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,