GLYCOLIPIDS New Comprehensive Biochemistry Volume 10 General Editors A NEUBERGER London L.L.M van DEENEN Utrecht ELSEVIER AMSTERDAM NEW YORK OXFORD G1ycolipids Editor H WIEGANDT Marburg/ Lahn 1985 ELSEVIER AMSTERDAM NEW YORK.OXFORD 1985 Elsevier Science Publishers B.V (Biomedical Division) All rights reserved No part of this publication may be reproduced, stored in a retrieval system or transmitted in any form or by any means, electronic, mechanical, photocopying, recording or otherwise without the prior written permission of the publisher, Elsevier Science Publishers B.V (Biomedical Division), P.O Box 1527, lo00 BM Amsterdam, The Netherlands Special regulations for readers in the USA: This publication has been registered with the Copyright Clearance Center Inc (CCC), Salem, Massachusetts Information can be obtained from the CCC about conditions under which the photocopying of parts of this publication may be made in the U.S.A All other copyright questions, including photocopying outside of the U.S.A., should be referred to the publisher ISBN for the series: 0-444-80303-3 ISBN for the volume: 0-444-80595-8 Published by: Elsevier Science Publishers B.V (Biomedical Division) P.O Box 211 lo00 AE Amsterdam The Netherlands Sole distributors for the USA and Canada: Elsevier Science Publishing Company, Inc 52 Vanderbilt Avenue New York, NY 10017 U.S.A Library of Congress Cataloging in Publication Data Main entry under title: GIycolipids (New comprehensive biochemistry; v 10) Bibliography: p Includes index Glycolipids Wiegandt, H 11 Series [DNLM: Glycolipids W1 NE372F v 10/ QU 85 G56861 QD415.N48 vol 10 574.19’2 s [574.19’247] 84-21266 [QP752.G56] ISBN 0-444-80595-8 Printed in The Netherlands Preface Fundamental to all living cells is the utilization of membranes, that basically comprize of lipid as the main barrier to an aqueous environment Therefore, a multiplicity of regulated modulations of the interphase between lipid and water is necessary to enable the membrane to perform its specialized functions; amongst many others these include provisions for cell communications and membrane rearrangements The glycolipids, as judged by the ubiquity of their occurrence in all cells, and their special physicochemical properties as well as their strategic positioning (frequently at the outer cell surface membranes), appear to be molecules particularly well suited to serve as links at the lipid-water membrane interphase Indeed, glycolipids are enabled to mediate between the hydrophilic and the lipophilic environments because of their unique constitution, the molecular combination of a hydrophdic carbohydrate and a lipophilic aliphatic hydrocarbon chain residue Positioned in the lipid bilayer, the glycolipids can, with their lipid ‘tails’, dramatically influence the properties of biological membranes, as exemplified in the haloand thermophilic organisms In addition, many glycolipids carry very complex carbohydrates that may enable highly specialized interactions towards the aqueous environment The obvious multitude of modulatory requirements at the membrane interphase is possibly reflected by the diversity and variability of the structural constitutions of the glycolipids Still, most glycolipids can be classified into three major groups, and are distinguished by the molecular entity to which the carbohydrate moiety is directly linked These groups are: the sphingo-lipids, including their sialic acid-containing components, the gangliosides; and furthermore, the glycero- and isoprenol-glycolpids Whereas the functional significance of the isoprenol-glycolipids may reside in their ability to mediate the transport of carbohydrates through lipid membranes as part of the biosynthesis of glycoproteins, the sphmgo- and glyceroglycolipids appear to serve more directly as fundamental membrane constituents VI Glycolipids have received special attention in several areas of medical interest Besides their participation in the immunological expression of cells (they may be involved in storage diseases), they have been implicated to play an important role in the regulation of the social behavior of cells, including cancer, and some of them have been even found to be therapeutically useful agents in the treatment of neurological disorders, such as peripheral nerve injury and other peripheral as well as central neuropathies The advances in biochemical methodology in recent years has also considerably increased knowledge of the glycolipids; in fact, to such an extent that it is becoming difficult to find an easy access to all available information With the present volume, we have attempted to describe, the main groups, and to collate the present knowledge of the glycolipids This has been done, however, not only with the intention of reviewing the more recent advances, but also to allow for the interested nonspecialist reader to become introduced to the respective fields In addition, in accordance with the title of the New Comprehensive Biochemistry series, some attempt was made to make the present volume as comprehensive as seemed reasonable, in order to be useful as a reference source of the most relevant hitherto published data on glycolipids H Wiegandt Department of Biochemistry School of Medicine Philipps University Marburg an der Luhn F.R G Contents Preface by H Wiegandt V Chapter Glycosphingolipids, by A Makita and N Taniguchi I 3.4 High performance liquid chromatography 3.5 Determination of GSL constituents Introduction 3.2 Fractionation 3.7 3.5.2 Sphingoid bases Mass spectrometry of whole GSLs 3.11 Radiolabelling of GSLs pports and macromolecules 3.12 Covalent attachment of 3.13 Immunological procedu The lipophilic moiety of GSLs 4.1 Long-chain bases 5.1 Gala series 15 15 16 16 19 5.2.1 Glucosylceramide 5.2.2 Glucocerebroside-ester 5.2.3 Lactosylceramide 5.3 Globo and isoglobo series 5.3.1 Globotriaosylceramide 20 20 VlII 5.3.2 Globoisotriaosylceramide 5.3.3 Isoglobotetraosylceramide 5.4 Ganglio series 5.4.1 Gangliotriaosy 5.5.1 5.5.2 5.5.3 5.5.4 5.5.5 5.5.6 Lactotriaosylceramide Neolactotetraosylceramide , Lactotetraosylceramide 1V3-a-Galactosyl-neolactotet IV3-~-Galactosyl-neolactotetraosylceramide IV4-a-Galactosyl-neolactotetraosylceramide 5.5.9 Neolactodecaglycosylceramide 5.6.2 Lactosylceramide sulfate 5.6.3 Sulfated tri- and tetraglycosylceramides 5.7 Fucolipids 5.9.1 Phosphorus-freeglycosphingolipids 6.3 6.4 6.5 Biosynthesis of glucosylceramide Biosynthesis of di- and trihexosylceramides a and 8-N-Acetylgalactosaminyltransferasesinvolved in substance 6.9 Galactosylceramide sulfotransferase 7.1 lCeramidase , 7.1.7 a-Fucosidase 7.2.2 Activator protein for the hydrolysis of 8-glucosides 21 21 21 22 22 23 23 23 24 24 24 25 25 25 26 26 26 26 26 27 27 27 28 36 38 41 42 43 43 44 45 46 46 47 48 48 50 50 51 51 51 52 53 53 54 54 55 55 56 56 IX 7.2.3 Activator protein for the hydrolysis of ganglioside II'NeuAc-Gg,Cer 7.2.4 Activator for arylsulfatase A 7.2.5 Transfer proteins 7.3 Metabolic disorders of glycosphingol Glycosphingolipids in immunology 8.1 Human blood group systems 8.1.1 ABO system 8.1.2 Lewis system 8.1.3 lisystem , 8.1.4 P system 8.2 Heterophile antigen lycosphingolipids 8.3 Stage-specific embryonic antigens , and effects on the antigens of lectins and 8.4 GSL antigen marke differentiation inducers , 8.5 Antigenicity of simple glycosphingolipids and possible olvement of neutral and acidic GSLs in autoimmunization Glycosphingolipid changes in transformation and malignancy 9.1 Glycosphingolipid pattern and metabolism in transformed cells and their possible relationship to cell behaviors 9.2 Glycosphingolipid changes in tumor tissues and GSLs as possible tumor markers References , 56 57 57 51 59 60 60 62 63 65 67 68 69 12 73 13 77 82 Chapter G[ycoglycerolipids,by I Ishizuka and T Yamakawa , 101 Introduction Structure 3.1 Plant 3.1.1 Tissue distribution 3.1.3 Differentiation 3.2.5 Growth stage 3.3.2 Regional distribution 101 101 104 104 105 105 106 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Glycolipidr 00 (1985) WGDOOOSI 307 I985 Elsevier Science Publishers B V (Biomedical Division) Subject index AAG alkylacylglycerol 104 ABO blood group system 60 Acanthamoeba castellani 43 2-acetamid0-3.4-dihydroxy-5-caboxypiperidine 208 Acetobacter xylinum 267, 278 Acholeplasma 111, 175 granularum 118 laidlawii 106, 118, 139, 140, 179, 180 modicum 177 oxanthum 177 Activator protein 55 Acyl exchange 151 Adenohypophysis 227 ADHP, dihydroxyacetone phosphate pathway 127 ADP-ribosyltransferase 243 Adrenal chromaffin granules 227 Adrenal medulla 227 Aerobacler exopolysaccharide 276 Algae, blue-green 133 Alginic acid 279 Alk-1-enyl ether phospholipids 127 Alkenylacylglycerol synthesis 150 Alkylacyl GGroLs 121 Alteromonas rubescens 126 Alveolar membrane 147 Aminoalkylagarose 207 Amphomycin 282, 294 Amyloplasts 174 Amyotrophic lateral sclerosis 239 Anabaena variabilis 152, 154, 179 Anaeroplasma 111, 136 Anomeric configuration-chromium trioxide procedure 219 Antibiotic 24010 295 Anti-Gal2DAG 54 Anti-Gal a1-6GalS1-3DAG 177 Antigangliotetraosylceramide73 Antiglobopentaosylceramide(anti-IV’GalNAcaGb,Cer) 20 Antiglobotriaosylceramide 67 Antilactosylceramide 72 Antisulfo-GalAAG 178 Antisulfo-GalCer 178 Aplysia kurodai 43 Arabinose 42 Arabinosyl cytosine 121 Ara-CDP-DAG 121 Archaebacteria 112, 121, 125, 127, 134, 180 classification 125 Artemisia princeps 130 Arthrobacter 135, 136 Arthro series 42 Arylsulfatase 54 Arylsulfatase A (EC 3.1.6.1) 167 Aspergillus fumigatus 268 Aspergillus niger 43, 286 Asterina pectinifera 203 Atotobacter uinelandii 279 Bacillus, acidocaldarius 132, 136 cereus 131, 140, 294 licheniformis 278 308 megaterium 117, 175 subtilis 136, 137, 175, 179, 182 phosphate limiting medium 181 Bacitracin 291, 297 Bacteria, gram-positive, chemical taxoncm y 102 Bacteriochlorophyll 134 Bacterium licheniformis 150 B-active glycolipid, rabbit 25 Bactoprenol 263 Bacterial antigen 176 Betulaprenol 263 Betula uerrucosa 263 Bial's reagent 199 Bifidobacterium 137 153, 154, 158 Blastocladiella emersonii 133 Blastocysts, mouse 68 Blastocysts, murine 68 Blood group A 59 Blood group B 50 Blood group systems 60 Botulinus toxin 241 Callose 288 Cancer-related glycosphingolipids 78 Carboxypeptidase 286 Carcinoma cells, embryonal, mouse 69 Carcinoscorpin 241 Cardiolipid 121, 127 Cardiolipin, biosynthesis 153 Cardiolipin, glucosylated 117 Cell aging 235 Cellobiosyl diphospholipid 278 Ceramidase, 51 Ceramide 200 Ceramide, alteration 205 Ceramide, biosynthesis 111 Ceramide phosphorylglycerol 106 Cerebroside 202 Cerebroside sulfate 27 Charonia lampas 167 Chicken egg yolk 202 Chicken embryonic liver 202 Chlamydomonas reinhardtii 134 Chlorellq pyrenoidosa 153, 156 uulgaris 130, 151, 162 Chlorobium 134 Chloroplast membrane 134 Chloroplasts 133 Chlorosulfolipids 183 Chlorpromazine 245 Cholera toxin 237, 243 Chromium trioxide oxidation I3C-NMR spectroscopy 13 Colanic acid 276 Colchiceine 245 Colominic acid 278 Compactin 297 Concanavalin A 178 Creutzfeld-Jacob subacute spongiform encephalopathy 234 Cyanidium 179 Cyanobacterium 106 Cyclohexyl fatty acids 125 11-Cyclohexylundecanoic acid 132 13-Cyclohexyltridecanoic acid 132 Cyclopropane acids 125 Cyclopropane synthetase 152 Cytolipin H 72 Cytolipin K 21 Cytolipin S 23, 70 DAG, diacylglycerol 104 2,3-Dehydro-2-deoxy-N-acetylneuraminicacid 208 2-Deoxy-2-fluoroglucose 294 2-Deoxy-2-fluoroma~ose294 2-Deoxyglucose 294 2-Deoxyglucosyl phosphodolichol294 Detergents, spermicidal activity 178 Deuterostomia 224 Diacylglycerol synthesis 150 Diatoms 133 Dibi-phytanyl-glycerylether 127 Dibutyryl-CAMP 236 Dichloro-dicyano-benzoquinone206 Dictyostelium discoideum 43 Differentiation, immune cell 71 Digalactosyl ceramide 46 Digalactosyl diacylglycerol 101 Dihydrosphingosine 15 3,4-Dihydroxy-butyl-l-pyrophosphate159 Dimannosyl ceramide 41 Dinitrophenylhydrazine 208 Di-0-akylGro 121 Di-0-phytanylether 127 Diphosphopolyprenols 291 Direct inlet mass spectrometry Di trans-polycis-prenols, bacteria 263 Diumycin 295 Docosapentaenoic acid 147 Dolichol kinase 267 Dolichols 262, 263 Dunaliella 182 309 Ehrlichs reagent 199 Eicosasphingenine 15 Electron impact mass spectrometry Embryonal carcinoma cells, murine 68 Embryonic stage specific substances 68 Embryos, mouse 69, 165 Endo-/%galactosidase7, 95 Epididymis 146 Erythrocytes, human 203, 204 Erythrocytes, mouse 202 Escherichia coli, exopolysaccharide 276 toxin 242 Euglena gracilis 162 Exoglycosidases7 Experimental allergic encephalomyelitis 239 Fabry’s disease 21, 54 Farnesyl pyrophosphate 270 Fast atom bombardment mass spectrometry 10 Fatty acid, composition, age dependence 140 Fatty acid, distribution, GalDAG in plant 130 Fatty acid methyl esters Fatty acids 16 cyclopropanisation 152 distribution in bacteria 130 positional distribution 129 short chain 236 6-Fatty acyl-glucosylceramide13 Fibronectin 244, 292 Ficaprenol263, 279 Ficus elastica 263 Field desorption mass spectrometry 10 Flavobacterium stearothermophilus 136 Flavomycin 295 Fluorescence recovery after photobleaching 224 Folch partition 4, 210 Forssman antigen, antigenic determinant 68 Forssman-antigenic F-polysaccharide, pneumococcus 119 F-polysaccharide 178 FSH, follitropin 146 Fucolipids 28 Fucosamin 106 Fucosidase 7, 55 Fucosidosis 55 Fucosyltransferase 48 Fungi 133 Galabiaosylceramide 19 Galactocerebroside esters 19 Galactolipid, distribution 132 Galactose oxidase 14, 208, 236 Galactosidase 7, 52, 54, 55 Galactosylceramide 16 biosynthesis 45 sulfate 27 sulfotransferase 50 Galactosyldiacylglycerol101 Galactosyl glycerolipids 103 Galactosyl lactoneotetraosyl-ceramide65 Galactosyl phosphoretinol290 Galactosyltransferase 50 Galacturonic acid 106 Gala series 16 GalMAG 174 Ganglioside, sialidase resistance 210 Ganghopentaose 203, 205 Gangho series 23,200, 202 Ganglioside, aggregation properties 220 alteration, chemical, enzymatic 205 albumin complexes 241 analogue, lateral diffusion 224 analogues 207 electron spin resonance labelled 236 biodegradation 230 biosynthesis 229 brain, adaptive divergence 148 poikilotherms 225 cation binding 224 cell growth inhibition by 237 cell uptake 236 cellular localisation 228 central nervous system 226 changes in disease 234 chemical constitution 200 chemistry 200 colon carcinoma 238 critical micellar concentration 220 developmental alterations 232 dipole moment 221 distribution 224-226 erythrocytes 224, 225 frog, fat body 203 G l a d 200 Glac2 203 hydrazinolysis,N-deacetylation-reacetylation 210 hydrogenation 207 localisation 210 mapping 211 melanoma, human 238 molecular packing 219 neurohypophysis 202 nomenclature 205 310 N-tnfluoroacetyl-neuraminyl208 oxidative cleavage 206 peripheral nerve 227 phospholipid, match of dipole vectors 220 physicochemical characteristics 219 rat, intestinal nonepithelial tissue 205 retina 203, 228 skeletal muscle, chicken 205 starfish 225 surface requirements 221 syndrome 73 temperature adaptive changes 234 visual system 227 Gangliosidoses 230 Gangliotetraose, 203, 205 Ganghotetraosylceramide23, 70, 229, 240 Ganghotetraosylceramide-disulfate28 Ganghotriaose 32, 82, 203, 205 Gangliotriaosylceramide23, 230 Ganghotriaosylceramide-did fate 28 Ganghotriaosylceramide-sulfate28 Gas chromatographic techniques 211 Gas chromatography carbohydrates Gastrointestinal mucosae 63 Gaucber's disease 20, 53, 56, 57, 232 Gentiobiose 177 Gentiobiosyl-DAG 176 G,,,l 202 GGroLs, animal 106 chemical synthesis 112 glycoglycerolipids 104, 121 plant 106 G lac 202 Glc-DAG 154 Glc-Glc-DAG 154 GlcU-DAG 181 GlcU glucuronic acid 154 Globoisotriaosylceramide21 Globopentaose 205 Globopentaosylcerarnide9 23 Globo series 20 47, 78 200 Globoside 3, 21, 47, 69 Globoside acid sepharose 47 Globotetraosylceramide11, 65, 69 Globotriaosylceramide20, 46,65 Glucocerebroside-ester20 Glucosaminyl-phosphatidylglycerol102 Glucosidase 7, 53 Glucosylceramide20 Glucosylceramidebiosynthesis 46 Glucosyl-diacylglycerol 102 Glucosyl-glycerolipids103 Glucosyl monophosphopolyprenol 279 Glucuronic acid 42 289 /3-Glucuronyl-4,N-acetylglucosaminyl diphosphodolichol 289 Glucuronylceramide 41 Glycerol sn-2.3 127 Glycerophospho-GGroLs118 Glycerophosphoglycoglycerolipid102 Glycoglycerophospholipids,mycobacteria 117 Glycolipid acid 14 Glycophorin 60 Glycosphingolipid,non-vertebrate 38 biodegradation 51 biosynthesis 43 cell density dependence 77 changes 73 classification constituents extraction hydrolase activator protein 231 in malignancy 73 in transformed cells 73 isolation mass spectrometry 219 nomenclature preparation series storage diseases 59 tumor markers 77 Glycosyl phosphopolyprenols 261 Glycosyl transfer 273 Glycosyltransferases,cell surface 77 GM, gangliosidosis 52 G M2 gangliosidosis 56 Gonadoliberin 146 Gram-positive eubacteria 135 Graves disease 73 Gro, glycerol 105 GroP-GGroL, glycerophosphoglycoglycerolipid 105 GroP, glycerophosphaie 106 growth cycle of cell, arrest at G1 phase 293 Gle,l 202 Gl,il 202 Guluronic acid 279 Halobacteria 127 Halobacterium,cutirubrum 174, 182 halobium 182 rnarismortui 156, 174 salinarium 278, 291 31 Halophilic bacteria, salt dependence 182 Hanganutziu-Deicher (H-D)antibodies 68 Hematoside 202 Heparan sulfate 289 Hexosaminidase A 231 Hexosaminidase activator protein 241 Hexosaminidase B 231 Hexosaminidase S 231 High performance liquid chromatography HMGCoA, hydroxy-methyl-glutarylcoenzyme A 268 HMGCoA reductase 295, 296 Hordeum 134, 182 Horse radish peroxidase 14 Hydroxy acid esters 25-Hydroxycholesterin 295 Hydroxy fatty acids 13, 16 Hydroxysphinganine 15 Iatrobeads Ii blood group system 63 Impariens balsamia 182 Infrared spectroscopy 13 lnositolphosphoceramides 42 Interferone-ganglioside interaction 243 lnvertase 286 Isogala series 42 Isoglobopentaose 205 Isoglobo series 20 lsomaltose 112, 147 Isopentenyl pyrophosphatase 269 Isopentenyl pyrophosphate 270 Keto-ganglioside 206 Klebsiella aerogenes capsule 275 Kojibiose 177 KojibiosylDAG 118, 178 Krabbe's disease 52 Lactalbumin 46 Lacrobacillus 121, 136, 263 casei 106 130, 135, 136, 140, 269 fermenri 138 group A, F antigens 176 plantarum 267, 268, 271 Lacto-klado-hexaose 204 Lactoneohexaosylceramide 204 Lactoneotetraosylceramide24 Lacto-nor-hexaose 204 Lactose 46 Lacto series 24, 200 Lactosylceramide 20, 46 Lactosylceramide sulfate 27 Lactotetraose 204 Lactotetraosylceramide 25 Lactotriaosylceramide 24 Lactotriaosylceramide sulfate 27 Lands cycle 151 Lectins 178 Lewis blood group system 62 LH, lutropin 140 LH-RH, gonadoliberin 146 Limulin 241 Lipid bilayer 180 Lipid metabolism of bacteria, reviews 103 Lipomannan 110, 138 binding of Mgz+ 181 Lipophosphonoglycan 43 Lipoproteins, high-, low-density 63 Lipoteichoic acid 40,118 119, 127,137, 138, 158, 159 carrier 119 extracellular, deacetylated 140 mitogenicity 175 stimulation of osteolysis 175 T-cell dependent immunogen 176 Lipoteichoic polyglycerophosphogIycoglycerolipid 102 binding to eukaryotic cells and complements 175 Lnn, linolenic acid 130 Low density lipoprotein cholesterol 296 LPS, lipopolysaccharide 176 LTA, lipoteichoic acid 118 LTC, lipoteichoic acid carrier 119 Lung alveoli 129 Lupus erythematodes 240 Lutropin 140 Lymphokines 237 Lysoganglioside 200 Lysoglycolipids 59 Lysoseminolipid 172 Macroglycolipids 36 Macrophage activation factor (MAF) 244 MAG, monoacylglycerol 105 Maize leaves 134 Malabiosylceramide 41 Membrane fusion 221 Man-inositol-P-DAG 153 Man-Man-DAG 154 Man-myo-inositol-phosphate117 Mannoglucosylceramide 106 Mannoheptose 106 312 Mannosylceramide 41 Mannosyl monophosphopolypreno1279 Mannosyl-N, N-diacetylchitobiosyl-diphosphodolichol 291 Mannosylphosphatidylinositol 101 Mannosyl phosphodolichol282 Mannosyl phosphoretinol290 Mannuronic acid 279 Man-p-undecaprenol 118 Marine diatoms 134 Mass spectrometry 9, 211 Meconium 25, 29 human 78 Megaloglycolipids 36 Meningococcal C-polysaccharide 176 Meningococcus 121 Metachromatic leukodystrophy 27, 57, 167 Methanospirillum hungutei 136 Methioninehydrazide 208 Methylation analysis Mevalonic acid as growth factor 268 Micelles 220 Microbacterium lacfinum 136 Micrococci 136 Micrococcaceae 125 Micrococcus, lureus 110, 118, 138 154, 157, 160 lysodeikticus 274 lysosuperificus 291 uarians 160 Migration inhibition factor (MIF) 244 Mollu series 42 Monoclonal antibodies 15 71 Monoclonal antibodies, tumor-associated 72 Monophosphopolyprenols 266 Monosaccharide transfer 273 Monosialo-gangliotetraose243 Morulae mouse, 69 Multiple sclerosis 177 234, 240 Mung bean 129,135 Mycobacteria 127 Myco&acierium smegmaris 294 Mycoplasma, 134, 139 180 ucidocaldarius 173 mycoides 106, 139 neurolyticum 139 176, 177 pneumonioe 139 Mycospocidin 294 Myelination 142 Myelination marker 144 Myelin oligodendral 226 Myeloid leukemia cells, mouse 71 Myoblasts 221 Myotubes 221 N-Acetylgalactosaminetransferase236 a-N-Acetylgalactosaminidase55, 7, 54 IV 3-N-Acetylgalactosaminyl-~-neolactotetraosylceramide 67 N- Acetylgalactosaminyltransferase 47, 48 a-N-Acetylgalactosaminyltransferases (A enzyme) 62 N-Acetylglucosaminyl diphosphopolyprenol 279 P-N-Acetylhexosaminidase7, 53 N-Acetylmuramic acid 277 natural killer (NK) cells 70 Neisseria meningitidis 148 Neogala series 42 Neolacto series 24 Neolactotetraosylceramide 46 Neolactotetraosylceramide sulfate 27 Neurite outgrowth 227 Neuroblastoma 227 Neurohypophysis 227 Neuronal perikaryon membrane 210 Neurospora crassa 43 N-glycolyl-neuraminic acid 68, 241 N-glycosylation, plants 286 proteins 279, 285 stimulation by oestrogen 297 NIL cells 77 Nifrschia alba, marine diatom 125 N, N-diacetylchitobiose 38 N N’-diacetylchitobiosyl diphosphodolichol 281, 283 NS-4 cell surface antigen 177 0-antigen determination 275 0-glucosylation, proteins 288 0-glycosylation, plants 287 proteins 279 Oligosaccharide transfer 273 0-mannosylation, proteins 280 Osmium tetroxide-periodate oxidation 14 Ozonolysis 14 PI-active trisaccharide 65 P,-glycolipid 26 P-antigen 22, 60 Paragloboside 24 Paul Bunell antibodies 68 Penicillin 140 Pen tasialo-gangliotetraosylceramide 204 Peptidoglycan 273 277, 278 Perikarya, oligodendroglial 226 Periodate oxidation Permethylation 211 Phosphatidyl-GGroLs 102, 118 313 Phosphatidyl-glucose 118 Phosphatidylinositol mannoside 127, 153 Phosphobactoprenol297 phosphodolichol cycle 281 block 294 distribution 284 enzymes, topological orientation 285 Phosphoglycosphmgolipids38, 42 Phospholipid, hydration capacities 181 Phospholipids, hydration 181 Phosphonoglycosphingolipids 38, 43 Phosphopolycis-prenol, nomenclature 271 Phosphopolycis-prenols, preparative separaticJn 266 Phosphopolyprenol phosphatases 295 Phosphopolyprenols, biosynthesis, control 295 Phosphoretinol 289 Phytoglycolipid 42 Phytosphingosine 15, 16, 42 P k-antigen 60 P k-erythrocytes 65 Plasmenic acid 121 Pneumococcal polysaccharide type XIV 25 Pneumococcus 106 autolysin 178 type XIV 154, 160 Polycis-isoprenoid alcohols, chemistry 262 Polycis-prenols, biosynthesis 268 metabolism 265 Polyclonal antibodies 71 Polymannan 286 Polyprenol kinase 267, 295 Poly(ribitol-P) polymerase 159, 160 Polysialosyl-phosphatidic acid 148, 176 cis-Prenyl transferase 269 Procollagen 293 Prostaglandin E, 236 Protein kinase C 236 Proton NMR spectroscopy 11, 219 Protostomia 224 Proioiheca zopJi 268, 288 Pseudomonas diminuta 137, 153, 154, 158 halosaccharolytica 182 ooalis 117 rubescens 112 oesicularis 137 Ptd-GGroL phosphatidylglycoglycerolipid 105 PtdGro, phosphatidylglycerol 117 Pyrophosphoundecaprenol synthetase 271 Q, quinovose 106 Radiolabelling 14 Reductamination 207 Retinol phosphate 280 Rhamnose 106 Rhizopus delemar 131 Rice bran 106, 133 Ricinus communis lectin (RCA1) 241 Ristocetin 295 Saccharomyces cereoisiae 133, 286 Saliva, human 129 Salmonella, exopolysaccharide 276 newington 268 0-antigen determinants 275, 276 Sandhoff-Jatzkewitzdisease 23, 53 Schizophrenia 239 Sea wasp toxin 242 Secondary (or sputtered ion) mass spectrometry 10 Seminal tubules 145 Seminolipid 103, 112, 129, 141, 144, 165, 167, 172 antibody 178 critical micellar concentration 172 synthesis, glycerylether backbone 151 Seminoma 146 Sendai virus 237 Serotonin binding protein 46, 245 Serotonin, binding of gangliosides to 46 245 Serum sickness 239 2-0-Sesterpanyl-30-phytanyl-sn-Gro 127 Showdomycin 294 Sialic acid 199 evolution 148 lactone formation 201 periodate oxidation 208 Sialidase 76, 208 Sialidases, specificities 209 Sialyltransferase CMP-sialic acid; lactosylceramide 236 Siastatin 208 Smith periodate degradation 211 Solvolysis, sulfate esters 117 Spermatocytes 103, 106, 112 145, 156, 165 Spermatogonia 146 Spermatozoa, epididymal, bovine 129 Sperm, capacitation 175 guinea pig, autoantibody 178 Sphinganine 15 Sphingoid bases Sphingoid biosynthesis 44 Sphingoid composition, gangliosides 21 Sphingolipidoses, characteristics 58 Spinal cord 111 129 314 SQ-DAG, 6-sulfoquinovosyl-diacylglycerol 105 Squalene 269 SSEA-1, stage specific embryonic antigen 27, 69 SSEA-3, stage specific embryonic antigen-3 69 Staphylococcus, aurew 36, 137, 158, 159, 174, 182, 263, 267, 273 epidermis 126, 131, 148, 183 faecalis 131, 132 a-toxin 242 starfish 201 stereospecific numbering 105 Streptococci, group A 169 Streptococci, group B 117, 131, 136 Streptococci, group D 136, 176 Streptococci, group N 136 Streptococcus, faecium 106 118, 121, 136, 139, 140, 154, 157, 158, 160 169 group N antigen 176 hemolyticus 117 118, 126 135, 136 luctis 119, 130, 159 mutans 138, 176 parahemolyticus 242 pyrogenes 137, 174 pyrogenes, group A 119 sanguinis 158 showdensis 294 zymogenes 178 Streptovirudin 294 Sulfatidosis 57, 167 Sulfatid, sulfo-GalCer, immunogenicity 178 Sulfoglycolipids, reviews 117 Sulfoglycolipids specific assay, azure A complexing 112 Sulfo-LacCer 146 Sulfolipase 168 Sulfolobus 127 Sulfoquinovosyl-diacylglycerol101, 168 Sulfotransferase 155 Sulphatide 13 Sulphoglycosphingolipids13 Synaptogenesis 233 Synaptosomes 210 Systemic lupus erythematodes 73 Tay-Sachs disease 23, 53, 231 Teichoic acid 102, 178, 181 Teichoic acid, formation 277 Teichuronic acid 181, 278 Teratocarcinoma cells, mouse 68, 69 Testis, boar 112 human 106 rat 112 Tetanus toxin 241 Thermoacidophilic bacterium 125 Thermoplmma ucidophilum 106, 127, 139 Thermus thermophiium 106, 180 Thin layer chromatography 21 Thylakoid membrane, phase transition temperature 179 Thylakoids 134, 160 Thymus T-cells, mouse 70 Thyroid hormone 144 Thyroid stimulating hormone 242 Thyrotropin 242 Trarrsacylase 267 Transfer protein 55 Transphosphatidylation 153, 158 Transprenyl-transferase 27, 137 Trimannosylceramide 41 Tri trans-pol yeis-prenols 263 Trophoblast cells 292 tuberculosis 101 d-Tubocurarine 43 224 245 Tumor-associated antigens 63 Tunicamycin 281, 286, 291 Undecaprenol263 Vaccenic acid 174 Vancomycin 295 Virus receptor 46 Wheat germ agglutinin 241 Xylose 106 Xylosyl monophosphodolichol 289 .. .GLYCOLIPIDS New Comprehensive Biochemistry Volume 10 General Editors A NEUBERGER London L.L.M van DEENEN Utrecht ELSEVIER AMSTERDAM NEW YORK OXFORD G1ycolipids Editor... Avenue New York, NY 10017 U.S.A Library of Congress Cataloging in Publication Data Main entry under title: GIycolipids (New comprehensive biochemistry; v 10) Bibliography: p Includes index Glycolipids. .. fields In addition, in accordance with the title of the New Comprehensive Biochemistry series, some attempt was made to make the present volume as comprehensive as seemed reasonable, in order to be