidic linkages, 653 bromine oxidation, 33 from starch, alkali number, 649 enzymic hydrolysis of glycosides, 34 Saccharomyces species, see also Yeasts, Hudson's rules, 34 S. bay anus, 621 Robinin, 511 D-galactose determination, 621 Robinobiose, 511 S. carlsbergensis, 621 Robinose, 553 D-galactose determination, 621 Robison ester, 182 S. cerevisiae, 620-1 Rochelle salt, 311 S. ellipsoideus, 473 "Rohferment", 575 Saccharose, see Sucrose Rosaceae, 248 Saccharum officinarum L., 502 amygdalin, 550 Sachse formulas, 40 Rosanoff convention, D-glycerose, 21 Sacrocephalus diderrichii, 274 Rubber, Borneo, 274 Safranal, 542 Ruberythric acid, 551 Safranine, reducing sugar test, 608 Rubiadin, 552 Sago palm, 0-glucosidase, 588 Rubia tinctoria, 551 Salep, Ruff degradation, for shortening carbon mannan, 670 chain, 118 mucilage, 94 2-ketoaldonic acids, 327 Salicin, 547 oligosaccharides, 482 6-benzoate, 138 Rutin, 512, 540 in vivo synthesis, 599 Rutinose, 512, 540 Saliva, 814 Rye bran, 83 Salix, 547 Rye ergot, trehalose, 507 Salmonella species, 620-1 Rye grass, fructans, 683 S. typhi, 250 Sambucus niger, 551 S sambunigrin, 551 Sapogenins, 546 Saccharase, see jS-Fructofuranosidase Saponins, Saccharate, acid, 546 complex of sucrose with metal oxide, digitalis, 545 e.g. "Barium saccharate"; see neutral, 545 under Sucrose properties Saccharic acid, see D-Glucaric acid; physical, 545 see also Aldaric acids physiological, 546 Saccharides, see also Monosaccharides, toxicity, 546 Aldoses, Ketoses, Sugars, Oli- Sarcina lutea, 620-1 SUBJECT INDEX 895

Sarcolactic acid, see L-Lactic acid Shortening carbon chain, see Carbon Sarsasaponin, 546 chain, shortening of Scabiosa succisa, 554 Sialic acid, 729 Scales method, reducing sugars, 615 blood-group polysaccharides, 721 Scammonium jalap, 99 blood-serum mucoids, 725 Scenedesmus species, Ehrlich test, "direct", 730 D-<Äreo-pentulose 5-phosphate, 761 absorption maximum, 730 Scherer test, inositols, 280, 290 interference in glucosamine analy- Schardinger dextrins, 681 sis, 475 Schiff bases, 409 isolation, 730 glycosylamines, 411 occurrence, 730 Schiff's reaction, salivary mucins, 727 aldehydo sugars, 144 structure, 731 histochemical application, 628 Silver, acetate, action on O-acylglycosyl keto sugars, 144 Schotten-Baumann reaction, 148 halides, 157 Scillabiose, 511, 544 carbonate, glycoside synthesis, 191, Scilla maritima L., 511, 544 194 Scillaren A, 544 chlorate-osmic acid reagent, 253 Scorodose, 520 cyanate, Scyllitol, see scyllo-Inositol isocyanate synthesis, 416 Scylloquercitol, see mî/o-Inositol, 2- oxide 370 deoxy alkylation, 370 Seaweeds, see Algae oxidant, 364 Secalan, 683 synthesis of glycosides, 194, 202 0-Sedoheptitol, see D-glycero-O-gluco- phosphate, mono, 175 phosphate, tri, 174 Heptitol O-acylglycosyl phosphates, 174 Sedoheptulosan, see D-aftro-Heptulose, thiocyanate, 2,7-anhydro isothiocyanates, 416 Sedoheptulose, see D-aZiro-Heptulose Silver (III) ion, glycol cleavage, 347 Sedum spectabile Bor., 102 Sinigrin, 554 Selaginella lepidophylla, 507 structure, 555 Seliwanoff test, ketoses, 608 Skin polysaccharide, 712 Semicarbazide, 452 Slimes, dextrans, 688 Seminose, see D-Mannose Snail (Helix pomatia), 88 Septanose, 146 emulsin, Sequoia sempervirens, 270 glucosaminidases, 474 Sequoyitol, see rayo-Inositol, 5-O-methyl /3-glucosidase, 589 Serratia marcescens, 620-1 aglycon specificity, 589 Serum globulins, 94 cellulase, 663 Sexual influences of certain glycosides, Snake venom, phosphodiesterase, 442 541 Sodium, Shaffer-Hartmann method, reducing acetate, acetylation catalyst, 139 sugars, *615 amalgam, reduction of lactones, 310 Shaffer-Somogyi method, reducing sug- borohydride, ars, 615 preparation of sugars, 107 Shikimic acid, 278 reduction of configuration, 288 1,2-O-isopropylidene-D-glucurono structure, 288 4,6-lactone, 136 Short carbon chain sugars, dioses, sugars, 731 trioses, 69-70 urono-7-lactones, 193 896 SUBJECT INDEX

f erropyrophosphate, Specific rotation, 51 catalytic dehydrogenation, 357 Sphingosine, 560 hydroxide, anomerization of sugar Spinach, enzymes, 183 acetates, 141 Sponges, 425 hypochlorite, oxidation of starch, 699 Spongothymidine, 425 metaperiodate, see Periodate oxida- Stabilizer of food products, tion alginic acid, 686 methoxide, Stachyose, 515, 518 formation of anhydro compounds, from verbascose, 520 378 occurrence, 519 scission of epoxides, 390 preparation, 519 naphthalenide, 371 properties, 519 perbismuthate, glycol cleavage, 215, structure, 519 218, 347 Stachys species, 519 Soja hispida, 519 S. tuberifera, 519 Solagenin, dihydro, 547 Stannic chloride, anomerization of Solanin, 546 oligosaccharides, 483 Solanum species, 546 Staphylococcus species, alkaloids, 546 S. albus, 620-1 S. demissum, 547 S. aureus, 620-1 S. sodomaeum, 547 metachromasia of capsular substance, Soldaini's method, reducing sugars, 364, 632 614 Star anise, 278 Somogyi method, Starch, 672-83 glucose, maltose, dextrine, 620 alkali number, 649 Sophora japonica, 511 amylopectin, 675 Sophorose, 511 amylose, 675 Sorbiérite, see L-Iditol amylose-amylopectin ratio, 676 Sorbinose, see L-Sorbose biosynthesis, 762 Sorbite, Sorbitol, see D-Glucitol composition, 672, 675 2-deoxy, see 2-Deoxy-D-arafo'no-hexitol phosphorus content, 672 d-Sorbose, see L-Sorbose corn, 802 D-Sorbose, enzymes affecting, 678 from D-galactose, 62 enzymic degradation, 678-83 preparation, 98 achroic point, 681 synthesis from three-carbon frag- esters, commercial, 692 ments, 114 glutinous, 676 L-Sorbose, 97 granules, 672 6-deoxy, enzymic synthesis, 759 hilum, 672 D-glucosyl-L-sorboside, 524 histochemistry, 638 phosphorylase synthesis, 525 industrial applications, 677 phenylhydrazones, 80 iodine-starch reaction, 676 disorbose dianhydrides, 225 isolation, 672 Sorbus aucuparia L., 98, 132, 248 Lintner soluble, 677 L-iditol, 251 modified, 677 Sorbus commixta Nedlund, 248 hydrolyzed, 677 Sowden-Fischer synthesis, see Nitro- oxidized, 677 methane synthesis thin-boiling, 677 Soxhlet method, reducing sugars, 615 nitrates, 169 Soybean, 0-glucosidase, 588 nutritional aspects, 781 Span 20, 40, 60, 80, surfactants, 398 effect in choline deficiency, 802 SUBJECT INDEX 897

effect of cooking, 781 &-Strophanthin-j8, 544 occurrence, 672 Strophanthobiose, 544 oxidation, fc-Strophanthoside, 544 industrial, 699 Strophanthotriose, 544 periodate, Strophanthus species, 543 Barry reaction, 701 S. kombé, 544 reaction with amines, 701 Styracitol, see D-Mannitol, 1,5-anhydro, oxidized, 698 Sucrase, see jS-Fructofuranosidase pastes, 675 Sucrose, 501-6 rétrogradation, 676 absorption, 784 swelling, 674 analogs, 524 agents, 678 synthesis, 524 thin-boiling, 698 barium saccharate, 504 waxy, 676 tricalcium saccharate, 504 Zulkowsky, 677 digestion, 784 Staudinger's equation, 657 energy of glycosidic bond, 523 Stearic acid, cerebrosides, 560 hydrolysis, enzymic, 592 Steffen process, 504 identification, 502 Steinhoff method, reducing sugars, 616 diazouracil (Raybin) test, 502 Sterculia setigera, 98 serological method, 502 Stereochemistry, 8-29 labeled, uniformly, 135 Stereoisomerism, 8 manufacture, asymmetric carbon atoms, 8 from beets (Beta vulgaris), 504 enantiomorphs, 11 from cane (Saccharum officinarum epimers, 10 L.), 502 racemic Steffen process, 504 compounds, 12 octa-O-methyl, 505 mixtures, 11 hydrolysis, 505 Sterigmatocystis nigra, 684 nutritional aspects, 784 Steroids, glucosiduronic acids, occurrence, 502 17-hydroxy, 597 phosphate, 523 enzymic hydrolysis, 597 polysaccharide formation, 706 17-keto, 597 properties, 502 enzymic hydrolysis, 597 Raybin test, 608 Straw, 85 structure, 505 Streptamine, 297 Streptidine, 558 anomeric configuration, 505 methylation method, 505 structure, 557 periodate method, 505 synthesis, 556-7 Streptobiosamine, structure, 558 synthesis, Streptococcus faecalis, 473 chemical, 485, 506 Streptomyces species, enzymic, 506, 518 S. erythreus, 465 invertase, failure, 520 S. griseus, 558 phosphorolysis reversal, 521 Streptomycin, 202, 297, 465, 558 equilibrium constant, 522 dihydro, 560 phosphate bond, point of scission, structure, 559 522 Streptomycin B, 559 Sugar, see Sucrose Streptose, 78, 202, 558 history, 5 Strophanthidin glycosides, beet (Beta vulgaris), 88, 250 biological activity, 545 pectin, 138 898 SUBJECT INDEX

raffinose, 518 T sucrose, manufacture, 504 D-Tagatose, 98 cane (Saccharum officinarum L.), 5 penta-O-acetyl, 81 sucrose, manufacture, 502 l,2:3,4-di-0-isopropylidene, 81 Sugars, see also Aminodeoxy sugars, occurrence, 98 Anhydro sugars, Deoxy sugars, preparation, 98 Aldoses, Ketoses, Saccharides, Tagua palm, 94 and individual compounds, 2 mannan, 669 branched chain, 78, 553 Takadiastase, 0-glucosidase, 588 flavor-enhancing properties, 799 trans fructosidase, 532 mixtures, separation, 602 D-Talitol, 250 qualitative detection, 602, 652, 713 DL-Talitol, 251 derivatives, 608 L-Talitol, 251 quantitative determination, 602, 652, D-Talose, 24, 53 713 mono-O-benzoyl, 149 colorimetric procedures, 616 mutarotation, 53 fermentation methods, 619 6-deoxy-3-0-methyl, 552 reducing, 4 Tampico jalap, 99 quantitative determination, 612 Tannins, 160 copper methods, 612 Tartar emetic, 311 sequestering agents, 613 Tartaric acids, see Erythraric, Threaric, unified procedures, 615 Tetraric, and individual acids ferricyanide methods, 616 Tartronic acid, see Glyceraric acid sodium borohydride method, 731 Taste, sweetness, 799 bitterness, saltiness, sourness, effect Sulfates, 170, 709 of sucrose, 96, 799 acetolysis, 170 sweetness, acid hydrolysis, 170 effect of temperature, 800 alkaline hydrolysis, 171 of sugars, 799 anhydride formation, 171 Tauber's test, pentoses and uronic histochemistry, metachromasia, 631 acids, 607 occurrence, 171 Tendomucoid, 723 preparation, 170 Tendon polysaccharide, 712 sulfur tri oxide, 170 Tetany, parathyroid deficiency, 795 Sulfonamides, Tetrahydroxymannocyclitol, 277 iV-glycosyl derivatives, 415 Tetraric acids, see also Erythraric, DL Sulfonates, see Methanesulfonates, p- and L-Threaric acids Toluenesulfonates, 163 preparation, 311 Sulfuric acid Tetrasaccharides, 513-20 acetylation catalyst, 140 Tetritols, see also Erythritol, D- and solvent, esterification, 163 L-Threitol, 242 Sulfur trioxide, sulfation, 170 Textile, size, 687 Sulfuryl chloride, 172 Thallous hydroxide, O-alkylation, 371 Surfactants, 241, 397, 560 L-Thevetose, 78 esters, 138, 163 Thiamine pyrophosphate, 747 anhydroalditols, 397 Hexose Monophosphate Shunt scheme, glycosides, 206 770 Sweet almond, /3-glucosidase, 588 Thiazoline derivatives, Sweetness value, 96, 799 cysteine with sugars, 447 Synovial fluid, 722 Thioacetals, 199, 226 metachromasia, 632 anomalous oxidation, 351 polysaccharide, 712 conversion to disulfones, 121, 360 SUBJECT INDEX 899

ketoses, 145 Thymic acid, 444 preparation, 157, 201, 226 Thymidine, 425 preparation of, Thymine, 425 acetals, 199, 228 Thyminose, see 2-Deoxy-D-en/iÄro-pen- acyclic derivatives, 226 tose deoxyalditols, 226 Thyroglobulin, 728 furanosides, 199 composition, 728 pyranosides, 199 Titanium septanoses, 146 trichloride, reduction of phenylosa- 1-thioglycosides, 199 zones, 619 Thioctic acid, see α-Lipoic acid, tetrachloride, Thiocyanate, 416 action on sugar acetates, 151 μ-thiolglycoxazolines, 417 O-acylglycosyl chlorides, 151 1-Thioglycosides, 188 anomerization, preparation, 201, 555 glycosides, 204 Thiols, 226 oligosaccharides, 483, 495 Thioses, see 1-Thiosugars Tollens test, reducing sugars, 608 Thiosorbitol, 248 p-Toluenesulfonates, 163 1-Thiosugars, 555 epoxide formation, 165 occurrence, 555 polysaccharides, estimation of pri- preparation, 199 mary hydroxyl groups, 648 reductive desulfurization, 383 preparation of new sugars, 167 Thiourea derivatives, 414 reductive cleavage, 165 DL-Threaric acid, resolution, 311 reductive hydrolysis, 165 L-Threaric acid, 311 replacement of primary with methyl hydrogen di-O-acetyl-L-threa- iodide, 164 rate, 162 nitrate, 165 1,4-L-Threitan, see L-Threitol, 1,4- replacement of secondary with anhydro ammonia, 397 D-Threitol, 242 iodide, 164, 397 DL-Threitol, 242 saponification, 165 L-Threitol, 242 synthesis of amino sugars, 470 1,4-anhydro, 384 p-Toluenesulfonic acid, 163 Ώ-threo-h-galacto-Octitol, 257, 259 aryl glycosides, preparation, 199 D-i/ireo-Pentulose, 86 (ü-xylulose) Toluidine Blue O, metachromasia, 631 5-deoxy, enzymic synthesis, 759 Tomatin, 547 a -D -glue opy r anosy 1 -D -threo -pentu - Tomatoes, 95 loside, 524 Torula species, 85 phosphorylase synthesis, 525 T. cremoris, 620-1 nutritional aspects, 795 T. utilis, 251 synthesis, enzymic, 759 mannan, 670 utilization, 86 Tosylates, see p-Toluenesulfonates L-*Äreo-Pentulose (L-xylulose), 86 Tragacanth, 685 hydrazones, 80 Tragacanthin, 685 nutritional aspects, 795 Transaldolase, 183, 755 occurrence, 86 Transfructosidase, 707 pentosuria, 86 Transglycosidation, 204 preparation, 86 hydrolytic enzymes, 531-3 utilization, 87 invertase, 531 D-Threose, 69 phosphorylases, 528-30 DL-Threose, chemical synthesis, 105 polysaccharide synthesis, 703 900 SUBJECT INDEX

Transketolase, 183, 755 U Trehala manna, 507 Trehalose, 507 Ultra-violet absorption, identification, 507 carbanilate groups, 648 nutritional aspects, 795 Ehrlich test, 730 occurrence, 507 Elson-Morgan test, 730 preparation, 507 O-triphenylmethyl groups, 648 properties, 507 Viva taeniata, photosynthesis structure, 507 absorption spectrum, 738 synthesis, 508 action spectrum, 738 Trichloroacetyl derivatives, 156 Umbilical cord polysaccharide, 712 Trifluoroacetic anhydride, Umbilicin, 243 acetylation catalyst, 140, 692 Uracil, structure, 425 cyclic phosphate preparation, 176 Urea derivatives, 414 Triphenylformazan, 617 from sugar isocyanates, 416 O-Triphenylmethyl derivatives, see also Uridine, individual compounds, 158 diphosphate glucose, sucrose synthe- ω-deoxy-co-halogeno compounds, 374 sis, 523 disaccharide synthesis, 374 diphosphoric acid, 437 hydrogen bromide, anomalous be- triphosphoric acid, 437 havior, 374 structure, 425 hydrogenolysis, 375 Urine pentose, see L-J/ireo-Pentulose hydrolysis, 368 preparation, 372 Urethans, 416 primary hydroxyl groups, estimation, Urones, see D-G1UCO- and D-Manno- 374 f uranurono-3,6-lactone polysaccharides, 648 Uronic acids, 314-25 selective triphenylmethylation, 372 aldobiuronic acids, 318 septanose synthesis, 146 aldofuranosidurono-7-lactones, 324 Triphenyltetrazolium ion, estimation of reducing action, 325 reducing sugars, 617 benzidine test, 607 Triphosphopyridine nucleotide, 745 biosynthesis, 763 Trisaccharides, 513-20 conversion to 5-ketoaldonic acids, 326 Triterpene derivatives, saponins, 546 decarboxylation, 322 Tritican, 683 derivatives, 324 Trityl, see O-Triphenylmethyl deriva- from tives aldaric acids, 315 Tuber a jalapae, 99 amides, 317 Tubercle bacilli, 94 2-furaldehyde production, 323 polysaccharides, 83 dihexuronic acids, 319 Tungstic acid, complexes, 262 identification, 318 Turanose, 508 isolation, 315 from melezitose, 516 occurrence, 314, 316 identification, 508 phloroglucinol test, 608 nutritional aspects, 795 occurrence, 508 preparation, 315, 466 preparation, 508 reactions, 322 properties, 508 reduction, 128 structure, 508 sugar interconversions, 128 relationship with maltose, 510 synthesis, 315 Tweens, surfactants, 398 Tauber's test, 607 SUBJECT INDEX 901

V Western larch gum, 88 Vaccinin, 149 Wetting agents, 560 Vaccinum species, Weygand-Löwenfeld degradation, 122 V. myrtillus L., 270 Wharton's jelly, metachromasia, 632 V. vitisidaea L., 149, 278 Wheat, Vanadium pentoxide, bran, 83 catalyst, halic acid oxidations, 345 straw, xylan, 668 Vanilla planifolia Andrews, 548 Whey, 496 Vanillin, 548 White jasmine, 519 Vegetable ivory, 94 White rots, 665 Verbascose, 519 White spruce, 94 occurrence, 520 Williamson synthesis, 370 properties, 520 Willow bark, 547 structure, 520 Wohl degradation, 119 Verbascotetraose, 520 diacetamide derivatives, 408 Verbascum thapsus, 520 mechanism, 119 Vetch seeds, 425 Wolff rearrangement, 113 Z-Viburnitol, see ra^/o-Inositol, D-1-deoxy 2-deoxyaldoses, 132 Viburnum tinus L., 276 Wolf-Zemplén degradation, Vicia angustifolia, 510 oligosaccharides, 482 Vicianose, 510 Wood, Vicine, 425 composition, 666 2-Vinyl-2,5-dihydrofuran, 396 white and brown rots, 665 Violette method, reducing sugars, 615 sugar, see D-Xylose Vitamins, X B , see Riboflavin 2 Xanthates, 159 B12 , 425 a-ribazole 3'-phosphate, 414 polysaccharides, 694 B-complex, refection, 783 reductive desulfurization, 383 C, see Ascorbic acid Xanthones, 538 Vitamin C- flavanol relationship, Xanthophyll, 740 540 occurrence, 741 K, photosynthetic phosphorylation, Xanthorhamnin, 539 757 Xanthylic acid, 432 P, 539 Xylan, 512, 666 synthesis, intestinal microflora, 802 composition, 666 effect of antibiotics, 802 crystalline, 667 effect of dietary carbohydrates, 802 degree of polymerization, 667 Vitreous humor polysaccharide, 712 hydrolysis, 667 Volemitol, see O-glycero-O-talo-lieptitol isolation, 666 Volemose, 102 occurrence, 666 Volemulose, see D-aZiro-Heptulose purification, 666 Xylitol, 245 W 1,4-anhydro, 385 dianhydro, 385 Waiden inversion, 129, 153, 165, 194 l,3-anhydro-2,4-0-methylene, 375 aluminum chloride, 482 L-Xyloascorbic acid, see Ascorbic acid hydrogen fluoride, 482 Xylobiose, 512 Wattle gum, 83 L-zî/Zo-3-Hexulose, 2-O-methyl, 328 Weerman degradation, 120, 345 L-Xyloketose, see L-iAreo-Pentulose "Wertigkeit", 572 D-Xylonic acid, 80 902 SUBJECT INDEX

cadmium, double salt with cadmium D- or L-Xylulose, see D- or L-threo-Pen- bromide, 80 tulose Ό-xylo-Pentose dialdehyde, 1,2-O-iso- propylidene, 317 Y D-Xylose, 85 Yeast, see also Saccharomyces assimilation, 85 ale, 593 cataractogenic effects, 85, 792, 796 emulsin, 563 1-labeled, 136 glycosidase system, 591 nutritional aspects, 796 adaptation, 595 cataractogenic action, 85, 792, 796 role of heredity, 595 toxicity, 796 baker's (top), 593 occurrence, 85 action on inulin, 684 phenylhydrazones, 80 brewer's (bottom), 593 preparation, 85 Yellow lupine, 519 utilization, 85 D-Xylose derivatives, Z 2-amino-2-deoxy, 471 Zeisel method, 0-methyl determination, 3,5-anhydro-l, 2-O-isopropylidene, 375 650 3,5-carbonate, 1,2-0- isopropylidene, Zinc chloride, 159 acetylation catalyst, 139 4-0-cK-D-glucopyranosyl, 527 aryl glycosides, preparation, 199 synthesis with phosphorylase, 527 Zoöglycans, see Zoöpolysaccharides oligosaccharides, 512 Zoöpolysaccharides, 709-32 4-O-ß-D-xylopyranosyl, 512 blood-group, 721 Z-Xylose, see D-Xylose hetero, 710 L-Xylose, nutritional aspects, 796 composition, 713 Xylosucrose, 530 isolation, 713