Index

A value 7 Aclacinomycin 2562, 2563, 2606 ABO blood group system 1752, 1781 Acosamine 902 AB-Type 89 Actinomycetales 2550 Abzyme 380, 393 Activation step 455 Acarbose 87 Active sites 2329, 2353 Acceptor 1391 Acyclic carbohydrates 13, 14 polymer-supported 1397 anti conformations 14 Aceric acid 898 gauche conformation 14 Acetalation 121 nomenclature 14 Acetal–ketal linkage 69 OO interactions 14 Acetals 122 zig-zag conformation 13 acyclic 127 Acyclic spacers 2079 benzylidene 248 Acyl migration, O→S 1802 mixed 1305 Acyl shift, S→N 1804 open-chain 2547 Acylation 129, 1430 Acetal-type protecting group 121 N-Acylation 1431 2-Acetamido-O-acetylated glycals 708 2-O-Acyl-hex-1-enitols 706 p-Acetamidobenzyl 115 Acyloxazolidinone 914 Acetates, anomeric 664 N-Acylpyrroles, α,β-unsaturated 1065 Acetobacter xylinum 78, 1476, 1482 Addition 249, 252, 265 Acetolysis 402 Michael 254 Acetonitrile participation 1327 radical 259 Acetonitrilium ions 580, 581 exo-Addition 316 p-Acetoxybenzyl ether 115 1,2-Addition, lithiated MeSO2Ph 1982 4-Acetoxy-2,2-dimethylbutanoyl 135 1,4-Addition 1061 2-Acetoxy-3,4,6-tri-O-acetyl-D-glucal 702 radical 1040 Acetylation 130 Addition–substitution, radical 329 regioselective 131 Adenosine 1119, 1121 Acetylene-cobalt complex 777 Adenosine triphosphate (ATP) 66 Acetylenosaccharides 2096 Adenosine-diphospho-glucose (ADPGlc) 69 N-Acetylgalactosamine 1798, 2162, 2648 ADEPT 2658 N-Acetylglucosamine 1798 Adhesion domains 2357 in bacterial peptidoglycan 1542 Adjuvants 2668 polymer, in biofilms 1585 ADP-[14C]Glc 1457 N-Acetylglucosaminyltransferases 2256, 2272 ADPGlc 67, 1457 β-N-Acetylhexosaminidases 1396 Adriamycin 2562, 2565 Acetyllactosamine 1750 Advanced glycation end products (AGEs) 415, N-Acetyllactosamine 1370 1740 N-Acetylmannosamine 1861 Affinity labeling 2346 N-Acetyl-D-muramic acid (NAM) 80 AFGP, C-linked 2547 N-Acetylneuraminic acid 20, 24, 534, 596, 724, Agar 1527 772, 787, 2045 Agelagalastatin 562, 643 2-O-Acetyl-3,4,6-tri-O-benzyl-D-glucopyranosyl Agelasphines 756 bromide 708 Aglycon delivery, intramolecular 465, 595, 1303 Achmatowicz reaction 348 Agrobacterium tumefaciens 194 Acid chlorides 1463 AGU 1497 Acid-alcohol modifications 1460 AIDS 1823 Acidic degradations 383 Ajugose 70 Acidulants 854 Alanine 874, 1032 2840 I Index Alaninol 886 Allyl boronates 883 Aldaric acids 190, 1098 Allyl carbonates 138 Aldehydes Allyl ethers 116 alkynylation 1071 Allyl glycoside 159, 620 allylation 883 latent 621, 625 Alditol acetates, methylated 2209, 2211 π-Allyl palladium complex 759 Alditols 194, 202, 2432 Allylation 117, 1036, 1046 Aldohexopyranuronic acid 20 asymmetric 903 Aldol 880 Allylic alkylations 1063 Aldol condensation 867, 891 Allylic stannane 907 SnCl4-promoted intramolecular 1982, 1983 Allylic trichloroacetimidate 389 Aldol cyclization 873 2-(Allyloxy) phenyl acetyl 134 Aldol dimerizations 878 Allyloxycarbonyl group 138  Aldol reactions 871, 882, 894, 2072 2 -(Allyloxycarbonyl)benzyl (ACB) glycosides 639 Aldolase antibodies 872 P-Allylpalladium complex 1990 Aldolases 864, 2161 Allylsamarium species 1990 Aldolization, Zn-proline-catalyzed 880 Allylsilane 771, 777 Aldol-type condensations 308 Allylstannane 781 Aldonic acids 181, 194, 1095 Allyltrimethylsilane 339, 769 Aldonolactones 181, 202, 203, 210, 217, 892 Aloe polysaccharides 1529 Aldopentopyranoses 17 Alternan 75, 1199 Aldoses 843, 876 Alternansucrase 75 Aldosyl phosphates 168 Altohyrtin (spongistatin) 782 Aldosyl phosphites 168 D-Altritol 1093 Aldulosonic acids 2433 Altrosuronic acid 20 Alexine 1895 Alzheimer’s disease 414, 419, 2422 ALG (asparagine-linked glycosylation) 2268 Amadori–Heyns compounds 415 Alginates (algins) 82, 1522 Amicoratopsis trehalostatica 1964 Alkali cellulose 1520 Amide coupling 2083 Alkaline degradations 383 Amide-linked sugars 2080 Alkaloids 2619, 2624 Amido groups 1416 Alkene 682 Amination 1432 isolated 250 reductive 1748, 2123 Alkoxylation 1508 Amino acid, unnatural 1864 Alkoxymethyl ether 128 L-Amino acids, β-deuterated 1034 Alkoxyphosphonium, salt 239 α-Amino aldehyde 888 Alkyl ether 1506 α-Amino nitriles 1038 O-Alkyl glycosyl donor 569 Aminoalditols 880 Alkyl substituents 2142 2-Aminoaldonolactone 893 Alkylation 107, 1013, 1034, 1046, 1051, 1430 p-Aminobenzylether 115 1-O-Alkylation 154 Aminocyclitol antibiotic 2569 Alkyllithium 306, 1050 (1R,2S)-2-Aminocyclopentanecarboxylic acid 874 Alkylmalic acids 1033 6-Amino-6-deoxy starch 1463 Alkyne-cobalt complex 1247 D-/L-2-Amino-2-deoxy-arabinose 893 1-Alkyn-5-ols 725 Aminodeoxycarbohydrates 892 D-Allal 705, 709 4-Amino-4-deoxyfructose 881 Alligator hepatic lectin (AHL) 2457 2-Amino-2-deoxyglyceraldehyde 885 Allomorph 1481, 1482 4-Amino-4-deoxyheptono-1,4-lactam 909 (+)-D-Allonojirimycin 921 2-Amino-2-deoxypyranosyl chlorides 708 Allosamidin 1913, 1915, 1951, 1952 4-Amino-4-deoxy-threo-pentulose 881 Allosamizoline 1952, 1953, 1957, 1963, 1964, 4-Amino-4,5-dideoxy-L-lyxose 916 1972 Aminoglycoside antibiotics 1144, 2569, 2570 D-/L-Allose 876, 878, 879 Aminoglycosides 510, 2126, 2615 Index I 2841 Aminooxy 2164 Anhydrosugars 273, 284, 675, 830, 2384 α-Aminophosphonic acid ester 1039 classification 273 Aminopolyols 924 donors 684 Aminosaccharides 2427 endo-cyclic rings 284 Aminosugars 287, 816, 818, 831, 882, 888, 2574, exo-cyclic rings 284 2605, 2612 reactivity 273 preparation from sugar epoxides 286 1,2-Anhydrosugars 281, 439, 780 3-Amino-2,3,6-trideoxy pyranoses 723 1,3-Anhydrosugars 747 Amphiphatic helix 1774 1,4-Anhydrosugars 748, 784 Amphotericin 1299, 2612 1,6-Anhydrosugars 816, 830 Amygdalin 2548 1,6-Anhydrosugars, C-branched 333 α-Amylases 1195, 1451, 2093, 2331 Anhydrosugars, modified 276 β-Amylases 1452, 2621 2,5-Anhydro-5-thio-D-mannitol 2004 Amylogenin 1742 6,3-Anhydro-6-thio-octanoates 2004 Amylolyases 2340 Animal tests 2146 Amylomaize-5 73, 1441 Ankaraholide A 2558 Amylomaize-7 73, 1441 Annotation 2233 Amylopectin 73, 1426, 1440, 1450 Anomer 377 Amyloplasts 1442 Anomeric O-acylation 160 Amylose 72, 1426, 1440 Anomeric O-alkylation 455 retrograded and dehydrated 1451 Anomeric anion 791, 1356 water-soluble 1441 Anomeric center 153, 154, 180, 202, 213 Anchimeric assistance 463, 2001 Anomeric configurations 2209 Angiogenesis 2579 Anomeric conformation 2202 Angucyclines 2563, 2564 Anomeric O-deacylation 164 Anhydrides, intramolecular 272 Anomeric effect 3, 7, 8, 10, 19 Anhydro amino sugar 751 dipole dipole repulsion 8, 10 1,6-Anhydro bridge 828 exo 9 1,7-Anhydro derivatives 279 kinetic 455, 1301 Anhydro linkage 272 thermodynamic 455 Anhydro sugars, anomeric 738 Anomeric ester 525 Anhydroalditols 213, 214 Anomeric leaving group 664 1,5-Anhydro-2-deoxy-D-arabino- Anomeric oxygen 455 hex-1-enitol 700 Anomeric radicals 785, 2049, 2055 Anhydroerythritol 1101, 1121 Anomeric sulfones 2034 1,6-Anhydrofuranoses 279, 738 Anomerization 408, 430 synthesis 279 in situ 767 3,6-Anhydrofuranoses 293 Antagonist 1226 D-Anhydroglucopyranose 1476 Antarctic fish 1773 1,6-Anhydro-β-D-glucopyranose 274 Antennae 1749, 1750, 2461 1,3-Anhydroglucopyranoses 284 Anthocyanidin glycosides 2548 1,6-Anhydro-β-D-glucose 1111 Anthocyanins 2548, 2593 2,6-Anhydroheptitols 925–927 Anthracyclines 2562, 2604 1,6-Anhydrohexofuranoses 748 Anti-adhesive 2367 1,6-Anhydro-ε-D-hexopyranoses 21 Antibacterial 2430 1,6-Anhydro-D-ido-pyranose 275 Antibiotics 510, 1831, 2008, 2600 1,6-Anhydromuropeptide 742 activity 1763 2,3-Anhydro-nucleoside 289 resistances 2550 1,6-Anhydropyranoses 21, 738, 783 Antibodies 1815, 2145, 2386, 2666 boat conformation 21 Anticancer vaccines 1810 chair conformations 21 Anti-epileptic 2426 Anhydrosucrose 297 Antifreeze glycoproteins (AFGPs) 1773, 2547 derivatives 297 Antigen, F1α 551, 1821 2842 I Index Antigen presentation 2661 Ascorbic acid 186, 199, 211, 852, 985, 2631 Antigenic determinants 1752, 1755 Asialoglycoprotein receptor 1787, 2455 Antigens 2661, 2719 Aspartame 846 tumor-associated 1782, 2655 Aspergillus niger 1452 tumor-specific 2154 Asterosaponins 2559 O-Antigens 85 Asx-Turn 1778 biosynthesis 1566 Asymmetric synthesis 1029, 1031 structural diversity 1562 Atropisomerism 1763, 2575 Anti-β-hydroxy-α-aminoacids 880 Aureolic acids 2559, 2608 Anti-inflammatory drugs 1789, 1843 Australine 1895 Antimycobacterial 2407 Automated synthesis 1233 Antioxidative activity 2596 Auxiliary 1321, 1324 Antiperiplanar lone pair hypothesis (ALPH) 586 Avermectins 534, 2550, 2552, 2610 Antisense 1861 Avian virus H5N1 1947 Antithrombotic 2407 Avidity 2449 Antitumor activity 2604 Avilamycin 2554 Antiviral 996, 2407 Axes of symmetry, two-fold 2464 APC 2660 Axial attack 771 L-Apiose 837, 889 Axial bonds 64 Apoptosis 2663 Aza-Achmatowicz reaction 945 Aprosulate 2094 Aza-Cope/Mannich tandem reactions 391 APTS 1880 Aza-C-disaccharides 1154 L-Arabinal 701 1-Azafagomine 915, 916 Arabinans 1489 Azafuranose 1892 D-Arabinaric acid 1100 Azasugars 299, 366, 401, 751, 906, 1888 D-Arabinitol 87, 898 naked 930 Arabinofuranose 1575 septanose-type 299 β-Arabinofuranosylation 559 Azidation 251 stereoselective 636 p-Azido benzyl 115 Arabinogalactans 78, 498, 1425, 1530, 1536, 1572, Azido group 1339 1621, 2288 Azidoaldehydes 869 biosynthesis 1576 4-Azido-3-chlorobenzyl (ClAzb) 1256 drug target 1581 6-Azidoketones 868 larch 1530 Azidonitration 199, 253 Arabinoglucuronoxylan 1490 Azidophenyl selenylation 200, 260 D-Arabinonic acid 1098 Azidosphingosine glycosylation procedure 482  D-Arabinose 985 3 -Azidothymidine (AZT) 295, 2015 L-Arabinose 1489 Aziridine ring opening 1938 Arabinose-binding protein, bacterial 2459 meso-Aziridines Arabinosyltransferase catalytic desymmetrization (CDMA) 1950 inhibitors 1581 catalytic enantioselective ring-opening 1949 Arabinoxylans 1530 ring opening 1066 Arabitol 977, 1087 AZT 295, 2015 L-Arcanose 910 Armed donor 600 B-cells 2182, 2658, 2661, 2668 Armed/disarmed principle 453, 574, 1341 activation 2664 Aroma precursors 2621 Bacillus 1762 Aromatic spacer 2100 B. amyloliquefaciens α-amylase 1452 Aromatization 412 B. licheniformis 1452 Arugomycin 2562 B. macerans 75, 1453 Arylation 155 Bacteria 2147 Aryldiazonium salt 681 cell-surface polysaccharides 1536 1-O-Aryloxycarbonyl sugar 556 resistant 2570 Index I 2843 Bacterial cell wall biosynthesis 2575 Biofilm Bacterial engineering 1365 role in disease 1591 Bacterial expression 1366 structure 1583 Bacterial resistance 2554 Bioinformatics 2115, 2118 Bacteriophage 2366 Biolacta 1392 Bacterioprenol 2573 Biomedicine 2407 Baculovirus 1862 Bioorthogonal reactions 1850 Bamboo 78 Biopharmaceuticals 2385 Barbier conditions 1356 antibody-based 2386 Barton–McCombie reaction 214, 216 enzyme-based 2387 Base catalysis 460 glycoprofiling scheme 1874 Bayer’s patches 1567 glycoprotein-based 2387 BCB arabinofuranoside, latent 638 protein-based 2385 BCB (or ACB) glycoside, latent 640 Biorenewable materials 1439 BCG vaccine 1581 Biosurfactants 383 BCR 2664 Biosynthesis 1701, 2222 Beckmann-type rearrangement 396 Biotechnology 1381 Benzene 933 Biotin hydrazide 2176 Benzodiazepines 1018 (+)-Biotinyl-3-maleimidopropionamidyl-3,6- Benzomorphan 1043 dioxaoctanediamine (MB) 1-S-Benzoxazolyl (SBox) 2180 mannoside 1288 Birch reduction 684 Benzoyl 130 Birefringence 1445 1-O-Benzoyl sugar 545 Bislactim ether 895 Benzoylation 130 Bismuth triflate 531 2-O-Benzoyl-D-galactal 707 3,4-Bis-O-(4-nitrobenzoyl)-D-xylal 719 Benzyl carbonates 138 Bis(trialkyltin) oxide 109 Benzyl ether 108 Blase (glutamic acid specific protease) 1273 α-Benzyl GalNAc 2657 Bleomycin 2615 Benzyl glycosides 157 Blood group antibodies 1781 methoxy-substituted 158 Blood group antigens 1753 Benzylation 108 Blood groups 1752, 2280 partial 1151 A determinant 1781 selective 108 A-type 89 2-O-Benzyl-D-glyceraldehyde 884 B determinant 1782 Benzylidene 121 H determinant 1781 Benzylidene acetals, opening 108 Blue value 1449 4,6-O-Benzylidene mannopyranosyl Boat conformation 19 pentenoate 550 Boat-like transition 798 N-Benzylnitrone 888 N-Boc-7-azanorbornenone 930 Benzyloxycarbonyl group 138 Bocdene 123 2-(Benzyloxycarbonyl)benzyl (BCB) L-Boivinone 904 glycosides 633 Bond shortening 9, 10 Benzyloxymethyl ether 128 Borane 203, 205–207 Bergman cycloaromatization 2565 Bovine serum albumin 1810 Bestatin 1064 Brønsted acid 460 Bfp-OH tag (bisfluorous chain type propanoyl) α-1,6 Branch linkage 1440 1267 C-Branched sugars 306, 308, 312, 315, 324, Bicelles 40 332, 336 Bicyclic and spirocyclic compounds 1004 Branched-chain sugars 310, 816, 818, 837 Bifidobacteria 1191, 1192, 1194 Brevetoxin A 757 Bioavailability 2613, 2633 Brigl’s anhydride 280, 745 Biochemical considerations 2157 Brimacombe 291, 359 2844 I Index Bromination 250 Carbohydrate metabolism 2403 Bromine 181, 188, 192, 201 Carbohydrate microarray 1235, 2121 Bromoacetamidation, SnBr4-catalyzed 1949 Carbohydrate mimetic libraries 1236 BSA 2672 Carbohydrate mimetics 1206 maleimidoyl-conjugated 2185 Carbohydrate proteins Bulgecinine 939 N-linked 88 Bu3SnH 325, 328 O-linked 88 Butadiynyl spacer 2096 Carbohydrate recognition 2130 Butane-2,3-diacetals 121, 123 Carbohydrate recognition domain (CRD) 1785, 1,2,4-Butanetriol 386 2448 1-Butanol 1447 Carbohydrate scaffolds 1235, 2580 3-Butene-2-yl glycosides 568 Carbohydrate synthesis 2393 C-Butyl inositol 829 Carbohydrate toxins 2581 2-tert-Butyl-4-benzyl imidazolidinones 874 Carbohydrate-binding modules 2356 tert-Butyldimethylsilyl group 146 Carbohydrate-binding proteins 1780 tert-Butyldiphenylsilyl (TBDPS) group 147 Carbohydrate–metal complexes 1077 BVDU 2015 Carbohydrate–protein interactions 1235, 1381, 2121 C reactive protein (CRP) 2468 Carbohydrate–protein recognition 2101 Cadoxen 1485 Carbohydrates Caenorhabditis elegans 2249, 2258, 2272, 2275, N-linked 2386 2285 O-linked 1373, 2389 Calbistrin A 971 reducing 1127 Calcitriol 2635 Carbomycin 2551 Calicheamicins 903, 2102, 2562, 2564, 2565, Carbonates 137 2568, 2601 Carbon–carbon double bond 285 Calnexin (CNX) 1786 oxidation of 285 Calnexin-calreticulin-cycle 1786 Carbonyl compound 265 Caloric content 849 electron-releasing effect 919 Caloric intake 1439 electrophilicity 827 Calreticulin (CRT) 1786 Carbonylation 137, 165 Calyculin A 894 Carbonylative Stille cross-coupling 2069 Calystegines 1898, 1900 Carbopeptoids 996 Caminoside A 1655 Carboranes 2102  Camphanic acid 1709 2 -Carboxybenzyl (CB) glycosides 558, 568, 632  Camptothecin 1064 2 -Carboxybenzyl furanosyl donors 635 Cancer 1810, 2162, 2424, 2645, 2655, 2656, 2658, Carboxymethyl cellulose (CMC) 1506, 2666 1508, 1521 Cancer immunotargeting 2156 Carboxymethyl starch 1463 Cancer therapy 2170 Carboxymethylether 1506 ε Candida antarctica lipase B 933 N -(Carboxymethyl)lysine 417 Cannizarro 861 Cardenolide 2616 Capping 471, 1259 Cardiac glycosides 2559, 2616 Capsular polysaccharides 1536, 1582, 2700, 2701 Carrageenan 1525 biosynthesis 1586 alternatively refined 1527 in vaccines 1590 ι-type 1526 roles in bacterial virulence 1588 lambda-type 1527 Carbamate process 1496 semi-refined 1527 Carbanions 297 κ-type 1526 Carbasugars 366, 816, 836, 1913, 1982 κ-Carrageenan 1479, 1520 Carbocyclic NA inhibitors 1936, 1944 Carrier protein 2672 Carbocyclization, reductive 406 Casiraghi reaction 348 Carbohydrate genetics 2403 Castanospermine 1894 Index I 2845 Catalyst Charcoal-Celite column chromatography 92 reusable solid 447 Charcot–Leydon crystal protein (CLC) 2465 water-soluble 1058 Chased starch 1457 Catalytic domain 2352 Chemical deacylation 164 Catch-and-release 1254 Chemical functionalities 2135 Cation-dependent M6P receptor (CD-MPR) 2458 Chemical glycosylation 1388 CB arabinoside, active 638 Chemical probe 2115, 2118 CB glycoside, active 640 Chemical pulp 1499 CB glycoside method 562 Chemical shifts 26 C–C bond formation 308 Cheminformatics 997 CD52 antigen 1725 Chemoattractant 2451 + CD4 TH cells, activation 2663 Chemoenzymatic syntheses 1363, 2161 CD4+ T-helper 2661 Chemoselective coupling 574 CD8+ T-cells 1819, 2661 Chemoselective ligation 2133, 2173 Cell membranes 1699 Chemoselectivity 589 Cell surface 2135 Chewing gum 849 Cell-surface ketones 2160 Chicken hepatic lectin (CHL) 2456 Cell wall 1536, 2614 Chinese hamster ovary (CHO) cells 1772, 1861 fungal 1421 Chiral auxiliaries 1029, 1031 Cell wall constituent 498 recovery 918 Cellobiohydrolase 1 2356 Chiral environments 1029 Cellobiose 1476 Chiral ligands 1031, 1055 Cellular components 2178 Chiral scaffolds 1071 Cellular uptake 2141 Chirality-transcription strategy 1035 Cellulose 76, 1126, 1423, 1425, 1473, 1520, 2288 Chirons 887, 920 in bacterial biofilms 1585 Chitin 79, 1421, 1427, 1528, 1952, 2382 microcrystalline 1487, 1491, 1499 Chitinase-specific inhibitory activity 1952 physical properties 1486 Chitosan 80, 1528, 2382 regenerating 1496 Chloroacetates 134 Cellulose acetates 1501, 1503, 1504 Chloroacetyl (ClAc) tag 134, 1256, 1264 Cellulose content 1487 Chlorobenzene 933 Cellulose diacetate 1501 2-Chloro-3-ethylbenzoxazolium tetrafluoroborate Cellulose ester 1499, 1502 1968 long-chain 1504 2-Chloro-1-methylpyridinium iodide 1970 Cellulose ethers 1498, 1499, 1505–1507 m-Chloroperoxybenzoic acid 184, 196 Cellulose nitrates 1500 Chlorophosphates 152 Cellulose phosphate 1501 Chloroplasts 1442 Cellulose segment 77 Chlorosulfate 243 Cellulose sulfates 1500 Chlorotriazine dyes 1464 Cellulose triacetate 1503 CHO cells 1772, 1861 Cellulose whiskers 1491 Cholesterol 1616 Ceramides 1616, 1632, 1675 Choline 86 Cerebrosides 1638 Chondroitin 2286 ‘Cerný’ˇ epoxide 276, 742 Chondroitin sulfates 81, 493, 1420, 1531, 1758, Cetylhydroxyethylcelluloses 1521 1759 CFG 2130 Chromatography 1173, 1369 CGTase 75 Chromium trioxide 827 Chain elongation 882, 887 Chromium(VI) oxide 187 Chair conformations 4, 64 Chromomycin 2559 Chalcose 937 Chromophore C-1027 2568 Chalichearubinine 2568 Ciguatoxin 778 Chan rearrangement 396 Circular dichroism (CD) 42, 825, 1155 Chaperone, pharmacological 1906 Circularly polarized light 62 2846 I Index Citronellol 2623 Coupling L-Cladinose 910 dipolar 40 Claisen condensation 760 orthogonal 1333 Claisen rearrangement 390, 798, 799 SmI2-mediated reductive 1921 Clearance 1787 Coupling constants, long-range 39 β-Cleavage 2200, 2207 Coupling reaction 266, 1727 Click chemistry 2183 Covalent immobilization 2128 CMP-Neu5Ac 1373 Cp2Zr/BF3·Et2O-mediated carbohydrate CMP-sialic acid 2140 ring-contraction 1989 Codon 1864 Cross-aldol reactions 878, 905 Cohen–Tipson reaction 352 Cross-aldolizations, Mukaiyama 921 Collagens 1743 Crosslinking 1463 Collision-induced dissociation 2198 photo-activated 2183 Colominic acid 85 Cross-metathesis 475, 2056, 2057 2,8-Colominic acid, segment 83 Cross-ring cleavage 2207 Color tests 1261 (E)-Crotonaldehyde 940 Colorimetric methods 1172 Crotylstannane 907 Combinatorial chemistry 1206, 1241 Crown ethers 2097 Combinatorial synthesis 1212 Crystalline/amorphous phases 1444 Commelina communis 1904 Crystallinity 1479–1481 Compartmentalization 2473 Cuen 1485 Competitive coupling reactions 1342 Culture medium 2143 Complement-dependent cytotoxicity (CDC) Cuoxam (Schweizer’s reagent) 1485 2666 Cuprammonium hydroxide 1485, 1494 Complexity 2136 Curdlan 1528, 2128, 2381 Complex-type 1307, 1750 Curtius rearrangement 923 Compositional analysis 2223, 2224 Cyanobacteria 1605, 2558 Condensation 257 Cyanoethyl group 1715 Conduritol B tetraacetate 1931 Cyanogenic glycosides 2548 Conformational changes 2355, 2462 2-Cyanoglycals 730 Conformations 3, 1429, 1619, 2087 Cyanohydrin 315, 883 Conformers 4 Cyanosilylation 1063, 1064 Congenital disorders of glycosylation 2268  Coniferin 2598 1-Cyanovinyl (1 S)-camphanate 917 Conjugate 2706 Cyclic acetals 121, 1416 addition 902, 1049, 1051, 1065 Cyclic peptide 1005 Consensus sequence 2453 Cyclic polyene 337 Consortium for Functional Glycomics 2216 Cyclic spacers 2079 Continuous flow synthesis 1273 Cyclic sulfates 289 Convergent synthesis 604 cyclic 5,6-sulfate 297 Convolvulaceae 1900 Cyclitols 1144, 1915 Cooperativity 2577 Cyclization 321, 326, 668, 725 Copper reagents 888 dialdehydes 255 Copper-bicinchoninate reagent 1465 five-exo 1047 Core pentasaccharide 1741, 1749 intramolecular reductive 401 Core region 1608 Lewis acid-mediated aldol-like 1982 Core structures 1754, 2652 radical 324, 326, 328, 1963, 2022, 2052 Corynebacterineae 6-exo radical 325 cell wall polysaccharides 1571 SmI2-mediated radical 1986 Cosmetics 1439 Cycloaddition 238, 1021, 2182 Co-stimulatory signaling 2661 dipolar 1055, 2048 Cotton boll 78 [2+2] Cycloaddition 1046 Cotton effect 825 [2+3]-Cycloaddition 924 Index I 2847 [3+2] Cycloaddition, intramolecular 1916, 1919, Danishefsky–Kitahara’s diene 1041–1044 1982 Daunomycin 2562, 2605 Cyclodextrins 514, 1123, 2087 Daunorubicin 2562, 2568 Cycloheptane 30 Daunosamine 902, 921 boat 30 D-Daunosaminide 903 chair 30 Davis oxaziridine 1929 isoclinal 30 DCs 2668 pseudorotation 30 DC-SIGN 2458 twist boat 30 De-N-acetyl-6-sulfo-sialyl Lewis X 1338 twist chair 30 De-O-benzylation, regioselective 108, 110 Cycloheptatriene 935 Debenzylation, regioselective 1152 Cycloheptatrienone 935 Debromination, radical 833 Cyclohexane 5, 1448 Decahydroquinoline alkaloid 1041 A value 5 Decarboxylative glycosylations 557 barrier to ring inversion 5 Decin-1 2125 chair 5 Deconvolution 2124 gauche interactions 6 Decoys 2172 skew 5 Dectin-1 2128 syn-diaxial interactions 6 Deep blue color 1447 Cyclohexane-1,2-diacetals 121, 123 Degradation pathways 382 Cyclohexanone 404, 407 Degree of polymerization (d.p.) 1466, 1477 Cyclohexylidene 121 Dehydrative glycosylation 1292 2-Cyclohexyloxytetrahydropyran 34 Dehydroamino acid 1058 Cycloisomaltodextrin 76 Delignification 1487 Cyclolaminarinose 76 Deltorphin 1841, 1842 Cyclomaltodextrin 75, 1453 Dendritic cells 2660, 2692 Cyclomaltodextrin glucanyltransferase (CGTase) Dendroketose 863 1453 Denitration, radical 834 Cyclomaltoheptaose 1453 Dental benefits 848 Cyclomaltooctaose 1453 6-Deoxy-D and L-galacto-2-heptulose 868 Cyclopentadiene 932, 1037, 1053 Deoxyaldoses polyketides 879 Cyclopentane 11 Deoxyaminohexoses 943 envelope 11 5-Deoxy-D-arabinitol 897 pseudorotation 11 3-Deoxy-D-arabino-hexose 905 twist 11, 12 4-Deoxy-4-dimethylamino-D-ribonic acid 896 Cyclophelitol 1913, 1915, 1916, 1924, 1929 2-Deoxy-2-fluoro-D-glucosides 2349 (+)-/(–)-Cyclophelitol from D-xylose, 2-Deoxy-L-fucose 903 enantiodivergent synthesis 1927 1-Deoxygalactonojirimycin 899 1,2-Cyclopropanated sugars 332 (+)-1-Deoxygalactostatine 870 Cyclopropanation, intramolecular 322, 332 Deoxygenation 213, 214, 216 Cyclopropane system 398 6-Deoxy-L-glucose 901 Cyclosophorans 76 3-Deoxyglycals 718 Cycloviracin B1 1660 3-Deoxyglyceraldehyde 885 Cymarose 937 2-Deoxyglycosides 261, 626, 651 Cytidine 1119, 1121 2-Deoxyglycosyl linkages, stereoselective Cytokines 2148 construction 634 Cytosolic proteins 2168 3-Deoxy-D-hexoses 906 Cytotoxic T-lymphocytes (CTLs) 2661 1-Deoxyidonojirimycin 924 2-Deoxy-2-iodo-6-alkenyl glycoside, 6-Exo-dig DAB 1893 radical cyclization 1922 DAHP synthetase 865 2-Deoxy-2-iodogalactopyranosyl acetate 537 Daidzenin 2595 2-Deoxy-2-iodopyranosides 709 Danish agar 1527 Deoxymannonojirimycin 868, 933, 945, 996, 1889 2848 I Index

3-Deoxy-D-manno-octulosonic acid 4, 20, 21, 24, Diacetone-D-glucose 1032 1562 Diacetonomannose 279 side chain 24 3,4-Di-O-acetyl-L-rhamnal 718 6-Deoxy-L-mannose (L-rhamnose) 87 N,N-Diacetyl sialyl donor 1318, 1338 6-Deoxy-4-O-methyl-D-glucose 902 1,4-Di-O-acetyl-N-trifluoroacetyl-α,β- 1-Deoxynojirimycin 899, 924, 1889 daunosamine 713 3-Deoxy-2-oxo-L-arabinoate aldolase 866 3,4-Di-O-acetyl-D-xylal 701 3-Deoxy-2-oxo-6-P-galactonate aldolase 865 Dialdehyde starch 1462 3-Deoxy-2-oxo-D-glucarate aldolase 866 sn-2,3-Di-O-alkylglycerol 1605 3-Deoxy-2-oxo-D-pentanoate aldolase 866 Dialkylstannylene acetals 109 3-Deoxypentoses 896, 897 Dialkyltin oxide 109 Deoxypolyoxin C 921 Di-D-allosamine derivatives 1953 2-Deoxy-D-ribofuranose 87 1,3-Diaxial interactions 6, 16 3-Deoxy-D-ribohexose 905 Dibenzofurubene 1254 Deoxyribonucleic acid 87 Dibromomethyllithium 884 Deoxyribonucleotides 68 Ditertbutylsilylene 150 Deoxyribosides 2626 Dichloromalonitrile 516 Deoxysaccharides 2430 2,4-Dichloro-triazine 1463 2-Deoxy-1-seleno-furanosides 716 Dicyclohexylidene-D-glucose 1034 Deoxysugars 210, 215, 217, 219, 816, 818, 831, 2,3-Didehydro-2-deoxy-N-acetylmeuraminic acid 2550, 2551, 2562, 2564, 2574, 2616 (Neu5Ac2en) 1935 1-Deoxytalonojirimycin 933 2,3-Dideoxy-D-arabino-hexose 921     6-Deoxy-L-talose 891 2, 3 -Dideoxy-2, 3 -didehydronucleosides 350     2-Deoxythioglycosides 674 2, 3 -Dideoxy-2 ,3 -didehydrothymidine (d4T) Deoxythiohexoses 870 295, 344 Deoxythiosugars 872 2,3-Dideoxy-2,3-di-C-methyl-D-glycero-D-galacto- 5-Deoxy-L-threo-3-pentulose 896 heptose 910 2-Deoxy-3,4,6-tri-O-benzyl-D-glucopyranose 715 1,6-Dideoxy-1,6-epithio sugars 676 3-Deoxy-2-ulosonic 889 1,5-Dideoxy-1,5-imino-alditols 945 1-Deoxy-L-xylulose 873 2,5-Dideoxy-2,5-imino-allonic acid 931 Depolymerase 2366 (−)-1,5-Dideoxy-1,5-imino-D-erythro-L-allo- Depolymerization 1431 octitol 923 hydrolytic 1497 1,5-Dideoxy-1,5-imino-D-glycero-D-allo- Depolymerizing enzymes 2327 heptitol 908 Deprotection, global 1715 2,6-Dideoxy-2,6-iminoheptitol 923 Deprotonation 791 1,5-Dideoxy-1,5-iminooctitol 923 Derivatization 1497, 2199 2,3-Dideoxy-3-C-methyl-D-manno 910 Derivatizing solvents 1484, 1493 2,6-Dideoxy-3-O-methyl-D-ribo-hexose Dermatan 81, 1420, 1758, 2286 [D-cymarose] 88 Dermorphin 1841, 1842 2,6-Dideoxy-3-O-methyl-D-xylo-hexose Dess–Martin periodinane 184, 186, 191, 1923 [D-sarmentose] 88 Destomic acid 913 1,3-Dideoxynojirimycin 904, 933 Desulfation 1430 2,6-Dideoxy-D-ribo-hexaose [D-digitoxose] 88 Desymmetrization 884, 1040 2,6-Dideoxy-D-xylo-hexose [D-boivinose] 88 Dextranases 2362 Diels–Alder reaction 923, 1037, 1053, 1054, 1949 Dextrans 74, 1427, 1528, 2381 nonracemic 1929 Dextransucrase 75 Dietary fiber 1197 Dextrose 60, 845 Diethylaminosulfur trifluoride 245 DHAP 870 N,N-Diethyl-α,α-difluoro-(m- Diabetes 414, 1902, 2009, 2432 methylbenzyl)amine 246 Diacetal protecting group 123 Diethylisopropylsilylation 1917 Diacetates 885 Diethylzinc 1067 Diacetone-D-allose 1046 Digalactodiacylglycerol 1605 Index I 2849 Digitoxin 2559 C-Disaccharides 1153 Digitoxose 895, 2617 symmetrical 368 Diglycosyl disulfides 680 DISAL 568 9,10-Dihydrolysergol 2624 glycosyl donors 626 Dihydropyran 1935 Disarmed donor 600 Dihydrostreptomycin 2615 α-(2–8)-Disialic acid 1344 Dihydroxyacetone 862, 863 Disiamylborane 202, 203 Dihydroxyacetone phosphate 65, 867 Disperse Red test 1264 Dihydroxylation 197, 199, 899, 901 Dispiroketal 123 cis-1,2-Dihydroxypyrrolizidine 909 Displacement 230, 243, 258, 664, 686 Diiodosamarium 321 bimolecular 230 Diisobutylaluminum hydride 203 DAST-mediated 257 1,2:5,6-Di-O-isopropylidene-α-D-allofuranose intramolecular 244 1118 nucleophilic 229 2,3;4,5-Di-O-isopropylidene-β-D-fructopyranose sulfonate 238 1133 Disulfides 1154 Diisopropylidenegalactopyranose 186, 214 Dithioacetal 668 Diisopropylidenegalactose 204 D-Ditoxose 937 Diisopropylideneglucofuranose 190, 216 Diutan 1528 1,2:5,6-Di-O-isopropylidene-α-D- Dixanthate 262 glucofuranose 959 DMDO (dimethyldioxorane) 780 2,3:5,6-Di-O-isopropylidene-D-mannofuranosyl DMDP 1892 bromide 702 DMSO 26, 1446 Dimannosyl lipids 1606 DMTST 1326 Dimethoxymethane 9 DNA 415, 2549, 2559, 2562, 2565, 2568 Dimethylacetamide/LiCl 1486 DNA cleavage 2615 2,2-Dimethyl-1,3-dioxan-5-one 875 DNA-binding saccharides 2636 Dimethyldioxirane 196, 281, 745 Dolichols 1740, 2252, 2268, 2573 direct epoxidation 281 Donor-acceptor pairs stereoselectivity 281 matched 465 4,6-Dimethyl-2-methoxytetrahydropyran 10 mismatched 465 Dimethyl(methylthio)-sulfonium triflate 619 Donors 600, 1391 2-[Dimethyl(2- Double bond 674 naphthylmethyl)silyl]ethoxycarbonyl 142 isolated 266 Dimethylphosphinothioate 1290 Double-displacement mechanism 1784 Dimethylsulfoxide oxidation 182, 185, 190 Downstream biological process 2137 5,5-Dimethyl-1,3-thiazolidine-4-carboxylic Doxorubicin 2562, 2607 acid 874 DP, level off 1492 5,5-Dimethylthiazolidinium-4-carboxylate 874 Drosocin 1837 2,4-Dinitrophenol 2349 Drosophila melanogaster 1618, 2249, 2258, 2272, Diols 123, 885 2275, 2285 1,3-Dioxanes 122 Drug delivery 2175 1,3-Dioxan-5-one 896 Drug delivery systems (DDS) 2380, 2387 1,3-Dioxolane 122 Drug discovery 2379, 2388, 2549 Diphtheria 2710 disease-related 2388 a Diptericin 1838 DSLe 1636 Disaccharide phosphinites 1058 Dulcitol 1091 Disaccharides 32 Dynamics 36 amide-linked 2081 Dynemicin A 2568 C-linked 727, 937 nonreducing 1122 Edman degradation 1251 syn conformer 34 EGF domains 1757 torsional angles 32 EIR HPLC 1880 2850 I Index Elaiophylin 966 Epimerization 777 Electric eel acetylcholinesterase 1956 4-Epi-polyoxamic acid 909 Electrospray ionization 2194, 2195 Episelenium 1322 Electrostatic interactions 19 Episulfenium ion intermediates 1322 Elementary fibrils 1482 Epithelial cells 2647 Elimination 233, 244 Epitope 2068 SmI2-mediated 1987 Epoxidation 196, 338, 898, 899, 1035 β-Elimination 320 asymmetric 898 Elymoclavine 2624 selective 904 Empirical formula 60 Epoxide ring 2,3-En derivative 1323 migration 235 Enamine nucleophiles 864 opening 246, 252, 259, 264 L-Enantiomers 1891 Epoxides 234, 285, 961, 1709 Endo A 1809, 1828 bicyclic 828 Endo anomeric effect 9 interconversion 291 Endo H 1747 Epoxy sugars 394 Endo M 1809 2,3-Epoxy-arabino-furanoside 288 Endo-β-N-acetylglucosaminidases 1807 Equatorial bonds 64 Endo-action 2333 Ergot alkaloids 2624 Endocytosis 2665 Erlose 1180 Endodextranases 2362 ERp57 1786 Endoglycosidases 1388, 1401, 1403, 1747 Erythritol 851, 1081 Endoglycosynthases 1405 D-Erythro-L-gluco-octitol 1093 Endoinulinases 2359 meso-Erythro-manno-octitol 1093 Endoplasmic reticulum (ER) 1675, 1754, 2256, Erythromycins 961, 2551, 2611 2268 Erythropoietin (EPO) 1220, 1838, 2386 Endosomes 1677, 1683, 1685 D-Erythrose 62, 888 Endotoxic shock 1568 Erythrulose 862 Endotoxins 1569 Eschenmoser–Claisen rearrangement 799 Enediyne antibiotics 2564, 2565, 2568, 2601 Escherichia coli 561, 934, 1762, 1772, 2388 Energy contour map 1477, 1478 E-selectin 2098 Energy storage 1475 ESI-MS/MS 2205, 2209 Engineered bacteria 1380 Esperamycins 2088, 2568, 2602, 2604 Enkastines 417 Ester derivatives, formation 1462 5-Enol exo-exo-trig process 1989 Ester groups 1416 Enone 404 Esterifications 1430, 1462 Envelope 4 Esters 135, 1611 Envelope conformers 30 inorganic 1499, 1500 Environmentally benign 447 phenoxythiocarbonyl 261 Enzymatic acylation 133 Ethanol, (R)-1-arylated 1062 Enzymatic cyclization 293 Ethanol-from-cellulose 387 Enzymatic deacylation 164 Ether derivatives, formation 1463 Enzymatic degradations 2202, 2209 Ether groups 1416 Enzymatic methods 1172, 1217 Etherifications 108, 1430, 1462 Enzymatic optical resolution 1956 2-Ethoxyvinyl acetate 913 Enzymatic synthesis 691, 1219, 1269 Ethyl (R)-lactate 894 Enzyme replacement 1688 Ethyl β-D-mannopyranoside derivative 914 Enzyme replacement therapy 2387 Ethylene oxide 1463 Enzymes 1363 Ethylene spacers 2097 Enzyme-specific inhibitory activities 1992 Ethylhydroxyethylcelluloses 1521 1,6-Epi-cyclophelitol 1918, 1919, 1921, 1924 N-Ethyloxazolidinone 886 Epidermal growth factor (EGF) modules 1742 Eukaryotes 2268 C-5-Epimerase 1462 Everninomycins 2552, 2554 Index I 2851 Evernitrose 2554 Fluoro sialyl donors 1320 Evolutionary advantage 2476 Fluorogenic reactions 2185 Exo-action 2335 Fluorophore 1879 Exoanomeric effect 27 Fluoro-sugars 816 Exocellular polysaccharides 1582 Fluorous synthesis 1267 Exocyclic double bond 290 L-FMAU 2015 epoxidation of 290 Foldamers 995, 2087 Exocyclic groups 21 Folding 1908 Exo-glycals 726, 761 Food 841 Exoglycosidases 1388, 1748 Force-fields 43 Exoinulinase 2359 Formose 861 Exopolysaccharides 1416 Formyl glycals 727 bacterial 2366 Formylacetal 1266 Expressed chemical ligation 1866 Fostriecin 1064 Extracellular matrix 1758, 2146 Fourier transform ion cyclotron resonance 2198 Ezomycin A1 2579 Fragment notation 2227 Fragmentation 2224, 2230, 2237 Fabry disease 1905 in silico 2233 Factor Xa 2094 pathways 2200 FAD 67 Fragrance components 2623 Fagomine 1891 Frangomeric effect, carbonyl n electron Fast atom bombardment 2194 pairs 919 Fatty esters 1504 Friedel–Crafts arylations 772 FDA 851 Fringe 2283 FDP aldolase 865, 867 Fructans 86, 1189, 1426, 1427 Feedback inhibition 2152 Fructofuranosyl cation 377 Fermentation 182, 854 Fructo-oligosaccharides 1198 Ferricyanide/ferrocyanide/cyanide method 1464 Fructose 60, 383, 844, 846, 863, 889, 1128 Ferrier carbocyclization 404 L-Fructose into L-glucose 869 Ferrier glycosylation, intramolecular 741 D-Fructose-1,6-diphosphate aldolase 864 Ferrier rearrangement 333, 350, 354, 362, 439, Fructoside 1004 673, 716, 776, 1923, 1982, 1992 Fruits 1438 Ferrier-type glycosylation 276 Fucose 889, 892, 2164, 2275, 2386 Fibroblast growth factor 494 α-Fucosidases 1395 Fischer glycosidation 615 α-1,3-Fucosylation 2172 Fischer–Helferich method 453 O-Fucosylation 2283 Fisher chromium carbene complex 778 Fucosyltransferases 1269, 2084, 2275, 2296 FITC-avidin 2175 Functional glycomics 2115 FK-506 976 Functional mimetics 2079 Flambamycin 2552 Furan 999, 1054 Flavonoids 2592, 2631 Furaneol 384 Flavylium aglycon 2548 Furanilium ion 575 Flax 78 Furanodictine 293 Flocculate 1507 Furanoid glycals 713 Floridean starch 1426 Furanoses 3, 28, 63, 434 Fluoren-9-ylmethoxycarbonyl 142 anomeric effect 30 Fluorescence 2165, 2581 coupling constants 30 Fluorescence resonance energy transfer (FRET) pseudorotation 28–30 1777 Furanoside, branched 309 Fluoride 1288 Furanosides 1117 ion 239 Furans 412 Fluorinated tags 469 cycloadditions 917 Fluorination 245, 1261 Furcellaran 1527 2852 I Index Furfural 936 Gellan 84, 1524 α-Furyl-substituted diene 912 low-acyl 1524 Future value-added products 1176 Geminal disubstitution 7 Fürst–Plattner rule 219, 742 Gene expression 2144 Gene therapy 1688 GAG 2430 Generalized order parameter 36 α-Gal epitope 1261 Genistein 2594 Galabiose 2101 Genistenin 2595 D-Galactal 985 Gentamycin 2613, 2615 Galactans 1425, 1427, 1489 Gentio-oligosaccharides 1198 Galactaric acid 1098–1100 Geometry 2448 Galactitol 1091 Gephyrotoxin 167B 1042 Galactofuranose 1575 Geraniol 2623 Galactomannans 1426, 1427, 1519 Ginsengosides 2619 D-Galactonic acid 1097 Glass transition temperature 853, 1477, 1504 Galactonojirimycin 899 α1,4-GlcNAc 1375 Galacto-oligosaccharides (GOS) 1193 GlcNAc analogues 2167 Galactosan 739 GlcNAc 2-epimerase 2167 Galactose 877, 1130 O-GlcNAc protein modification 2133 Galactose oxidase 186, 1774 O-GlcNAc transferase 1758 α-Galactosidase 2209, 2387 GlcNAc transferase V 2390 β-Galactosidases 1193, 1390, 2013 GlcNAc-1-phosphotransferase 2271 Galactosyl phenylcarbonate 551 GlcNAc6ST 1377 Galactosylceramides 488, 1676 GlcNAcT-IVa 2205 Galactosyltransferases 1269, 1783, 2084, 2259, GlcNLev 2174 2278 Globo H 1782, 1811, 2389 Galacturonans 1425 Globo-series 1373 Galectins 1786 Globotriose 2101 Galili epitope 2281 Glucal 337, 700 Gallotannins 2600 stannylated 2069 GalNAc analogues 2163 α-1,4 Glucan lyase 381 Ganglioside catabolism 1683 β-Glucanases 2354 Ganglioside GD3 1344, 1346 Glucans 498, 1425–1427, 1489 Ganglioside GM3 1323, 1333 Glucansucrases 70 Ganglioside GQ1b 1328 Glucaric acid 190, 1098–1100 Ganglioside HLG-2 1352 Glucitol 86, 905, 1092, 1457 Ganglioside synthases 1678, 1680 Glucoamylase 1452, 1465 Gangliosides 1230, 1373, 1616, 1634, 2433 Glucocerebrosidase 2387 Gangliosidis 1672 Glucomannans 1425–1427, 1489, 1490 Gangliosidosis 1683 D-Gluconic acid 1095 GM1 1685 Gluconobacter sp. 194 GM2 1686 Gluco-oligosaccharides 1198 type 1 1685 Glucopyranose 64, 997 Gastrointestinal tract 1188 2-O-α-Glucopyranosyl-L-ascorbic acid 2631 Gaucher disease 1906 D-Glucoronate 1135 Gb3 oligosaccharide 1267 Glucosamine 853, 1068, 1704, 1959, 1961, 1964, GC-MS 2203 2082, 2429 GDP-fucose 1273, 2165 Glucosaminoglycans 1148 Gel 1428 Glucose 60, 843, 1129, 1130 Gel formation 1475 D-Glucose 64, 68, 876, 878, 1128 Gel permeation chromatography 2454 L-Glucose 910 Gel state 1619, 1620 Glucose homopolymer (GHP) ladder, 2-AB labeled Gelatinization temperature 1445 1881 Index I 2853 Glucose oxidase 182, 1466 Glycerol kinase 868 Glucose sensor 2423 D-Glycero-D-manno-heptitol 1094 Glucose transporter 2424 L-Glycero-D-manno-heptose 1562 Glucosidase inhibitors 1902, 1916 Glyceropeptidolipids 1607 Glucosidases 1920, 2269, 2349 Glycoaldehyde 891 Glucosuria 2011 Glycoamidases, inhibitor 1849 Glucosyl isopropenylcarbonate 552 Glycoblotting 2117 Glucosyl 4-pentenoates 549 Glycocalyx 1775, 2581 Glucosyl–uronic acid–methyl amine 2085 Glycoclusters 2092 Glucosylceramide 1676 Glycoconjugates 452, 1365, 1720, 1727, 1729, D-Glucuronic acid 2095 2700, 2715 Glucuronidated 510 functionalized 2550 Glucuronoarabinoxylans 1425 multivalent 2550, 2581 Glucuronoxylomannans 1427 Glycodendrimers 2097, 2581 O-Glucuronylation 527 Glycodiversification 2638 Glycal assembly method 747 Glycodrug discovery 2379, 2393 Glycal epoxide 780 Glycoengineering 2385, 2386 Glycals 184, 191, 196, 197, 199, 200, 218, 237, Glycoform profile 1876 249, 250, 252, 275, 318, 322, 330, 332, 439, Glycoforms 1737, 1776 673, 741, 776, 911, 1297 Glycofragment mass fingerprinting 2236 branched 711 Glycogen 74, 1422 3-C-branched 720 Glycogen phosphorylase inhibitors 1903 C-2-acylated 727 Glycogene library 1380 donors 685 Glycogenin 1743 intramolecular glycosylation 275 Glycoglycerolipids 533, 1622 Glycan array technology 1381 Glycoinformatics 2238 Glycan charge profiles 1880 Glycolaldehyde 862 Glycan hydrolases 2350 Glycolipids 605, 756, 1224, 1362, 1603, 1604, GlycanBuilder 2231 1629, 1697, 1699, 2121, 2203, 2284 Glycans 1416 phenolic 1607 high mannose-type N-linked 1827 plant 1611 N-linked 1874 polyisoprenoid 1618 O-linked 1874 synthesis 1373 release 1878 Glycolyl groups 2142 sequencing, de novo 2226 Glycomes 2115, 2192, 2193, 2203, 2221 structures, editor 2231 Glycomics 1364, 2115, 2116, 2137, 2191–2193, sulfated 1377 2221 N-Glycans 1212, 1214, 1251, 1738, 1749, 2203, Glycomimetics 997 2209, 2246, 2248, 2255, 2268 Glyco-peakfinder 2228, 2229 O-Glycans 1373, 1753, 2203, 2246, 2249, 2258, Glycopeptide amino acid 2173 2281 Glycopeptide antibiotics 1554, 1762, 2574 O-glycans hydrophobic derivatives 1557 mucin-type 1754 Glycopeptide antibiotics, cyclic 1832 Glycemic index 849 Glycopeptide mimetics 1849, 2671 Glyceraldehyde 61, 62, 863, 883 Glycopeptide vaccines 2671 D-Glyceraldehyde-3-phosphate 65 Glycopeptides 1219, 1221, 1224, 1727, 1883, D-Glyceric acid 62 2097, 2211, 2671 D-Glycero-D-galacto-heptitol 1093 C-linked 1849 Glyceroglycolipids 1642 N-linked 1800 meso-Glycero-gulo-heptitol 1094 O-Glycopeptides 531, 1800 D-Glycero-L-gulo-heptitol 1094 Glycopeptidolipid 608 meso-Glycero-ido-heptitol 1093 Glycophosphopeptide 1848 Glycerol 86 Glycopolymer 2384 2854 I Index Glycoprofiling 1873, 1884 neutral 1616 P-Glycoprotein 2607 synthesis 482 Glycoprotein sequence, mapping 2214 Glycosphingosines 1639 Glycoproteinoses 1685 Glycosyl acceptor 453, 458 Glycoproteins 1219, 1362, 1365, 1701, 1729, Glycosyl acetates 525, 526 1737, 1860, 2097, 2121, 2138, 2645 Glycosyl amine 1800 asn-linked 1281 Glycosyl amino acids 586, 1799 folding 1777 C-Glycosyl amino acids 790 homogeneous 1797 N-Glycosyl amino acids 488 S-layer 2251 O-Glycosyl amino acids 488 production 2388 Glycosyl azides 747 synthesis 488, 2387 Glycosyl bromides 429, 580 therapeutics 1873 Glycosyl carbamates 2092 O-Glycoproteins 1742, 1743 Glycosyl carbanion 704 O-Glycoproteins, mucin-type 1753, 1756 Glycosyl carbonates 551 Glycoproteomics 2115, 2211, 2214 Glycosyl chloride 429 Glycopyranosyl iodide 2043 C-Glycosyl compounds 2022 Glycorandomization 2393, 2638 Glycosyl couplings, β-stereoselective 636 Glycorecognition 2447 Glycosyl diacylglycerols 1611 Glycosamino acid(s) 996 Glycosyl donors 429, 453, 526, 663, 746, 751, Glycosaminoglycans 81, 493, 1217, 1418, 1421, 1717, 1799 1427, 1758, 1759, 2246, 2286 generation 453 N-Glycosidase 2473 unprotected MOP 645 Glycosidase inhibitors 663, 1888, 1913, Glycosyl fluorides 429, 580, 588, 626, 643, 747, 1915, 2082 834, 1399, 1705 natural 1992 Glycosyl halides 213, 214, 429, 785 Glycosidases 299, 1364, 1388, 1782, 1783, 2139, Glycosyl hydrolysis 2338 2245, 2259, 2267 Glycosyl imidazole groups 19 inhibitors of 299 Glycosyl iodide 429 inverting 1784 Glycosyl lithium 2022 mutant 1403 O-Glycosyl N-methyl-acetimidates 458 retaining 1784 Glycosyl mimetics 2090 α-Glycoside 440, 1316 Glycosyl pentenoate 1294 β-Glycoside 440 Glycosyl phosphates 167, 282, 1,2-cis-α-Glycoside 530 580, 626, 1254 Glycoside bond 452 C-Glycosyl phosphonates 368 Glycoside hydrolases 379, 2342, 2350 Glycosyl pseudothiouronium salts 677 O-toC-Glycoside rearrangement 772 Glycosyl 2-pyridinecarboxylate 547 Glycosides 843, 1113, 2591 Glycosyl 2-pyridyl thiocarbonate 554 2-C-branched 322 Glycosyl radicals 704, 2022 intramolecular 274 Glycosyl samarium 2022, 2038 N-linked 1797 Glycosyl sulfonate 1282 O-linked 1797 Glycosyl sulfonylcarbamates 552 C-Glycosides 27, 282, 356, 362, 366, 514, 747 Glycosyl sulfoxides 663, 1289 acetylenic 282 Glycosyl thioacetates 677 aryl 282 Glycosyl thiocyanates 678 preparation of 356 Glycosyl thioimidocarbonates 680 N-Glycosides 1740 Glycosyl transferases 299, 1782 O-Glycosides 440, 1742 N-Glycosyl triazole derivatives 439 Glycosidic linkage 1362, 2547 α-Glycosyl triflate 1289 Glycosphingolipids 643, 1611, 1616, 1618, 1672, Glycosyl xanthates 679 2248, 2284 Glycosyl ylide 792 acidic 1616 Glycosylamines 1036 Index I 2855 Glycosylation 429, 460, 1316, 1705, 1720, 2222 Gram-negative bacteria 1559, 1761 base-promoted 686 outer membrane 1559, 1562 double differential 599 Gram-positive bacteria 1761, 1763 enzymatic 1388, 2388 Gram-scales 1370 intramolecular 556, 628 Granule, water-insoluble 1450 N-linked 1798 Granules 1442 O-linked 1798 Green plants 1438 machinery 2138 Grignard reaction 767, 1045 pathways 2133 Grignard reagent-derived cuprates 1049 random 1207 Growth rings 1444 semiorthogonal 1711 Grubbs’ catalysts 1720, 1924, 1982 site profiling 1883 GS-4071 1935 stereocontrolled 602 GS-4104 1935, 1944 C-Glycosylation 595 GSL-enriched microdomains (GEMs) 1673 intermolecular 789 GT3 1328 radical 789 Guanidine-linked sugars 2090 N-Glycosylation 2214, 2255 4-Guanidino-Neu5Ac2en 1935 β-Glycosylation, O-alkylative 1301 Guanosine 1119, 1121 Glycosylation analysis, quantitative 1883 Guar gum 1519, 1528 Glycosylation pathways, inhibition 2170 D-Gulal 705 O-Glycosylation sites 2211 D-Gulonic acid 1098 N-Glycosylation sites, conformation 1779 α-L-Gulopyranosyl uronic acid 83 Glycosylation step 455 Gulose 877 Glycosylhydrolases 1388, 1807 Gum acacia 1524 Glycosylidene 761 Gum arabic 83, 1524 Glycosylidene acetals 1303 Gum ghatti 84 Glycosylmethyl-triazenes 2348 Gum sources 1515 Glycosylphosphatidylinositol (GPI) 475, 505, 605, Gum tragacanth 84 1254, 1650, 1697, 1699, 1738, 2248, 2285, Gums 1428, 1513 2582 natural 1491 Glycosylthiolate anion 1354 Gun cotton 1500 Glycosyltransferases 1217, 1364, 1673, 1807, 1833, 2139, 2245, 2255, 2267, 2289, 2298, Haemocyanin, keyhole limpet 1810 2388, 2393 Haemophilus ducreyi 2161 immobilized 1378, 1380 Haemophilus influenzae type B (Hib) 2391, 2700 inverting 2299 N,O-Halfacetals 515 retaining 2303, 2305 O,O-Halfacetals 515 Glycosynthases 691, 1388, 1403, 1785 S,O-Halfacetals 515 Glycotides 2082 Half-chair 5 GlycoWorkbench 2230–2232, 2235 Halichondrin B 983 Glycuronopyranosylamine 2082 Halide-assisted conditions 667 Glycyrrhetic acid glycoside 540 Halides 263 Glycyrrhizin 2621 source 239 Glyoxalase inhibitor 1982 α-Halo carboxylic acid, β-branched 1040 GM4 1676 1-O-Haloacetyl glucoses 544 Gold glyconanoparticles 2581 Halobacteriaceae 1605 Golgi apparatus 1675, 1754, 1861, 2254, 2256, p-Halobenzyl ethers 116 2271 Halogen, source 246 Golgi localization 2158 Halogen sugars 666 gp120 1827 Halogenation 238, 241 gp41 1827 limitations 241 GPI 1650, 1699, 1729, 1744 other combinations of reagents 241 GPI anchors, biosynthesis 1745 Halohydrin 575 2856 I Index Halonium ion transfer 576 Hex-5-enopyranosides 196, 211 Halosulfonamidation 253 Hexenyl glycosides 575 Hard Sphere Exo-Anomeric 42 Hexopyranoside-derived template 1049 Hassel–Ottar effect 13 Hexosamines 2427 HDA (hetero Diels–Alder) 335, 347, 910 Hexosaminidases 2277 Heart transplants 2409 Hexose enzymes, structural investigations 2413 Heavy metal salts 430 Hexoses 63, 68, 864, 898, 913, 2409 Heck coupling reaction 1045 biomedicine 2421 Helferich modification 1318 O-hetarylation 645 Helicobacter pylori 1830 metabolism 2418 Helix 1479 Hfb-OH tag (hexakisfluorous chain type butanoyl) left-handed 2087 1267 right-handed 2087 High performance liquid chromatography Hemagglutination 2465 (HPLC) 92 Hemagglutinin 1863, 1933, 1935, 2390 High-acyl gellan 1524 Hemato-encephalitic barrier 2591 High-amylose 1426 Hemato-intestinal barrier 2592 Higher sugars 197, 291, 359–361 Hematological disorders 2162 Brimacombe synthesis 359 Hemiacetal 63, 764 Jarosz synthesis 360 Hemicelluloses 68, 76, 78, 1424, 1473, 1488, 1530, Secrist synthesis 359 2289 synthesis 291 Hemoglobin-AIc 414 Highly branched component 1441 Heparan sulfate 82, 494, 1217, 1420, 1758, 1759, High-mannose glycan 1214 2096, 2286 High-throughput analysis/synthesis 1233, 1241, Heparan sulfate proteoglycans 2383 2130 Heparin 494, 1217, 1264, 1421, 1758, 1759, 2094, Hikizimycin 899, 900 2383 Hikosamine 899, 900 oligosaccharides 2126 HILIC 1881 Heparin sulfate 82 Histone acetylation 2144 Heparinoid mimetics 2100 Histone deacetylase inhibitors 2144 Hepatic glucose production 1903 HIV 1823, 2126 Heptahydroxypentadecanals 927, 929 antigen, glycopeptide 1823 Heptitols 1093 envelope proteins 1825 Heptonic acids 2081 infection 2085 Heptoses 1401 influenza 2154 biomedicine 2427 protease inhibitor 1064 Herbal medicines 1904 vaccine 1825 Herbicides 2009 Holocellulose 1491 Herbimycins 969 Holothuroids 2559 Hesperetin 2598 Homo-aza-sugars 2088 O-Hetaryl glycosides 644 HomoDMDP 1893 O-Heteroaryl glycosyl donor 644 Homogalacturonans 2289 Heteroatoms 229 Homoglycans 498 Heterocycles 512 Homologation 886 Hetero-Diels–Alder additions 347, 910, 913, 2067 α-Homonojirimycin 1891 asymmetric version of 348 Homopolysaccharide 1488 high pressure conditions 348 L-Homoproline 870 Lewis acid catalysis 348 Honey oligosaccharides 1179 Hetero-Diels–Alder adducts 911 Hopanoids 1621 Heterogeneous catalysts 181, 202, 206, 444 Horner–Emmons 889 Heteroglycans 498 Hp-s6 ganglioside 1347 Heteropolysaccharides 1473, 1488, 1490 HPAE-FD 1880 Hex-2-enopyranosides 210, 722 HPAE-PAD 1880 Index I 2857 Hsung–Vedejs AD-mix 942 coupling constants 26 Huisgen cycloaddition 1833, 1850, 2183 differentiation of the reactivity 284 Human β chorionic gonadotropin (β-HCG) 1777 dimethyl sulfoxide 25 Human blood group determinants 71 hydrogen bonding 26 Hyacinthacine 1896 hydrogen bonds 27 Hyaluronan 1758, 1759, 2096 non-anomeric 153 Hyaluronate 1419, 1421 water 26 Hyaluronic acid 81, 494, 1419, 1421, 1531, 1758, Hydroxymethyl groups 14, 16, 22 1759, 2383 gauche effect 22 Hybrid type 1750 hydrogen bonding 22 HYCRON 1812 solvent effects 22 Hydantocidin 2579 5-Hydroxymethylfuraldehyde (HMF) 381, 412 Hydrazide 2164 4-Hydroxy-4-methyl-2-oxoglutarate aldolase 866 Hydrazinolysis 1747, 1878 4-Hydroxymethyl-2-pentulose 862 Hydride-reduction 1062 ε-Hydroxynorleucine 2675 Hydroboration 763 4-Hydroxy-2-oxo-glutarate aldolase 866 Hydrocolloids 1491, 1507, 1513, 1516 2-Hydroxypropanols 886 Hydrocyanation 1056 Hydroxypropyl cellulose (HPC) 1506, 1509, 1521 asymmetric 1056 Hydroxypropylmethylcelluloses (HPMC) 1521 Hydroformylation 317, 1060 3-Hydroxytetrahydrofuran 13 Hydrogen bonds 22, 25, 1444, 1450, 2575, 2576 Hygromycin B 2554 Hydrogenation 210, 211, 1057, 1061, 1067, 1068 Hyperglycemia 2011 Hydrogenolysis 108, 1725 Hypermannosylation 2249 Hydrolases 2335 Hypochlorite 1462 inhibitors 2346 HYTRA 894 Hydrolysis 377, 1517 reverse 1388 Ibuprofen 1059 Hydrophilicity 2591 IBX 254 Hydrophobic bonds 1264, 1444 L-Iditol 1093 Hydrophobic interactions 2575, 2576 Idopyranose 16 Hydrophobic tag 1210, 1269 chair conformers 17 Hydrophobically assisted switching synthesis Idose 877 (HASP) 1269 Iduronic acid 2095 Hydrosilylation 1062 skew conformation 20 Hydrothermal degradation 381 L-Iduronic acid 16, 202, 596, 1462 Hydrovinylation 1058 IgG 2386 asymmetric 1056 Ig-superfamily 2475 Hydroxy ethers 1463 2-Imidate sialyl donors 1333 Hydroxyacetic acid 2099 Imidate synthesis 456 Hydroxyalkylether 1506 Imide halides 516 Hydroxyalkylmethylcellulose 1508 Iminium, salt 242 Hydroxybutyrate aldolase 866 Iminoalditols 869, 870, 872, 942 3-Hydroxy-γ -butyrolactone 385 1,5-Imino-L-fucitol 889 2-(Hydroxycarbonyl)benzyl (HCB) mannoside 1,5-Imino-D-glucitol 870 1293 1,5-Iminohexitols 870 Hydroxyethylcelluloses (HEC) 1506, 1508, 1509, 1,4-Imino-D-lyxitol 893 1521 Imino-D-mannitol 870 Hydroxyethylmethylcelluloses (HEMC) 1506, Iminophosphorane 1804 1521 Iminosugars 996, 1888 α-Hydroxyfurans 399 C-branched 312 2-Hydroxyglucals 673 2,5-Imino-2,5,6-trideoxy-D-altritol 915 Hydroxyl groups 3, 284 IMM micromixer 1274 chemical shifts 26, 27 Immobilization, noncovalent 2122 2858 I Index Immune evasion 2666 Isomerization 351 Immune system, innate 1224 of epoxides into allylic alcohols 351 Immunological memory 2663 Isopropenyl glycosides 568, 616 Immunotherapy 2176 armed 618 Indium 318 disarmed 618 Indium-mediated addition reaction 1929 Isopropylidene 121 Indolizidines 922, 1893 Isopropylidene acetal 1303 Infection 2391 1,2-O-Isopropylidene-α-D-glucofuranose 1118, Inflammatory cascade 1788 1133 Influenza 1933, 2130, 2390, 2582 2,3-O-Isopropylidene-D-glyceraldehyde 908, 921 Influenza A (H1N1) 1941 2,3-O-Isopropylidene-α-L-sorbofuranose 1133 Infrared spectroscopy 825 Isostere 2453 Inhibitors 311, 996, 1011, 1229, 2345, 2349 Isotactic 1476 mechanism-based 2347 Isoxazoline 1917 Inosine 1119, 1121 Ivermectin 2610 Inositol 1108, 1704 myo-inositol in mycobacterial cell wall 1578 Jelly-roll motif 2464 cis-Inositol 1110 Julia coupling 763 epi-Inositol 1110 Junction zones 1517, 1522, 1523 myo-Inositol 1108 K252a 2549 Inositolphosphoglycan 510 Kanosamine 899, 900 Insect cell 2388 Karplus equation 39 Insects 2147 Katsuki–Sharpless epoxidation 898, 937, 938 Insulin 1863 KDN 796, 1315 Insulin-like growth factor 1742, 2097 KDO 4, 20, 21, 796, 864, 866, 908, 912, 1838 Integrins 996, 2579 bacterial lipopolysaccharide 1562, 1564 Inteins 1805 side chains 24 Interoperability 2238 KDO aldolase 865 Intramolecular SN2-type reaction 1301 KDO α-methyl glycoside 912 Inulin 86, 1189, 1191, 1192, 1201, 1426, 1529, KDO synthetase 865 2358, 2359 Kedarcidin 2568 Inverse procedure 463 α-L-Kedarosaminide 904 Invert sugar 844 Keratan sulfate 82, 1420, 1758, 1760, 2286 Inverted non-bilayer phases 1622 Kestose 1178 Iodine/iodide colors 1447, 1464 Ketene imines 516 Iodocyclizations 255 3-Ketofuranose 316 1-Iodo-D-glucal 730 Keto2Gal 2174 Iodolactonization 336, 894 Ketoimines 1063 Iodopyranose derivatives 1986 Ketone groups 2142 Ion-dip infrared spectroscopy 25 Ketone sugar 314 Ionic liquids 447, 463 Ketones 60 Ionization technique 2195 Ketose 843 Ipomoea carnea 1900 Ketosulfoxides 889 Ireland–Claisen rearrangement 799 Ketouridine 321 Isoamylase 1453, 1455 Kiliani–Fischer 258 Isoflavonoids 2595 Kinetic resolution 937 L-Isolecucine 874 Kishi’s rule 199 Isolevoglucosenone 940, 2069 Klebsiella 2366 Isomaltase 1981, 2090 KLH 1813, 2672 Isomalto-oligosaccharides 1195, 2360 Knoevenagel condensation 758 Isomaltose 2090 Koenigs–Knorr method 430, 453, 615, 667, 1013, C-Isomaltoside 2026 1318 Isomaltulose 1175 Konjac glucomannan 1530 Index I 2859 Kraft or sulfate pulp 1488 Levulose 60, 847 KRN7000 756 Lewis acid–Lewis base bifunctional system 1063 K-Selectride 888 Lewis acids 430, 460, 665, 1050 KSGal6ST 1377 tin-based 542 Lewis antigens 2655 Labeling 1879 Lewis blood group 90, 1782, 1821, 2013, 2014, Lactacystin 972 2066, 2084, 2104, 2165, 2450 β-Lactamases 2008 oligosaccharides 1254 β-Lactams 1557 Lewis epitopes 1258, 2280 Lactic acid 863 Library 1206, 1225, 1241, 2237 Lactol 757 prospecting 995 Lactone 308, 309, 321, 328, 335, 338 Library-based sequencing 2225 Lactose 69, 71, 1193 Ligands 1029 Lactosucrose 1181 Ligation Lactosylceramide 1676 native chemical 1801, 1866, 2388 LAM 1651 sugar-assisted 1803 Laminin 2465 Lignans 2599 Landomycin A 537, 2564 Lignins 1491, 2598 Larch gum 1530 Limit dextrin 1452 Large-scale synthesis 1366 Limulin, horseshoe crab 2469 Lasalocid A (X537A) 799 Linalool 2623 (–)-Lasiol 1051 Lincosamine 913 Lawesson’s reagent 680 Linkage analysis 2203 Laxation 849 Linkers 472, 1243, 2079 threshold 851 Lintner procedure 1460 LC, online nano- 2214 Lintner soluble starch 73 LC/MS 1882 Lipases 133, 884, 1301 LDA 1355 LIPDAT 1623 Leaves 1438 Lipid A 1224, 1564, 1608, 1619, 2392 Lectins 1785, 2145, 2390, 2463 structure 1560 C-type 1785, 2448 synthetic derivatives 1567 galactose-specific 2104 LipidIandII β-galactoside binding 2466 peptidoglycan precursors 1545 I-type 1786 Lipid rafts 1673 mannose-binding 2041 Lipid, unsaturated 1721 P-type 1786 Lipoarabinomannan 502, 1536, 1607, 1621 Legume 2447, 2596 as a drug target 1581 Leishmaniasis 1831, 2581 biosynthesis 1577 Leloir pathway 1783 mycobacterial cell wall 1574 Leloir transferases 1783 Lipoglycodepsipeptide 1837 Lemieux–Morgan conditions 615 Lipomannan 1577, 1607, 1621 Lentinan 2381 Lipooligosaccharides Lepicidin A 540 bacterial 2138 Leucomycin 2551 trehalose-containing 1607 Leuconostoc mesenteroides 74 Lipooligosaccharides (LOS) 1562, 2392 Leucrose 1181 Lipopolysaccharides 1536, 1608, 2700 Leukocyte adhesion deficiency 2452 antibacterial vaccines 1570 Leukocyte trafficking 1788 biosynthesis 1564 Levan 86, 1191 E. coli 561 Levoglucosan 738, 959, 1017, 1111, 1130 in cancer treatment 1570 Levoglucosenone 749, 940, 973 neutralization 1569 Levulinoyl 136 structure 1560 Levulinoyl ester 136, 1254 Lipoteichoic acid 1643 2860 I Index Liquefying enzymes 1451 Maltotetraose 1451, 1453 Liquid-crystalline state 1479, 1505, 1619, 1620 Maltotriose 1451 Lithiation, reductive 299 Mammalian cells 1860, 2146 of epoxides 299 Manganese(IV) oxide 191 of oxiranes 299 ManLAM 1581 Lithio glycal 792 ManNAc 2152, 2157 Lithiomethyl sugars 2031 analogues, synthesized thiol-derivatized 2179 Lithium acetylide 783 Mannans 78, 498, 1425–1427 Lithium aluminum hydride 203, 204, 206, 214, 219 D-Mannaric acid 1100 Lithium diphenylphosphine 264 Mannich reactions 880–882, 1052 Lithium reagents, anomeric 2038 Mannich–Michael reaction 1042 Locked nucleic acids (LNA) 295 Mannitol 87, 851, 990, 1022, 1089 Locoism 1894 ManNLev 2156 Locust bean (carob) gum 1428, 1519 β-Manno-glycoside 1280 Long-chain carbohydrates 921, 922 D-Manno-hept-2-ulose 889 Long-range participation 1324 L-Mannonic acid 1097 LPS 1226, 1570, 1619 L-Mannonic-γ -lactone 983 LTA 1620, 1621, 1643 Mannonojirimycin 905 LUDI 2104 Mannopeptimycins 1833 Lung cancer 2600 β-Mannopyranoside synthesis 465 Lutropin (LH) 2457 β-Mannopyranosylation 550, 558 Lyases 2260, 2327, 2339 stereoselective 633 Lymphocyte homing 2174 D-Mannosamine 888 Lymphocyte trafficking 2164 Mannosan 739 Lyocell 1487, 1494, 1495 Mannose 876, 878, 1128, 1132, 2547 Lysosomal disease 2387 C-linked 2546 Lysosomal hydrolase 1683 Lysosomal sialidase 1683 Mannose-containing oligosaccharides 2126 Lysosomal storage disorders 1684, 1905, 2462 Mannose-6-phosphate 1846 Lysosomes 1683, 1685, 1788, 2259, 2271 Mannose-6-phosphoric acid 2387 Lysozyme 2338, 2592 Mannosidases 1308, 1396, 1399, 1405, 2256, 2269 D-Lyxitol 894, 898 inhibitor 2596 α D-Lyxonic acid 1098 -Mannosidases, inhibitors 932 β Lyxose 876, 1127, 1128, 1130–1132 -Mannosides 204–206, 635 Mannostatine 1951 Macrolides 1022 Mannosyl bromide 1285 antibiotics 2551, 2611 Mannosyl chloride 1283 β Macrophage mannose receptors 2416 -Mannosyl linkage 1214 Macrophages 2387 Mannosyl transferase 1309 β Maillard reaction 846 -Mannosylation 1405 Maize 1426 C-Mannosylation 1746, 2546 Malaprade oxidation 889 O-Mannosylation 2284 Malaria 1830, 2582 Mannosyl-N-phenyltrifluoroacetimidate 1293 Malaria toxin 2583 Mannosyltransferases 2256 MALDI-MS 1882, 2194, 2195, 2209 in mycobacteria 1578 MALDI-TOF MS 93, 94 using decaprenyl phosphate donor 1578 Malonyl radicals 330 C-Mannosyltryptophan 783 Malt α-amylase, barley 1452 α-Manno-type analogue 1919, 1921 Maltase 1981 Marcellomycin 2606 Maltohexaose 1453 Mass analyzers 2196 α-Maltohexaose-(1→4)-acarbose 88 Mass fingerprinting 2225 Maltose 1451 Mass spectrometry (MS) 826, 1748, 2115, 2191, Maltose phosphorylase GSG4-P 2345 2193, 2216, 2230 Index I 2861 MBP-dependent cell-mediated cytotoxicity (MDCC) C-Methyl-branched sugars 306 2451 Methylcelluloses (MC) 1506, 1508, 1521 MBP-trimer 2450 Methylcyclohexane 5 MCBs 1687 exo-Methylene 314  MeCN 1326 2,2 -Methylenedifuran 927 Melezitose 71, 1180 Methylfucosamine 907 Melibiose 71 N-Methylfucosamine 905 Melting point 823, 1477 Methyl-β-D-galactopyranoside 1115 Membrane 2140 Methyl-β-D-glucopyranoside 1115 outer 1608 4-O-Methyl-D-glucuronic acid 1489 Membranous cytoplasmic bodies (MCBs) 1687 2-O-Methyl-D-glyceraldehyde 884 Mercaptolysis 671 Methyl-α-D-mannopyranoside 1113, 1115 Mercerization 1481 Methyl-β-D-ribofuranoside 1117, 1121 Merrifield resin 472 Methyl-β-D-ribopyranoside 1117 Mesophase transitions 1623 4-C-Methyl-D-ribose 891 MeSOTf 1330 Methyl-β-D-xylopyranoside 1117 Messenger-RNA 67 Mevalonate, isotope-labeled 1035 Metabolic efficiency 2143 MHC 2659, 2661, 2669 Metabolic engineering 2133, 2421 MIC-1 2125, 2127 Metabolic precursors exogenously supplied 2137 Micelles 2153 Metal addition 907 Michael addition 835, 1982 Metal chelating 2422 Michael reaction 1046, 2301 Metal transition 253 Michael-aldol reaction 1983 Metallo-carbene 393 Microarrays 1233, 2115, 2118 Metastasis 2647 Microbial carbohydrate polymers 2457 Metathesis 1245 Microdomain formation 1624 Methacrolein 892, 894 Microfibrils 1483 p-Methoxybenzyloxymethyl ether 128 Microflora 1188 2-(Methoxycarbonyl)-ethylidene 123 Microheterogeneity 1737, 1797 2-Methoxy-1,3-dimethylhexahydropyrimidine 11 Micromonospora sp. 1964 2-Methoxy-1,3-dioxane 11 Microreactor 1241 Methoxyethoxymethyl ether 128 Microwave heating 463, 678 Methoxymethyl ether 128 Migita–Stille coupling 805 3-Methoxy-2-pyridyl (MOP) glycosides 568, 645 1,2-Migration 260 2-Methoxytetrahydropyran 9 Mimotopes 2104 Methyl aldofuranosides 29 Mithramycin 2559, 2562, 2608 Methyl 3,6-anhydro-2-deoxy-L-allo-heptanate 926 Mitsunobu protocol 162, 241, 681 1β-Methyl carbapenem 1052 Mitsunobu-type reactions 297 Methyl 6-deoxy-2,3-di-O-(t-butyldimethylsilyl)-α-D- Mizoroki–Heck reaction 803 glucopyranoside Mocdene 123 1049 Modulator, negative 2475 Methyl 2-deoxy-2-phthalimide-D-glucopyranoside Moenomycins 1557, 1559, 2571, 2573 1959 Moisture control 844 Methyl ethers 107 Molar substitution 1508 Methyl β-D-galactopyranoside 977 Molecular dynamics 4, 44 Methyl α-D-glucopyranoside 959 Molecular imaging 2115 Methyl β-D-glycero-D-guloseptanoside 31 Molecular mechanics 4, 44 Methyl α-D-glycero-D-idoseptanoside 31 Molecular modeling 42, 2297 Methyl α-D-mannopyranoside 969 solvent effects 43 Methyl 3-O-methyl-α-D-arabinofuranoside 29 Monobenzylation 829 Methyl α-L-rhamnopyranoside 1117 Monoclonal antibodies (mAbs) 1874 Methyl α-D-vicenisaminide 943 Monodisperse 1477 Methyl α-D-xylofuranoside 30 Monolayers, self-assembled 2581 2862 I Index Monosaccharides 841, 2221, 2252 Myeloblast 2474 biomedical applications 2400 Myrtenal 896 phosphorylated 2436 profiling 1876 N-TFAc sialyl donor 1338 scaffolds 995 NA inhibitor 1937, 1942 sulfated 2436 NAD+ 67 S-Monosaccharides 664 NADH/NADPH 67 Monothioglycosides 664 Naked sugars 917, 920, 924 Montmorillonite, K-10 544 NANA 21 MOP glycosides, unprotected 646 Nanocrystals 1491–1493 MOP glycosyl donor 646 Nano-electrospray 2196 Morphine 2626 NanoLC-ESI-MS 2214 Morphine β-6-glucuronide 2627 (2-Naphthyl)methylene acetals 119 Morpholine-N-oxide 1494 Naphthylthio glycoside 1288 MRI contrast agents 2175 Naringenin 2598 mRNA level 2154 National Institutes of Health (NIH) 2186 mRNA transcription 2452 Natural killer (NK) cell 2624 MS 2117, 2192, 2205 Natural products, glycosylated 2547 Mucin glycopeptides 1273, 1780, 1812, 1819, NCL 1838, 1840 2648, 2658, 2669 cysteine-free 1801, 1840 Mucin glycoproteins 1846 Nef 888 Mucin glycosylation 2656 Negishi coupling 805 Mucin-based vaccines, design 2667 Neighboring group participation 573, 582, 665, 1151 Mucins 1742, 1753, 2133, 2648 Neisseria meningitidis 2700 Mucin-type O-glycans, biosynthesis 1754 Neocarzinostatin 2568, 2601, 2604 Mucolipidoses 1685, 1788 Neoglycoconjugates 2097 Mucopolysaccharidoses 1685 Neoglycolipid (NGL) 2122 Mukaiyama reaction 761, 896 Neoglycopeptides 1851 Mulberry 1904 Neomycin 2570 Multivalency 1011, 1786, 2097, 2581 Nephritogenoside 1741 Multivalent display 2122 Neu5Ac 1315, 1877, 2045 Mur enzymes 2-phenylselenyl derivative 1332 peptidoglycan biosynthesis 1543 α-thioacetate 1354 Muramic acid 2-trifluoroacetimidate derivative 1335 bacterial peptidoglycan 1542 Neu5Gc 1315, 1877 Murein 77, 84, 1427, 1542, 1760, 2355 Neural membranes, embryonic 2150 Murein-peptidoglycan 81 Neuraminic acid 1396, 2085 Muscari sp. 1897 Neuraminidase 1933, 1935, 2390, 2434 Mushroom-shaped spike 1936 Neuraminidase inhibitors 1914, 2082, 2391 Mutansucrase 75 oseltamivir 2391 Mutarotase 64 zanamivir 2391 Mutarotation 1156, 2001 Neurodegenerative diseases 1684 L-Mycarose 710 Neurokinin receptor antagonist 1064 Mycobacteria 1607 Neurological disorders 1901 cell wall polysaccharides 1571 NGL technology 2123 Mycobacterial infections 1581 NGL-based microarray 2124 Mycolata 1571, 1580 NHS activated slides 2128 Mycolic acids 1573, 1621 Nicholas reaction 778 Mycoloyl arabinan 1646 Nickel catalyst 805 Mycolyl arabinogalactan 1607 Nicotinamide 2633 Mycosamine 1299, 2612 Nicotinamide adenine dinucleotide 66 D-Mycosamine 2613 NIPAm 1273 Myelin-associated glycoprotein 2102 NIS-TfOH 1327, 1328 Index I 2863 Nisin 1554 Nucleophilic additions 306, 882, 892 NIS/TESOTf 604 Nucleophilic participation 1320 NIS/TfOH 602 Nucleophilicity 231, 2001 NIS/Yb(OTf)3 592 Nucleosides 305, 307, 308, 321, 324–330, 336, Nitrile effect 463 493, 1119, 1120, 2002 Nitrile oxide 1055, 1917 Nucleotide glycosidation 493 Nitrile solvent effect 1316, 1326 Nucleotide sugars 1860, 2252 Nitriles, electron-deficient 456 Nutrition 842 Nitrilium intermediate 1327 Nystatin 2612 3-C-Nitro glycals 720 Nägeli amylodextrin 1460 Nitroaldol 888 condensations 893 Octanediol 1245, 1254 6-Nitro-2-benzothiazolyl glycosides 568 Octitols 1093 1-O-(p-Nitrobenzoyl)glycosyl donor 545 Octose 1400 p-Nitrobenzoylxanthates, rearrangement 683 Octreotide 2581 p-Nitrobenzyl 115 OGT 2169 Nitrocellulose 2123 OH group, free 288 Nitrogen bases, solid-supported 460 Okadaic acid 2556 Nitromethane 888 Oleandomycin 2551 Nitromethyl sugars 2032 Olefin metathesis 2022, 2056, 2093 O-Nitro-phenoxyacetate 1243 Olefination 899, 901 Nitrosugars 816, 834, 2022 Olefins, prochiral 1056 6-Nitrothiazolyl mannoside 1292 Olestra 1147 NMR spectroscopy 25, 38, 826, 1261, 2453 Oligodextrans 2360 Nod factors 2597 Oligogalacturonates 609 Nodulation factor 604 Oligomannose-type 1750 NOEs 1967 Oligomers Nogalamycin 2637 amide-linked 2082 Nogalamycine 2607 C-Linked 2067 Nojirimycin 868, 899, 1889 Oligosaccharide syntheses, solid-phase 469 Nonderivatizing solvents 1484, 1493 Oligosaccharide synthesizer, automated 1252 Noniterative synthesis 928 Oligosaccharides 452, 1163, 1185, 1186, 1200, Non-Leloir transferases 1783 1363, 2359, 2670, 2707 Non-natural sugar 2133 animal feed 1199 Nonreducing end 1414, 1415 asn-linked 1307 Nonreducing sugars 691 bioactive 2358 Non-starch polysaccharides (NSP) 1514 library 1207, 1236 Nonwovens 1495 C-linked 2022 Norjirimycin 11, 924 microarrays 2173 Nortropanes 1898 mimetics 2079 L-Norvaline 874 prebiotic 1186 Notch 2283 recognition 2122 Novobiocin 2008 reducing 2124 Novozyme 435 936 C-Oligosaccharides 2021 NPG, sidetracked 578, 603 Oligosaccharyltransferases (OT) 1740, 2573 NPGs, tetrachlorophthaloyl 584 L-Olimycose 910 NPOE 592 Oliose 937 Nuclear Overhauser effect 40, 826 Olivomycin 2559, 2608 Nuclear proteins 1757 Olivose 710, 937, 2609 C-Nucleophile 329 One-pot reactions 666, 667, 1039, 1051, 1207, Nucleophiles 235, 277 1369 organocuprate 277 δ-Opioid receptor 1841 trivalent phosphorus-containing 263 Optical rotation 1156 2864 I Index Optical rotatory dispersion (ORD) 42 Papulacandines 2558 Oral treatment 1902 Papyrus 78 Organic esters 1499, 1501 Para-crystallinity 1489 Organoaluminum reagents 768, 782 Pathogen 2391 Organocopper reagents 776, 781, 1050 Paucimannosidic 2277 Organosilane 768 Payne rearrangement 899 Organosolv pulp 1488 PCR 2116 Organotin reagents 109, 768 Peak lists 2228 Organozinc reagents 776 Pearlman’s catalyst 1715 Orthoester 1713 Pectate lyases 2339 Orthogonal chemical functional groups 2156 Pectenotoxin 2556 Orthogonal protecting groups 624 Pectic oligosaccharides 1196, 1197 Orthogonal sets 137 Pectic substances 1425 Orthosomycin antibiotics 2552 Pectins 79, 1197, 1425, 1491, 1522, 2365 Osladin 2559, 2619 high-methoxyl (HM) 1523 Osmium(VIII) oxide 197, 199 low-methoxyl (LM) 1523 Overexpression 2170 Pelargonin 2548 Overman rearrangement 389, 999 Penicillin binding proteins 1549 thermal 1032 inhibitors 1554 7-Oxabicyclo[2.2.1]hept-2-enes 917 Pentadecane-octols 927, 930 7-Oxabicyclo[2.2.1]hept-5-en-2-one 919 (E)-Penta-2,4-diene 915 8-Oxabicyclo[3.2.1]octan-3-one 926 Pentahydroxyindolizidine 923 8-Oxabicyclo[3.2.1]oct-6-en-3-one 924 Pentasaccharides 1157 Oxadienes 914 n-Pentenoyl esters 160 Oxathiines 568 Pentenyl arabinofuranosides 593 Oxazolidinone 894 n-Pentenyl arabinofuranosides 591 5-N-4-O-Oxazolidinone 1347 n-Pentenyl furanosides 590 sialyl donor 1318 n-Pentenyl galactofuranosides 591 Oxazolidinones, bicyclic 1040 Pentenyl glycosides 568 Oxazoline 1829 n-Pentenyl glycosides 160, 569, 747, 1245, 1711 Oxecane 7 n-Pentenyl orthobenzoate 1298 Oxepanes 30 n-Pentenyl ribosides 590 pseudorotation 31 Pentosans 1530 twist chair 31 Pentose enzymes, transporters, receptors 2404 Oxetane 999, 2087 Pentoses 63, 65, 864, 2401, 2407 Oxidation-reduction 1173, 1295 metabolism 2402 Oxidations 1431, 1462 Pentraxin, neuronal activity-regulated 2469 platinum-catalyzed 189, 193 Pentraxins 1786 Oxidative degradations 384 Peptide N-glycanases (PNGases) 1747 Oxidative hydrolysis 578 Peptides 885, 2719 Oximes 206 conformation 1778 ligation 2124 isosteres 995 Oxionium cation 440 mimetic 1005 Oxocarbenium ion 764, 772, 1992 secondary structure 1777 4-Oxovancosamine 2574 Peptidic oligosaccharide mimetics 2104 Oxyamino-linked sugars 2093 Peptidoglycan 1226, 1427, 1536, 1542, 1621, 1760 (S)-Oxybutynin 1064 biosynthesis 1554, 1761, 2575 biosynthesis, intracellular steps 1543 Palladium 181, 322, 802 drug target 1554 Palytoxin 2558 length of glycan chains 1547 Pantothenic acid 2632 orientation of glycan strands 1548 Paper 1439 peptide chain composition 1542 PAPS 1377 synthesis of large fragments 1553 Index I 2865 synthetic substrates for studying biosynthesis Photo-affinity labeling 2456 1545 Photobromination 201 thickness, degree of crosslinking 1548 Photosynthesis 1439, 1474 Peptidoglycan glycosyltransferases 1549 Physiological conditions 2179 Peptidomimetics 995, 997, 1023 Phytomass 381 Peptidosaccharides 2082 PIA 1585 Peracetylation 2141 PILAM 1581 Peracetyl-2-hydroxy-D-glucal 707 PIMs 1651 Periaxonal architecture 2476 Pinacol coupling, SmI2-mediated 1988 Periplasmic binding proteins 2405 (S)-Pinanediol 884 Permethylation 2199 Piperidine alkaloids 1042 Perseitol 1093 Pivaloyl group 134 Petasis reagent 762 p-Pivaloylaminobenzyl 115 pH ranges 2176 Placental barrier 2591 Pharmacophore 2452 Plakoside A 1639 mapping 995 Plane polarized light 60 Pharmacophoric groups 1015 Plant components 512 Phase angle 28 Plantagoside 2596 Phase separation 468 Plasmodium falciparum 1717, 2719 Phase transition behavior 1622 Plasticization 1505 Phenol-sulfuric acid micro method 1465 internal 1505 Phenoxythiocarbonyl groups 1321, 1322 Plasticizer 853 Phenylethyl glycosides 2548 PNAG 1585 β-Phenyl-GABA 1066 PNBP test 1264 6-Phenyl-galacto-2-hexulose 868 PNGase 1878 Phenylmethyl sulfonic acid ester 1048 Podand 1269 Phenylseleno-glycoside 785 Podophylotoxin 2599 Phenylselenyl 1321, 1323 Polarizing microscope 1445 Phenylsulfenyl 1321 Poly-N-acetyllactosamine 1370, 1752, 1755 Phenylsulfonylethylidene 122 Poly-N-acetyllactosaminoglycans 2279 Phenyl-1-thio glycosides 643 Polyamides 2081 Pheromone 1052 Polycyclic scaffolds 1018 Philippine natural grade (PNG) carrageenan 1527 Polydeoxyalditols, long-chain 927 Phosphate ester 151 Polydextrose 1516, 1531 Phosphate starch esters 73 Polydispersity 1417 2-5-Phosphate-5-thio-D-erythro-pentose 871 Polyene macrolides 930, 2612 Phosphatidylinositol mannoside 1577 Polyethylene glycol monomethyl ether (MPEG) Phosphinothioester 1804 1264 Phosphite 1292, 1333 Polyethylene glycol (PEG) 1256, 1307 Phosphitylation 1708 Polyhydroxy aldehydes 60 Phosphoethanolamine 1711 Polyhydroxy nylons 2100 3-Phospho-D-glyceraldehyde 62 Polyketides 927 3-Phospho-D-glyceric acid 62 Poly-D-mannopyranosyluronic acid 82 1-Phospho-D-glycerol 62 Polymer blotting method 1269 Phosphoglycerolipids, glycosidated 488 Polymer scaffolds, synthetic 2476 Phospholipid 1707 Polymerization 1477, 2081, 2384 Phospholipidation 1713 Polymers 2015, 2150 Phosphoramidate 1292, 1707 Polymer-supported strategy 1218 Phosphorolysis 2328 Polymer-supported synthesis, soluble 1210 Phosphorus 264 Polymorphism 1482, 2647 Phosphorylase 1452, 2342 Polymyxin B 1569 Phosphorylation 151, 646, 1848, 2148 Polyols 841, 848 Phosphorylcholine 2277 1,3-Polyols, long-chain 928 2866 I Index Polyoses 1488 Protecting groups 106, 665 Polyoxin antifungal 912 Protein kinase 2548, 2549 Polyphenols 2592 Protein ligation, expressed 1805, 2388 Polyproline type II helix 1775 Proteinaceous inhibitors 2352 Polysaccharides 1126, 1475, 2251, 2339, 2380, Protein-carbohydrate 2581 2707 Protein-polysaccharides 1416, 1525 capsular 2391 Proteins chitin 2382 folding 1786 chitosan 2382 physicochemical properties 1773 extracellular 1536, 1586 stability 1775 glycosaminoglycans 2383 Proteoglycans 496, 1416, 1418, 1420, 1421, 1758, Hib 2392 2286 lipo 2392 Proteomics 2116, 2178 neutral 2340 Protic acids neutral polysaccharide 2381 heterogeneous 446 occurence 1413 homogeneous 446 properties 1413 Protonation trajectories 2337 significance 1413 Protozoa 1618 O-specific 1608 PSA, inhibition 2147 synthetic 2384 P-selectin 1844, 2100 Polysialic acid 1373 Pseudoaxial 12 Polysialyl side chains 1751 Pseudodisaccharide 1708, 2093 Polystyrylboronic acid 1245 Pseudoenantiomeric 1036, 1039, 1057 Polyurethanes 2092 Pseudoequatorial 12 Post-release purification 1879 Pseudomonas amyloderamosa 1453 Post-synthetic modifications 2136 Pseudomonas cepacia lipase 935 Post-translational modification 1737 Pseudooligosaccharides 2569 Potassium permanganate 186, 199 Pseudopeptide 1005 Potassium thiocyanate/DMSO 1486 Pseudoplastic 1498, 1519 Potato amylose 1441 Psicose 863, 875 Potato phosphorylase 1456 Psyllium gum 1530 Prebiotic conditions 879 Ptyalin 2621 Prebiotics 1186–1188, 1198, 2358 Pullulan 75, 1528 (ent)-Pregabalin 1066 Pulp production 1476 Primers, putative 1456, 1458 Pumiliotoxin C 1041, 1042 Process analytical technology (PAT) 1876 Pummerer rearrangement 899 Processed Euchema seaweed (PES) 1527 Pyran 999 Prodrugs 2141, 2564 Pyranose 2-oxidase 195 Prokaryotes 2251 Pyranose ring Proline 873, 875, 878 A values 16 (S)-Proline 875 boat conformation 15 Promoter 1680 chair conformation 15 Propargyl ethers 119 skew conformation 15 Propargyl glycosides 653, 1246 Pyranoses 63, 434 Propargyl silane 769 Pyranosides 1113 Propargyloxycarbonyl 140 Pyranosyl 2-pyridyl sulfones 2039 4-(Propargyloxycarbonyl)benzyl glycoside 1247 Pyridine thioglycosides 645 Propylene glycol alginate 1522 Pyridinium chlorochromate 183 Propylene oxide 1463 Pyridinium chloromate 191 Prosaposin 1683 Pyridinium dichromate 183, 187, 191, 827, 1462 Proteases 133, 1011 Pyridoxine 2629 O-Protecting group 460 Pyridyl sulfone 2040 Protecting group, permanent 108 2-Pyridyl sulfones, anomeric 2043 Index I 2867 Pyrolysis 739, 749 Recombinant therapeutic glycoprotein 1874 5-(Pyrrolidin-2-yl)tetrazole 874 Reducing end 1414, 1747 Pyrrolidones 908 Reducing sugars 844 Pyrrolizidine 1895 Reducing value 1464 Pyruvate ketals 125 Refined sugar 1166, 1168 Pyruvate kinase 868 Reformatsky reaction 1070 Reformatsky-type coupling reactions, samarium Q-enzyme 1459 mediated 1356 Quadrupole analyzers 2197 Refractive index 823 Quasi-mirror image 1038 Regenerated cellulose product 1499 Quercetin 2593 Regioselective coupling 598 Quercetin 3-rhamnoside 2598 Regioselectivity 107, 468, 599, 1094, 1101, 1388, Quinic acid 1939, 1941, 1944, 1945, 1947, 1948 1389, 2182 D-Quinovose 87 Relaxation 40, 41 Relenza 1914 Radical initiator 833 ReLPS 1647 Radical species 1050 Remote activation 645 Radicals 330, 415 Remote control 465 Radiolabeled probes 2145 Remote functionality effect 1338 RADO(Et)OH 917 Renin-binding protein 2152 Raffinose 70 Repeat units 1488 Rafts 1624 Residues 2227 RAMA 867 Resin glycosides 512 Ramachandran plot 33 Resistance 1762 Raman optical activity 1156 Respinomycin 2637 Ramberg–Bäcklund rearrangement 726, 794, 2034 Retention 455 Ramoplanin 1554, 1837 Retinoid glucuronides 2634 Random coil 1450 Retinol 2633 Raney nickel 202, 209, 214 Rat testis Gal receptor (RTG-r) 2456 Retroviruses 2570 Raw sugar manufacture 1165, 1166 Reverse anomeric effect 19, 1327 Reaction RGD mimetics 2580 addition 237 RGD sequence 2579 Arbuzov 266 Rhamnogalacturonans 1425, 2289 epoxide-opening 234, 248 Rhamnomannans 1427 α Michaelis–Arbusov 263 -L-Rhamnopyranosyl 537 ring-opening 234 Rhamnose 1269 Reactivity tuning 1345 biosynthesis of mycobacterial wall 1575 Reagent array analysis method (RAAM) 1748 Rhamnotriose 534 Real-time monitoring 480 Rhamsan 84 Rearrangement 332 Rheology modification 1499, 1505 Ferrier 237 Rhizobium 2597 intramolecular 235, 829 Rhizopus delemar 1452 long-distance 261 Rhodium 318 molecular 233 Ribitol (adonitol) 87, 898, 1088 Overman 256 Riboflavin 2630 radical-induced 262 D-Ribofuranoside 2002 Rebeccamycin 2549, 2628 D-Ribonic acid 1098 Receptors D-Ribono-1,4-lactone 2004 ligands 1011 Ribonuclease (RNase) 1776 mannose-6-phosphate 1788, 1846 Ribonucleosides 1120 oligomerization 2461 Ribose 65, 876, 891, 893, 962, 1132 recycling 2462 D-Ribose-5-phosphate 66 Reciprocal donor acceptor selectivity (RDAS) 598 Ribosides 2626 2868 I Index

L-Ribulose 875 Salmonella O-antigens 85 D-Ribulose-1,5-bis-phosphate 66 Samariation, reductive 2039, 2043 D-Ribulose-5-phosphate 66 Samarium diiodide 794 Ricin 2447 SAMP 896 Ring Sandhoff disease 1687 five-membered 236 Saponins 514, 1611, 2559, 2618 six-membered 236 SAR 1940, 1952, 2592 sulfur-containing 248 Scaffolds 995 three-membered 236 natural product-like 1020 Ring cleavage 2200 Scanning densitometry 91 Ring contractions 394 Schardinger dextrins 75 SmI2-mediated 1989, 1992 Schiff base 846 Ring expansions 398 Schistosoma 1616, 1618 Ring transformation 404 Schizophyllan 1264, 2381 Ring-closing metathesis (RCM) 301, 366, 1021, Schweizer’s reagent 1485, 1495 1924, 2056 Scilla spp. 1897 Ring-closing rearrangements 393 scyllo-Inositol 1109 Ring-opening, Pd(0)-promoted 1990 Seaweed flour, alkali-modified 1527 Ring-opening polymerization 284 Secondary metabolites 2549, 2550, 2558 Ring-opening rearrangements 404 Secondary structure 2087 Rink resin 1017 Secretion 1908 Ristocetin A 2573, 2574 Seeds 1438 Ritter reaction 760 Selectins 1788, 1843, 2098, 2390 RNA 67, 2562, 2570 Selenium 260 binding 2090, 2571 Selenoglucosan 751 interaction with 2570 Selenoglycosides 663, 1707 messenger-RNA 67 Seleno-Pummerer rearrangement 919 ribosomal-RNA 67 Semi-automatic sequencing 2225 transfer-RNA 67, 1864 Semiorthogonal donors 587 RNA polymerase 1848, 2168 Septanoses 30 tRNA suppressor 1851 twist chair 31 tRNA/tRNA synthetase 1851 Sequence analysis 2224 RNase 1746, 2547 Sequons 1740, 1741 ROESY 41 Serinal 903 Roots 1439 Serine 874, 886, 2652 Rosette terminal complex 1483 Serum amyloid protein (SAP) 2468 Rossmann-type fold 2291 Sharpless aminohydroxylation, Rotameric conformations 22 enantioselective 945 Rotational entropy 2456 Sharpless asymmetric dihydroxylation 940 Rubusoside 2620 Sharpless dihydroxylation, enantioselective 940 Ruff oxidative degradation 386 Sharpless epoxidation 291, 399 Ruthenium(VIII) oxide 183, 186, 191, 199 selectivity 291 Rutin 2631 Sharpless procedure 349 Rydon reagent 242 Shear thinning 1498, 1507 Shigella dysenteriae type 1 1830, 2185 Saccharide-peptide hybrid 2082 Shikimic acid 1938, 1945, 1947, 1948 Saccharomyces cerevisiae 1713, 2249, 2268 Shingolipisosis 1685 Saccharomycins 2554 Short chain fatty acids (SCFAs) 2140 Saccharopeptides 2082 Sialic acid 20, 24, 197, 531, 865, 866, 1315, 1877, SADO(Et)OH 917 2433, 2656 Safety catch 1256, 1866 aldolase 865 Salicin 2548 biomedicine 2435 Salicortin A 2548 biosynthesis 2148 Index I 2869 C-5 modified 2158 Small’s soluble starch 1460 C-9 modified 2160 SmI2 407, 1983 1,5-lactamized 1347 SN1 mechanism 2303 oligomer 1343 SN2 mechanism 1299, 2299, 2303 pathway 2139 SN2 mechanism 667 peracetylated 2160 Sodium borohydride 202–205, 209, 214 residues 1616 Solanaceae 1898 side chains 24 α-Solanine 2619 Sialidases 1396 Solasodine 2619 trans-Sialidase 1399 Solid phase 1039, 1378 Sialoglycoconjugates 2436 Solid-phase peptide synthesis (SPPS) 1799, 1866 Sialoside acceptor, 1,5-lactamized 1352 Solid-phase synthesis 628, 691, 1006, 1210, 1212, Sialosides 379, 1316, 2153 1221, 1241, 1717, 1721 Sialuria 2153 Solubility 1503 Sialyl donors Soluble polymers 1264 C1-appended 1324 Soluble supports 480 C3-appended 1321 Solution-phase 1378 C5-modified 1318, 1336 Solvent effects 462 Sialyl C-glycoside 1355 reaction-field model 43 Sialyl Lewisx (sLex) 997, 1752, 1788, 1843 Somatostatin 996, 998, 2581 Sialyl pentenoate 550 Somoygi–Nelson method 1464 Sialylation 1274, 1632 Sonication 666 α-2,6-Sialylation 2172 Sonogashira reaction 1247 Sialyl-TN 1341, 1755, 1811, 1819, 2389 Sorbitol 849, 1092 Sialyltransferases 1269, 1677, 1679, 2084, 2279, Sorbose 863 2294 Soybean agglutinin (SBA) 1737 human 2150 Spacers, noncyclic 2099 Sia5TGc 2179 Spectinimycins 2570 Siglec-Fc chimeras 2472 Spectral matching 2237 Siglecs (sialic acid binding immunoglobulin-like Sphingoglycolipids 1631 lectins) 2125, 2470 Sphingolipid activator proteins 1683 Sigmatropic rearrangements 355, 387, 798, 799, Sphingolipidoses 1685 1933 Sphingomyelin 1616 Signal peptide 2463 Sphingosine 1616, 1675 Signaling 2648 Sphingosine-1-phosphate 1675 Signature sequence 2468 Spin-lattice relaxation rates, nonselective 1152 Silaketal 1303 (–)-Spinosyn A 537 Silica-gel, multiple ascent 91 Spirocyclic 1020 Silicon tether 789 Spirocycloheptadiene, optically active 1977 Silver oxide 1282 Spiro-hydanthoin 2579 Silver salt, insoluble 1282 Spiroketal glycosides 2558 Silver silica-alumina 1284 Spiro-ortholactone 2552 Silver silicate 1284 Stachyose 70 Silver zeolite 1284 Stannyl ethers 192 Silybin glycosides 2595 1-Stannyl glycal 712 Silyl enol ether 769 Stannylene acetals 192, 1302 Silyl ethers 144 Staphylococcus aureus 1760, 1762 Silylacetylene 769, 777 MRSA resistant 1763 Silylation 144 Starch 72, 274, 845, 1426, 1447 α-Silyloxy acetaldehyde 877 amylose and amylopectin 1447 Singlet oxygen 1957 biosynthesis 1456 Sisomycin 2570 commercial soluble 1460 Skew 4, 15 oxidation 1462 2870 I Index pyrolysis 274 oligosaccharides 1178 solubilization 1445 physico-chemical properties 1170 thin-boiling 1461 production, industrial 1165 Starch acetates 1462 Sugar alcohols 86, 1080 Starch branching enzyme 1468 Sugar aldehydes 285, 315 Starch chemistry, analytical methods 1464 Sugar allyltin derivatives 364 Starch fractions, degree of branching 1466 fragmentation 364–366 Starch granules hexose-derived 365 crystalline parts 1444 Sugar amino acids 996, 2079, 2578 gelatinization 1445 Sugar diphosphinite 1057 isolation 1439 Sugar diphosphites 1059 pulsing 1457 Sugar enones 835 scanning electron micrographs 1442 Sugar ketone 315 Starch synthase activity 1468 Sugar lactones 760 Starch synthesis, inhibition 1458 Sugar libraries 2638 Starch-binding domain (SBD) 2357 Sugar mimics 366 Staudinger ligation 1850, 1861 Sugar monophosphites 1067 traceless 1804 Sugar nucleotides 1366, 1783 Staudinger reaction 1006, 2178 Sugar organometallic 2022 Staurosporine 2549 Sugar oxazoline 1828 Steeping 1439 Sugar phosphates 862 Stem cell 2182 Sugar phosphine oxide 1063 Stereoelectronic effects 764, 768, 771 Sugar phosphine-phosphites 1059 Stereoselectivity 1389 Sugar phosphinites 1056 Steric hindrance 1150 Sugar phosphoranes 359 Steryl biosides 1611 Sugar stannanes 297 Steryl glycosides 1611 preparation from anhydrosugars 297 Stevioside 2620 synthesis of C-glycosides 299 Stille coupling 940 Sugar sulfoxides 712 Strecker synthesis 1037, 1063, 1065 Sugar thioether-phosphinites 1059, 1062 Streptamine 2570 Sugarbeets 1168 Streptidine 2569 Sugar-peptide hybrids 996 Streptococcal polysaccharides 534 Sugars 841 Streptococcus mutans 74 1-O-acylated 435 Streptococcus pneumoniae 2700 amino 251 Streptomycin 2569, 2615 chlorodeoxy 243 Streptose 837, 2569 stereoselectivity of epoxidation 288 Structural mimetics 2080 unsaturated 249, 259 Structural support 1475 2,3-unsaturated 288 Structure builders 2232 L-Sugars 848, 997 Structure-stability 2358 Sulfatides 389, 1676 Subsites 2329 Sulfation 1430, 1759 Substitution 231, 251, 258, 262 1-Sulfenates, rearrangement 682 nucleophilic 229 Sulfite pulp 1488 Substrate recognition 2353 Sulfites 289 Substrate reduction 1905 Sulfoglycosphingolipids 1618 Subtilisin 1807 γ -Sulfones 1047 Succinoglycan 1529 Sulfoquinovosyldiacylglycerol 1605 Sucraflate 1144 Sulfotransferases 2288 Sucralose 71, 1148, 1175 Sulfur (electronegativity) 1154 Sucrase 1981, 2090 Sulfur-transferring reagent 681 Sucrose 69, 70, 1122, 1163, 1164, 1168 Supramolecular arrangements 1604 analysis 1171 Supramolecular structure 1619 Index I 2871 Surface plasmon resonance (SPR) 2455 2,2,6,6-Tetramethyl-1-piperidine oxoammonium ion Suzuki–Miyaura coupling 763, 805, 1043, 1045 (TEMPO) 188, 190, 191, 1462 Swainsonine 1894 Tetrapeptide core, acylated 1608 Sweetener 2432 Tetrapropylammonium perruthenate 184, 186, 191 Sweetness 851 Tetrasaccharides 1157 Swern oxidation 894 Tetrodotoxin (TTX) 356, 2556 Swinholide A 2558 Tetroses 898, 899 1,3-Synaxial repulsive interactions 18 TEV protease 1805 Syndiotactic 1476 Theanderose 1180 Synperiplanar lone-pair hypothesis (SLPH) 586 Thermal degradations 381, 1484 Synthesis based on affinity separation (SAS) 1267 Thermal hysteresis 1774 Synthesis, polymer-supported 1241 Thiabutadienes 914 Synthetic anti-endotoxin peptides (SAEP) 1569 Thiamine 861, 873, 2628, 2629 Thiazole-based method 886 T-cell receptors 2658, 2661 1,3-Thiazolidine-4-carboxylic acid 874 TAAs 2658, 2668, 2670 Thiazoline 887 Tagatose 847, 863 derivatives 680 Tagatose-1,6-P2 aldolase 865 Thin-layer chromatography (TLC) 91 Tagging via substrate 2169 α-Thioacetal 877 Tags 1264 Thioacetic acid 677 Tamiflu 1066, 1914, 1915 3-Thio-N-acetyl-D-glucosamine 2012 Tandem aldol-Wittig type reaction 1971 Thioaldose 677 Tandem Mannich–Michael reaction 1041, 1043, Thioalkylation 681 1044 5-Thio-D-allose 2006 Tandem mass spectrometry 2198 4-Thio-D-arabinofuranose 2002 Tara gum 1519 5-Thio-D-arabinose 2005 Targeting 1787 4-Thioascorbic acid 2014 Tartaric acid 883, 899, 903 Thiocarbonylation 165 Tautomycin 973 Thiodisaccharides 1154 Tay–Sachs disease 1686 S-linked 835 TC conformation 30, 31 5-Thio-D-erythro-pentose 872 Tebbe’s reagent 358, 762 5-Thio-D-fructofuranose 2004 Teichoic acids 87, 1427, 2700 6-Thio-D-fructose 2007 Teichuronic acids 1427 5-Thio-L-fucopyranose 889 Teicoplanin 1763, 1832, 2573 5-Thio-L-fucose 2011 Temperature dependence 26 5-Thio-D-galactose 2006 Templates 2085 5-Thio-D-glucal 2006 TEMPO 188, 190, 191, 1462 2-Thio-D-glucitols 673 Temporary protection 116 5-Thio-D-glucopyranose 2002 Tencel 1494, 1496 Thioglucosan 750 Teniposide 2600 5-Thio-D-glucose 2005, 2011 Tetanus 2710 Thioglycolate-induced peritonitis 2466 2,3,4,6-Tetra-O-acetyl-D-glucopyranosyl Thioglycoligases 692 bromide 707 2-Thioglycoside sialyl donors 1326 Tetra-O-benzoyl-D-glucopyranosyl bromide 707 Thioglycosides 580, 588, 663, 744, 747, 1015, 2,3,4,6-Tetra-O-benzyl-D-glucopyranosyl 1289, 1708 iodide 707 Thioglycosynthases 692 Tetrabutylammonium fluoride/DMSO 1486 5-Thio-L-idopyranose 2001 1,1,2,2-Tetrachloroethane 1448 5-Thio-L-idopyranosides 2006 Tetrahydrofuran 12 Thiol approach, stannylated 666 Tetrahydropyran 7 Thiolactone 1302 Tetrahydropyranyl ether 128 Thiolevoglucosan 276 Tetraisopropyldisiloxane 149 Thiolglycolyl groups 2142 2872 I Index Thiols 835, 1154 Trafficking 1908 acceptor 684 Transacetalation 121 auxiliary 1803 Transamidation 1701 to Michael acceptors 682 Transcription factors 1681 5-Thio-D-lyxose 2005 Transcriptional regulation 1680, 1681 4-Thio-α-maltoside 1154 Transesterification 131 5-Thio-D-mannose 2006 Transferases 1229 Thiooligosaccharides 684 Transglutaminase 1863 Thioorthoesters, rearrangement 683 Transglycosylase 2571, 2573, 2575 4-Thiopentofuranoses 2003 Transglycosylation 1388, 1389, 1809 Thiophenyl glycosides, 2,3-unsaturated 719 Transition states 873, 2308 Thiophilic promoters 668 Transition-metal complexes 1055 5-Thio-D-ribose 2004 Transition-state analogues 1936, 2309 6-Thioseptanose 2007 Transition-state inhibitors 2350 Thio-L-sorbose 871, 2007 Transmetalation 791 Thiosugars 664, 816, 835, 836 Transporters 1228, 2254, 2413 5-Thio-D-threo-2-pentulofuranose 2003 Trehalamine 1967, 1969 Thio-trehalose 1155 Trehalase-specific inhibitory activity 1964, 1965 Thioureas 677, 2098 Trehalose 69, 72, 1122, 1964 5-Thio-D-xylopyranose 2002 Trehalostatin 1964, 1965 5-Thio-D-xylose 2003, 2004, 2011 Trehazolin 1913, 1915, 1951, 1964, 1965, 1967, 5-Thio-D-xylulose 2003 1969, 2088 Thixotropic 1498 C-6 epimer 1977 Thomsen–Friedenreich antigen 1390, 1816, 2068 C6-epimer 1973 Threitol 1083 intact 1979 D-Threonic acid 1096 2,3,4-Tri-O-acetyl-1,5-anhydro-6-deoxy-L-arabino- Threonine 2652 hex-1-enitol 706 D-Threose 62 Tri-O-acetyl-1,6-anhydro-β-L-idopyranose 742 Thy-1 1714 Tri-O-acetyl-D-galactal 976 Thymol 1448 Tri-O-acetyl-D-glucal 959 Thyrotropin 2457 2,3,4-Tri-O-acetyl-L-rhamnopyranosyl TiCl4 408 bromide 706 Time-of-flight (TOF) analyzers 2196 Triacylglycerol 62, 86 Tin 293 Trialkylstannyl ether 109 organotin derivatives 293 3,4,6-Tri-O-benzyl-D-glucal 703 stannyl intermediate 294 Tributyltin hydride 211, 214, 216, 217, 326, Tissue infusion and preservation 2426 785, 833 Tissue plasminogen activator (tPA) 1777 Trichloroacetimidates 457, 626, 671, 685, 1251, TLC separation 91 1293 Tmb 1841 formation, one-pot 460 TN antigen 1742, 1753, 1812, 2282, 2652 glycosyl donor 1335 Tocopherol 2634 Trichloroacetonitrile 456 p-Toluenesulfonylimidoosmium reagent 254 2,2,2-Trichloroethoxycarbamoyl (N-Troc) group α-Tomatine 2619 1339 Tool-kit 2186 2,2,2-Trichloroethyl carbonate 140 Torsional angle, ω 32, 43 Trichloroimidate glycosylation 1714 Torsional disarming 577 2,4,6-Trichlorotriazine 1463 Torula yeast 1491 Trichomes 1475 Tosylation 1150 Triethylsilane 213, 764 stereoselective 828 α-Triflate 635, 643 Tosylhydrazone 265 Trifluoroacetonitrile 516 Toxoids 2710 2,2,2-Trihaloethylidene acetals 127 Toxoplasma gondii 1714, 2125 Triisopropylsilyl (TIPS) group 148 Index I 2873 4,5,6-Trimethoxy-2-mercaptobenzyl (Tmb) 1802 palladium-catalyzed reactions 371 1-O-Trimethylsilyl derivatives 670 preparation of 346 2-(Trimethylsilyl)ethoxymethoxybenzyl ether 115 Uridine 325, 1119 Trimethylsilylethoxymethyl ether 128, 129 Uridine diphosphoglucose (UDPGlc) 67 2-(Trimethylsilyl)ethyl glycosides 160 Uronic acids 187, 188, 201, 203, 1416, 2079, 2433 Triphenylmethyl ether 118 2-Urosyl bromide 1299 Trisaccharides 36, 1157 Tris(alkoxy)benzylamine 1244 V3 domain 1829 Tris(2-carboxyethyl) phosphine hydrochloride Vaccines 1220, 1810, 2389, 2391, 2581, 2658, (TCEP) 2180 2702, 2706 Trityl ethers 118 bacterial capsular polysaccharides 1590 Trityl perchlorate 540 bacterial lipopolysaccharide 1570 Trityl tetrakis(pentafluorophenyl)borate 551 mucin-based 2670 Tritylation 118 recombinant 1947 selective 1150 Valency 2455 Trypanosoma brucei 1705, 1744, 2009, 2011 (+)-Validamine 1982, 1983 Trypanosoma cruzi 1721 Validamycins 836 Tryptophan 2547 (+)-Valienamine 1982, 1983 Tryptophan glycoconjugates L-Valine 874 C-linked 493 Valonia ventricosa 1476 N-linked 493 Value-added products 1174 Tsuji–Trost reaction 802 Van der Waals bond 1480 Tuberculosis 1581 Vancomycin 1554, 1763, 1831–1833, 2554, 2571, drugs and drug resistance 1580 2573–2575, 2613 Tubers 1439 Variant surface glycoprotein (VSG) 1744 Tumors 2668 Vasella-type reductive opening 363, 366, 969 Verbascose 70 Tunicates 1476 Verbascoside 2548 Turanose 71 Vibrio cholerae 2713 β-Turn 1778, 2087 Vicenistatin 543 Turn mimetics 997, 2085 Vilsmeier’s reagent 242 Twist-boat conformation 5, 468 Vinyl cuprate, magnesium-based 1926 Two-site insertion mechanism 1457 Vinyl glycosides 615, 624, 625 Tylosin 2611 active 621 Tyrosine sulfate 1844 Vinylations 889  2-Vinylfuran 940, 945 UDP-N-acetylglucosamine-4 epimerase 1369 Viscose 1494 UDP-Gal 1273 Viscose rayon process 1487, 1494, 1495 UDP-Glc 69, 1457 Vitamins 2628 glycoprotein glucosyltransferase 1786 VNTR 2647, 2650 UDP-GlcNAc 2157, 2168 Volemitol 1094 UDP-GlcNAc 2-epimerase/ManNAc Von Willebrand factor 2650 6-kinase 2135 Ugi reaction 1038, 2093 Waxy maize 73, 1426, 1440 UGM 1230 Weak interactions 2577, 2578 Ulose oximes, reduction 256 Weinreb amide 894, 904 Ultracentrifugation 2454 Welan 84, 1528 Undecaprenyl phosphate Western analysis 2180 in peptidoglycan biosynthesis 1545 Wheat amylose 1441 Unit cell 1479–1482 Whiskers 1492 Unsaturated sugars 344 Wilkinson catalyst 778 as chirons 344 Wittig olefination 2028 classification of 344 Wittig reaction 197, 199, 312, 358, 366, 889, 898 non-natural 344 intramolecular 1971 2874 I Index Wittig reagents 757, 761 Xylo-oligosaccharides 2363 [2,3]-Wittig rearrangement 1033 Xylorhamnan 502 Wittig–Horner–Emmons olefination 905 Xylose 65, 1127, 1128, 1130, 1982, 2275, 2286 Wood pulp 1487 D-Xylose-5-phosphate 66 Woodrosin I 1657 Xylosucrose 71, 1181 D-Xylulose-5-phosphate 66 X-ray crystallography 37 o-Xylylene ethers 119 X-ray diffraction patterns 1444 X-ray pattern, V-type 1447 Yeast 1862, 2147, 2388 Xanthan 84, 1415, 1518, 1520 Yield value 1519 Xanthate 1330 Ytterbium(III) Xanthation 1494 tris[bis(perfluorobutylsulfonyl)amide] 544 Xylanases 2365 Xylans 78, 502, 1425, 1489, 2363 Zaragozic acid 801 Xylaric acid 1100 Zemplén deacylation 131 Xylitol 87, 848, 898, 932, 1086 Zig-zag conformation 14 Xyloglucans 78, 1424, 1425, 2289 Zimmerman–Traxler 873 Xylomannans 1427 Zwitterion 2554