A-Transferase, 338 ABO Blood Group System, 330 and Cloning, 338
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Index A-transferase, 338 ALG9,165 ABO blood group system, 330 ALGlO,168 and cloning, 338 genetic basis of, 22 B-transferase, 338 activated oligosaccharides bacterial S-Iayers in glycopeptide synthesis, 466, 470 glycosylation in, 439 2-aminoethylphosphonate bacterial toxins in invertebrate glycoproteins, 420 and glycosylation, 413 anomer, 5 biological macromolecules formal defmition of, 6 the four groups of, 2 Hudson definition of, 6 bird's nest soup, 16 anomeric carbon blood group antigens, 22 in synthesis, 459 and cancer, 23 anomeric effect, 8 prognostic value of, 23 anomeric oxygen exchange reactions, blood typing, 22 460,461 ABO system of, 22 anomeric oxygen-retaining reactions, 460, Lewis system of, 22 464 Bombay blood group, 331, 336, 348 antennae Bombay phenotype, 22 definition of, 10 branch specificity, 93 J3-arabinofuranose in plants, 418 caeruloplasmin, 23 asialoglycoprotein receptor, 494 calnexin, 54, 182 asparagine-linked glycosylation genes calreticulin, 54, 182, 188 ALGI, 158 capillary electrophoresis, 457 ALG2,161 carbohydrate metabolism, 1, 17 ALG3,165 Carbohydrate-Deficient Glycoprotein ALG5,167 Syndrome (COGS) Type 1, 152 ALG6,168 Carbohydrate-Deficient Glycoprotein ALG7,155 Syndrome (COGS) Type II, 226 ALGB,168 500 Index Carbohydrates; See a/so oligosaccharides deoxymannoj irimycin, 191 as molecules with key biological deoxynojirimycin, 184 functions, 3 dietary sugars, 1 biology of, 2 disaccharides covalent attachment to protein, 17 structural determination of, 17 definition of, 4 DNA,1 in bacterial and viral infection, 4 dolichol, 149 in biology, re-evaluation of, 4 in the biosynthesis ofglycoproteins, in cancer and metastasis, 4 28 in signalling, 3 dolichol cycle, 99 optical rotation of: See mutarotation dolichylphospho-13-glucose (Dol-P-Glc) polymerisation of, 6 synthetase, 167 shorthand nomenclature of, 12 dolichylphospho-13-mannose (Dol-P· structure of, 5 Man) synthetase, 163 terminology of, 12 donor substrates castanospermine, 184 for glycosyltransferases, 88 chaperones, 182 drug targeting, 493 chemical synthesis ofglycosides, 459 13-elimination, 17 Chinese hamster ovary cells endoglycosidases /dlD mutant, 286 in structural determination of Lecl mutant, 217 oligosaccharides, 30 Lec4 mutant, 232 endomannosidase, 186 Lec9 mutant, 150 and glycoprotein folding, 55 LECII mutant, 364 enzymatic peptide ligation LEC 12 mutant, 364 in glycoside formation, 481 Lec15 mutant, 164 enzymatic synthesis Lec23 mutant, 185 automated, 479 Lec35 mutant, 164 ofglycosides, 475 chondroitin sulphate enzymes structural determination of, 17 Enzyme Commission designations of, cluster effects, 72 15 CMP-Neu5Ac epidermal growth factor-like domains biosynthesis, 374 glycosylation of, 308 hydroxylation, 375 epimer CMP-Neu5Gc, 375 definition of, 6 collagen erythropoietin glycosylation of, 315 as a glycodrug, 495 core structure O-linked glycosylation of, 283 definition of, 10 expression cloning, 32 CWH41,184 in S. cerevisiae, 430 Fischer projection, 6 cyclic acetals flipping carbohydrates as, 8 and the dolichol cycle, 100 cyclic hemiacetals dolichyl-oligosaccharide, 161 carbohydrates as, 5 fluorescence energy transfer experiments and glycoprotein folding, 57 deglycosylation Francis inhibitor, 21 methods for, 52 Index 501 a 1,3-fucose galactobiosides in plant glycoproteins, 414 as inhibitors ofbacterial al,6-fucosylation haemagglutination, 27 in invertebrates, 419, 420 galactofuranose in mammals, 236 in parasite glycoproteins, 424 fucosyltransferases galactomannans cloning of, 22 in S. pombe, 433 a 1,2-fucosyltransferase genes galactosaemia, 1 cloning of, 32 a-galactose human, 333 in mammals, 340 mouse, 337 in plants, 418 rabbit, 337 galactosyItransferases al,3-fucosyItransferases; See also and glycosaminoglycan biosynthesis, Fuc-TIll, etc. 312 in humans, 348 and N-linked glycosylation, 238 in invertebrates, 419, 420 and O-Iinked glycosylation, 296 in parasites, 426 al,3-galactosyltransferase (B in plants, 416 transferase), 23,338,341 a 1,3-fucosyltransferase genes human pseudogenes, 341 avian, 364 substrate specificity, 342 bovine, 365 pI,3-galactosyltransferases chimpanzee, 365 and mucin-type glycosylation, 295 He/icobacter pylori, 365 and N-Iinked glycosylation, 250 human pl,4-galactosyltransferase,238 FUT3,351 and poly-LacNAc biosynthesis, 369 FUT4,354 and rheumatoid arthritis, 248 FUT5,355 and a-lactalbumin, 239 FUT6,357 branch preference, 239 FUT7,359 cDNA cloning, 240 rodent cDNAs,32 FUT4,362 cell surface, 249 FUT7,363 cell surface localisation, 241 a 1,3/4-fucosyltransferase: See Fuc-TIll Golgi localisation, 245 a 1,4-fucosyltransferase in the synthesis oflactose, 32 in plants, 417 knock-out, 249 al,6-fucosyltransferase, core multiple genes, 243 mammalian, 236 post-translational modifications, 246 cDNA cloning, 237 substrate binding sites, 245 Fuc-TIII,350 substrate specificity, 239 Fuc-TIV, 354 galectins, 24 Fuc-TV,355 pI,4-GaINAc transferase Fuc-TVI,357 in invertebrates, 421 Fuc-TVII,359 in mammals, 385 furanose, 6 gangliosides,380 FUTI: See H (al,2-fucosyltransferase) Gaucher's disease, 480, 494 gene GlcNAc-l-phosphodiester a-N-acetyl- glucosaminidase galactobiose epitope, 23, 340 and lysosomal marker biosynthesis, and xenotransplantation, 342 391 502 Index GlcNAc-l-phosphotransferase glucosidase II and lysosomal marker biosynthesis, and glycoprotein folding, 54 389 glucosidases 1 and II, 184 GlcNAc-TI glucosylation, 413 cDNA cloning, 219 glucosyltransferase genomic localisation, 220 dolichyl-Iinked substrate, 168 Golgi localisation, 220 glycoprotein substrate, 189 in invertebrates, 419 f31,3-glucuronyltransferases in mammals, 217 and glycosaminoglycan biosynthesis, in plants, 416 312 knock-out, 221 and HNK-l epitope biosynthesis, 387 substrate specificity, 218 G1yCAM-l,366 G1cNAc-TIl, 419 biosynthesis of, 285, 362 cDNA cloning, 226 mucin-type oligosaccharides of, 360 in invertebrates, 419, 421 sulphation of, 300 in mammals, 225 glycation, 412 in plants, 416 and the Amadori rearrangement, 412 substrate specificity, 225 and the Maillard reaction, 412 GlcNAc-TIll, 227 glycoamidases and metastasis, 229 in structural determination of cDNA cloning, 228 oligosaccharides, 30 G1cNAc-TIV,230 glycobiology, 33 cDNA cloning, 230 coinage ofthe term, 2 G1cNAc-TV glycoconjugates and cancer, 31 and cancer, 30 and metastasis, 233 coinage ofthe term, 2 and the Warren-Glick phenomenon, definition of, 2 233 hierarchical classification of, 13 cDNA cloning, 232 glycodrugs, 494 genomic localisation, 233 glycoforms, 33, 457 substrate specificity, 231 impact on drug design, 34 GlcNAc-TVI,235 isolation of, 457 f31,3-GlcNAc transferase synthesis of, 457 and poly-LacNAc biosynthesis, 369 varying properties of, 34 core 3 glycogen and mucin-type glycosylation, 300 as a glycoprotein, 35 f31,4-GlcNAc transferase catabolism, 17 cloning ofthe invertebrate enzyme, glycohazards, 411 421 glycoimmunology,4 f31,6-G1cNAc transferase glycolipids, 17 and poly-LacNAc biosynthesis, 369 glycopathology, 4, 31 core 2 glycophorin, 21 and mucin-type glycosylation, 295 glycoprotein, 1 core 4 definition of, 13 and mucin-type glycosylation, 301 as a mixture ofglycoforms, 33 GLS2 glycosaminoglycans, 309 in S. cerevisiae, 430 glycoscience,4, 15 o-glucose glycosidase inhibitors, 181 structural determination of, 16 Index 503 glycosidases, 4, 33, 85 GPI membrane anchors and the cleavage ofglycosides, 89 biosynthesis, 124 endoglycosidases, 90 in parasites, 422 exoglycosidases, 90 glycoamidases, 90 H (al,2-fucosyltransferase) gene, 331 in glycoside fonnation, 479 cloning, 333 trans-glycosidases, 90 polymorphisms, 335 glycosides haemagluttination, 19 shorthand nomenclatures for, 8 Helicobacter pylori, 284, 352 synthesis of, 458; See also Chapter 9 al,3-fucosyltransferases of, 365 thennodynamic barrier to fonnation HEMPAS,223 of, 87 hepatic receptor protein, 24 glycosidic bonds: See glycosides J3-hexosaminidase glycosidic linkages: See glycosides in invertebrates, 419, 420 glycosyl acceptor, 8 in mammals, cytosolic, 307 in synthesis, 459 HNK-I epitope,387 glycosyl donor, 6 H-transferase (a1,2-fucosyltransferase), in synthesis, 459 334 glycosylamino acids Hudson's rule, 6 in glycopeptide synthesis, 466 violation of, 6 glycosylation human chorionic gonadotropin, 35 in insects, 418 hydrazinolysis, 29 in invertebrates, 418 hydroxylysine in mammals: See individual enzymes glycosylation of, 315 in parasites, 422 hypennannosylation in plants, 414 in yeast and fungi, 427 in snails, 421 in yeast and fungi, 427 I-cell disease, 390 glycosylation engineering, 482 immunogenic oligosaccharides, 411, 417 glycosylation mutants, 29 immunoglobulin G, 31 glycosylphosphatidylinositol membrane influenza virus, 19 anchors, 74 invariant region ofoligosaccharides: glycosyltransferases, 4, 33, 85 See core structure, definition of blood-group associated, 22 defective alleles, 22 Jaeken syndrome, 152 discovery of, 28 gene cloning, 32 heterologous expression of, 32 kifunensine, 192 in glycoside fonnation, 475 kin recognition in synthesis, 32 ofglycozymes, 91 purification of, 31 Koenigs-Knorr procedure, 461 structure/function relationships and, Kre2plMntip 87 in S. cerevisiae, 432, 436 transcriptional regulation of, 31 KRE5 glycotechnology, 4, 411 in S. cerevisiae, 428 glycotype, 33, 85 KTR2,432 glycozymes, 85 KTR3,432 Golgi retention signals, 91 KTR4,432 Go-NaGa,93 KTR5,433 KTR6,433 504 Index KTR7,433 mannosidase, ER, 190 cloning of, 193 LacdiNAc sequences, 121 a 1,2-mannosidase, 190 in invertebrate glycosylation, 419 in invertebrates, 419 in mammals, 385 in yeast, 430 LacNAc,120 p-mannosides a-lactalbumin,