Neoglycoconjugates Part A: Synthesis

358 Pages·1994·5.958 MB·English

by  Y.C. Lee, Reiko T. Lee (Eds.)

Contributors to Volume 242
elcitrA srebmun era ni sesehtnerap gniwollof eht seman of .srotubirtnoc
snoitailiffA listed era Lnerruc
TOSHIHIRO AKAIKE (21), Faculty of Bio- T. FEIZI (19), Glycoconjugates Section,
science and Technology, Tokyo lnstitute of MRC Clinical Research Centre, Harrow,
Technology, Yokohama 227, Japan Middlesex HA1 3UK, United Kingdom
F. O. ANDERSSON (18, 25), Department of TSUYOSHI FUJIWARA (3), Institutefi)r Natu-
Chemistry, University of Ottawa, Ottawa, ral Science, Nara, Japan
Ontario, Canada KIN 6N5 TETSUYA FURUIKE (22), Division of Ecolog-
SABINE ANDRI~ (4), lnstitutfiir Physiologis- ical Science, Graduate School of Environ-
che Chemie der Universitgit, D-80539 mental Earth Science, Hokkaido Univer-
Miinchen, Germany sity, Sapporo 060, Japan
SIVASUBRAMANIAN ARAVIND (27), Depart- HANS-JOACHIM GABIUS (4, 6), lnstitut fiir
ment of Chemistry, University of Ottawa, Physiologische Chemie, Ludwig-Maximi-
Ottawa, Ontario, Canada KIN 6N5 lians-Universitdit, D-80539 Miinchen,
JOHN W. BAYNES (1), Department of Chem- Germany
istry and Biochemistry, School of Medi- SIGRUN GABIUS (4), lnstitutfiir Physiologis-
cine, University, of South Carolina, -oC che Chemie der Universitdit, D-80539
lumbia, South Carolina 80292 Miinchen, Germany
PATRICK J. BRENNAN (3), Department of IRWIN J. GOLDSTEIN (10, 11), Department
Microbiology, Colorado State University, of Biological Chemistry, University ~
Fort Collins, Colorado 32508 Michigan, Ann Arbor, Michigan 90184
DELPHI CHATTERJEE (3), Department of Mi- AKIRA HASEGAWA (15, 16, 17), Department
crobiology, Colorado State University, of Applied Bioorganic Chemistry, Gzfu
Fort Collins, Colorado 32508 University, Gifu 501-11, Japan
R. A. CHILDS (19), Glycoconjugates Sec- KENICHI HATANAKA (23), Faculty of Bio-
tion, MRC Clinical Research Centre, science and Biotechnology, To~yo In-
Harrow, Middlesex HA1 3UK, United stitute of Technology, Yokohama 227,
Kingdom Japan
SANG-NAE CHO (3), Department of Microbi- COLLEEN E. HAYES (10), Department of
ology, Yonsei University College of Medi- Biochemistry, University of Wisconsin-
cine, Seoal, Korea Madison, Madison Wisconsin 60735
~IRDNA DANGUY (4), Laboratoire de Biolo- MISAO HIROTO (7), Human Science and
gie Animale et Histologie Comparde, -nU Technology Center, Department of Mate-
iversite Libre ed Bruxelles, D-I050 Brux- rials Science and Technology, Toin Uni-
elles, Belgium versity of Yokohama, Yokohama 225, Ja-
STEPHEN P. DOUGLAS (26), Department of pan
Molecular and Medical Genetics, Protein YuJI INADA (7), Human Science and Tech-
Engineering Network of Centres of Excel- nology Center, Department of Materials
lence, University of Toronto, Toronto, Science and Technology, Toin University
Ontario, Canada M58 IA8 of Yokohama, Yokohama 225, Japan
HEINZ EGGE (13), lnstitut fiir Physiologis- HIDEHARU 1SHIDA (17), Department of Ap-
the Chemie der Universitiit Bonn, -D plied Bioorganic Chemistry, Gifu Univer-
51135 Bonn, Germany sity, Gifu 501-11. Japan
ix
X CONTRIBUTORS TO VOLUME 242
ELISABET KALLIN (12, 20), lsoSep AB, S- OKAYA AMIHSUSTAM (8), Human Science
641 36 Tullinge, Sweden and Technology Center, Department of
KLAUS KAYSER (4), Abteilung Pathologie, Materials Science and Technology, Toin
Thoraxklinik, D-69126 Heidelberg, Ger- University of Yokohama, Yokohama 225,
many Japan
OTOKAM KISO (15, ,61 17), Department of S. J. MEUNIER (8), Department of Chemis-
Applied Bioorganic Chemistry, Gifu Uni- try, University of Ottawa, Ottawa, On-
versity, Gifu 501-11, Japan tario, Canada KIN 6N5
OYIKUZAK IHSAYABOK (21), Faculty of Ag-
IKUYORIH NISHIMURA (7), Human Science
riculture, Nogaya University, Chikusa,
and Technology Center, Department of
Nagoya 464-01, Japan
Materials Science and Technology, Toin
OTOKAM KODAMA (6), National Institute
University of Yokohama, Yokohama 225,
for Advanced Interdisciplinary Research,
Japan
Bionic Design Research Group, lbaraki
305, Japan SHIN-ICHIRO NISHIMURA (22), Division of
Biological Science, Graduate School of
HOY KODERA (7), Human Science and
Science, Hokkaido University, Sapporo
Technology Center, Department of Mate-
rials Science and Technology, Toin Uni- 060, Japan
versity of Yokohama, Yokohama 225, Ja-
WILLIAM K. C. PARK (27), Department of
pan
Chemistry, University of Ottawa, Ottawa,
JIRI J. YKSNIPERK (26), Department of Mo- Ontario, Canada KIN 6N5
lecular and Medical Genetics, Protein En-
gineering Network of Centres of Excel- GOTTFRIED POHLENTZ (13), Institut fiir
lence, University of Toronto, Toronto, Physiologische Chemie, der Universitiit
Ontario, Canada M58 1A8 Bonn, D-53113 Bonn, Germany
C. A. LAFERRI~RE (8, 9, 25), Department of LYREHC M. REICHERT (10), Department of
Chemistry, University of Ottawa, Ottawa, Biological Chemistry, University of Mich-
Ontario, Canada K1N 6N5 igan, Ann Arbor, Michigan 48109
Su-CHEN LI (14), Department of Biochem-
NYLECOJ RENAUD (27), Department of
istry, Tulane University, School of Medi-
Chemistry, University of Ottawa, Ottawa,
cine, New Orleans, Lousiana 21107
Ontario, Canada KIN 6N5
Yu-TEH LI (14), Department of Biochemis-
try, Tulane University, School of Medi- A. AKSWONAMOR (8, 18, 24, 27), Depart-
cine, New Orleans, Louisiana 21107 ment of Chemistry, University of Ottawa,
Ottawa, Ontario, Canada KIN 6N5
T. JUHANI LINNA (5), Syntex Development
Research, Syntex (USA) Inc., Palo Alto,
R. RoY (8, 9, ,81 24, 25, 27), Department of
California 30349
Chemistry, University of Ottawa, Ottawa,
NEGROJ NERGNNOL (11), Pro Gene AB, Up- Ontario, Canada KIN 6N5
psala, Sweden
MAINAMARBUS SABESAN (5), Central Sci-
JAMES A. MAHONEY (2), Departments of
ence and Engineering, DuPont Company,
Pharmacology and Molecular Sciences,
Wilmington, Delaware 08891
The Johns Hopkins University School of
Medicine, Baltimore, Maryland 50212 DLANOR L. SCHNAAR (2), Departments of
KoJI AKOUSTAM (22), Division of Biological Pharmacology and Neuroscience, The
Science, Graduate School of Science, Johns Hopkins University School of Med-
Hokkaido University, Sapporo 060, Japan icine, Baltimore, Maryland 50212
CONTRIBUTORS TO VOLUME 242 xi
SUZANNE R. THORPE (1), Department of DENNIS M. WHITFIELD (26), Department f~e
Chemistry and Biochemistry, University Molecular and Medical Genetics, Protein
of South Carolina, Columbia, South Car- Engineering Network of Centres of Excel-
olina 80292 lence, University of Toronto, Toronto,
F. D. TROI'PER (8, 24), Department of Ontario, Canada M58 IA8
Chemistry, University of Ottawa, Ottawa,
Ontario, Canada KIN 6N5 NOBORU YAMAZAK1 (6), National Institute
TAICm UsuI (21), Faculty of Agriculture, of Materials and Chemical Research,
Shizuoka University, Ohya, Shizuoka ,638 Functional Molecules Laboratoo,,
Japan Ibaraki 305, Japan
Preface
Rising interest in glycobiology in recent years has led to similar inter-
est in neoglycoconjugates, a term given to carbohydrates conjugated to a
variety of materials, including proteins, lipids, and synthetic polymers.
Carbohydrates to be conjugated can be synthetically obtained or isolated
from natural products. Such neoglycoconjugates are useful tools in a wide
area of disciplines, ranging from clinical medicine to synthetic chemistry.
They serve as a chemomimetic of natural glycoconjugates with well-
defined structure and provide certain advantages over natural glycocon-
jugates.
Methods ni Enzymology Volumes 242 and 742 contain many practical
methods on how to prepare and use neoglycoconjugates, which have been
contributed by a group of international experts. This Volume (242) deals
with synthesis and Volume 742 with biomedical applications. Readers
should peruse all sections or utilize the indexes, since many chapters
contain both preparation and application.
We were pleased to be able to develop these volumes in the Methods
ni Enzymology series which complement our treatise "Neoglycoconju-
gates: Preparation and Applications" (1994, Academic Press).
Y. C. LEE
OKIER T. LEE
iiix
METHODS IN ENZYMOLOGY
EMULOV I. Preparation and Assay of Enzymes
Edited yb SIDNEY P. COLOWICK DNA NATHAN O. KAPLAN
EMULOV II. Preparation and Assay of Enzymes
Edited by SIDNEY P. COLOWICK DNA NATHAN O. KAPLAN
EMULOV III. Preparation and Assay of Substrates
Edited by SIDNEY P. COLOWICK DNA NATHAN 0. KAPLAN
EMULOV IV. Special Techniques for the Enzymologist
Edited yb SIDNEY P. COLOWlCK DNA NATHAN O. KAPLAN
EMULOV V. Preparation and Assay of Enzymes
Edited yb SIDNEY P. COLOWICK DNA NATHAN O. KAPLAN
EMULOV VI. Preparation and Assay of Enzymes (Continued)
Preparation and Assay of Substrates
Special Techniques
Edited yb SIDNEY P. COLOWICK DNA NATHAN O. KAPLAN
EMULOV VII. Cumulative Subject Index
Edited yb SIDNEY P. COLOWICK DNA NATHAN O. KAPLAN
EMULOV VIII. Complex Carbohydrates
Edited by ELIZABETH F. NEUFELD DNA VICTOR GRUBSNIG
VOLUME IX. Carbohydrate Metabolism
Edited yb WILLIS A. WOOD
EMULOV X. Oxidation and Phosphorylation
Edited by RONALD W. KOORBATSE DNA MAYNARD E. PULLMAN
VOLUME XI. Enzyme Structure
Edited yb C. H. W. HIRS
EMULOV XII. Nucleic Acids (Parts A and B)
Edited yb ECNERWAL NAMSSORG DNA KIVIE EVADLOM
EMULOV XIII. Citric Acid Cycle
Edited yb J. M. NIETSNEWOL
EMULOV XIV. Lipids
Edited yb J. M. NIETSNEWOL
EMULOV XV. Steroids and Terpenoids
Edited yb RAYMOND B. CLAYTON
EMULOV XVI. Fast Reactions
Edited yb KENNETH KUSTIN
xv
xvi SDOHTEM NI YGOLOMYZNE
EMULOV XVII. Metabolism of Amino Acids and Amines (Parts A and B)
Edited by TREBREH ROBAT DNA WHITE CELIA ROBAT
EMULOV XVIII. Vitamins and Coenzymes (Parts A, B, and C)
Edited by DLANOD B. KCIMROCcM DNA LEUMEL D. THGIRW
EMULOV XIX. Proteolytic Enzymes
Edited by EDURTREG E. NNAMLREP DNA OLZSAL DNAROL
EMULOV XX. Nucleic Acids and Protein Synthesis (Part C)
Edited by KIVIE EVADLOM DNA ECNERWAL NAMSSORG
EMULOV XXI. Nucleic Acids (Part D)
Edited by ECNERWAL NAMSSORG DNA KIVIE EVADLOM
EMULOV XXII. Enzyme Purification and Related Techniques
Edited yb WILLIAM B. YBOKAJ
EMULOV XXIII. Photosynthesis (Part A)
Edited by YNOHTNA NAS ORTEIP
EMULOV XXIV. Photosynthesis and Nitrogen Fixation (Part B)
Edited by YNOHTNA NAS ORTEIP
EMULOV XXV. Enzyme Structure (Part B)
Edited by C. H. W. HIRS DNA EGRES N. FFEHSAMIT
EMULOV XXVI. Enzyme Structure (Part C)
Edited by C. H. W. HIRS DNA EGRES N. FFEHSAMIT
EMULOV XXVII. Enzyme Structure (Part D)
Edited by C. H. W. HIRS DNA EGRES N. FFEHSAMIT
EMULOV XXVIII. Complex Carbohydrates (Part B)
Edited by ROTCIV GRUBSNIG
EMULOV XXIX. Nucleic Acids and Protein Synthesis (Part E)
Edited yb ECNERWAL NAMSSORG DNA KIVIE EVADLOM
EMULOV XXX. Nucleic Acids and Protein Synthesis (Part F)
Edited by KIVIE EVADLOM DNA ECNERWAL NAMSSORG
EMULOV XXXI. Biomembranes (Part A)
Edited by SIDNEY REHCSIELF DNA RETSEL REKCAP
EMULOV XXXII. Biomembranes (Part B)
Edited by SIDNEY REHCSIELF DNA RETSEL REKCAP
EMULOV XXXIII. Cumulative Subject Index Volumes I-XXX
Edited by AHTRAM G. DENNIS DNA DRAWDE A. SINNED
EMULOV XXXIV. Affinity Techniques (Enzyme Purification: Part )B
Edited yb WILLIAM B. YBOKAJ DNA MEIR KEHCLIW
EMULOV XXXV. Lipids (Part B)
Edited by JOHN M. NIETSNEWOL
SDOHTEM IN YGOLOMYZNE xvii
VOLUME XXXVI. Hormone Action (Part A: Steroid Hormones)
Edited by BERT W. O'MALLEY AND JOEL G. HARDMAN
VOLUME XXXVII. Hormone Action (Part B: Peptide Hormones)
Edited by BERT W. O'MALLEY DNA JOEL G. HARDMAN
VOLUME XXXVIII. Hormone Action (Part C: Cyclic Nucleotides)
Edited by JOEL G. HARDMAN DNA BERT W. O'MALLEY
VOLUME XXXIX. Hormone Action (Part D: Isolated Cells, Tissues, and Organ
Systems)
Edited by JOEL G. HARDMAN DNA BERT W. O'MALLEY
VOLUME XL. Hormone Action (Part E: Nuclear Structure and Function)
Edited by BERT W. O'MALLEY AND JOEL G. HARDMAN
VOLUME XLI. Carbohydrate Metabolism (Part B)
Edited by W. A. WOOD
VOLUME XLII. Carbohydrate Metabolism (Part C)
Edited by W. A. WOOD
VOLUME XLIII. Antibiotics
Edited by JOHN H. HASH
VOLUME XLIV. Immobilized Enzymes
Edited by KLAUS HCABSOM
VOLUME XLV. Proteolytic Enzymes (Part B)
Edited by LASZLO LORAND
VOLUME XLVI. Affinity Labeling
Edited by WILLIAM B. JAKOBY AND MEIR WILCHEK
VOLUME XLVII. Enzyme Structure (Part E)
Edited by C. H. W. HIRS DNA SERGE N. TIMASHEEE
VOLUME XLVIII. Enzyme Structure (Part F)
Edited by C. H. W. HIRS AND SERGE N. TIMASHEFF
VOLUME XLIX. Enzyme Structure (Part G)
Edited by C. H. W. HIRS DNA SERGE N. TIMASHEFE
VOLUME L. Complex Carbohydrates (Part C)
Edited by VICTOR GINSBURG
VOLUME LI. Purine and Pyrimidine Nucleotide Metabolism
Edited by PATRICIA A. HOFEEE DNA MARY ELLEN JONES
VOLUME LII. Biomembranes (Part C: Biological Oxidations)
Edited by SIDNEY FLEISCHER AND LESTER PACKER
VOLUME LIII. Biomembranes (Part D: Biological Oxidations)
Edited by SIDNEY FLEISCHER AND LESTER PACKER
VOLUME LIV. Biomembranes (Part E: Biological Oxidations)
Edited by SIDNEY FLEISCHER DNA LESTER PACKER
xviii SDOHTEM NI YGOLOMYZNE
EMULOV LV. Biomembranes (Part F: Bioenergetics)
Edited yb SIDNEY REHCSIELF DNA RETSEL REKCAP
EMULOV LVI. Biomembranes (Part G: Bioenergetics)
Edited by SIDNEY REHCSIELF DNA RETSEL REKCAP
EMULOV LVII. Bioluminescence and Chemiluminescence
Edited by ENELRAM A. DELUCA
EMULOV LVIII. Cell Culture
Edited by WILLIAM B. YBOKAJ DNA ARI NATSAP
EMULOV LIX. Nucleic Acids and Protein Synthesis (Part G)
Edited by KIVIE EVADLOM DNA ECNERWAL NAMSSORG
EMULOV LX. Nucleic Acids and Protein Synthesis (Part H)
Edited yb KIVlE EVADLOM DNA ECNERWAL NAMSSORG
EMULOV 61. Enzyme Structure (Part H)
Edited by C. H. W. HIRS DNA EGRES N. EEEHSAMIT
EMULOV 62. Vitamins and Coenzymes (Part D)
Edited by DLANOD B. McCORMICK DNA LEMUEL D. THGIRW
EMULOV 63. Enzyme Kinetics and Mechanism (Part A: Initial Rate and Inhibi-
tor Methods)
Edited by DANIEL L. HCIRUP
EMULOV 64. Enzyme Kinetics and Mechanism (Part B: Isotopic Probes and
Complex Enzyme Systems)
Edited by DANIEL L. HCIRUP
EMULOV 65. Nucleic Acids (Part I)
Edited by ECNERWAL NAMSSORG DNA KIVIE EVADLOM
EMULOV 66. Vitamins and Coenzymes (Part E)
Edited by DLANOD B. McCORMICK DNA LEUMEL D. THGIRW
EMULOV 67. Vitamins and Coenzymes (Part F)
Edited by DLANOD B. McCORMICK DNA LEMUEL D. THGIRW
EMULOV 68. Recombinant DNA
Edited by YAR Wu
EMULOV 69. Photosynthesis and Nitrogen Fixation (Part C)
Edited by YNOHTNA NAS ORTEIP
EMULOV 70. Immunochemical Techniques (Part A)
Edited by HELEN NAV SIKANUV DNA JOHN J. ENOGNAL
EMULOV 71. Lipids (Part C)
Edited by JOHN M. NIETSNEWOL
EMULOV 72. Lipids (Part D)
Edited by JOHN M. NIETSNEWOL
EMULOV 73. Immunochemical Techniques (Part B)
Edited by JOHN J. ENOGNAL DNA HELEN NAV SIKANUV
SDOHTEM IN YGOLOMYZNE XiX
EMULOV .47 Immunochemical Techniques (Part )C
Edited by JOHN J. LANGONE DNA HELEN VAN S1KANUV
EMULOV .57 Cumulative Subject Index Volumes XXXI, XXXII, XXXIV-LX
Edited by EDWARD A. DENNIS DNA MARTHA G. DENNIS
EMULOV .67 Hemoglobins
Edited by ERALDO ANTONINI, LUIGI ROSSI-BERNARDI, DNA EMILIA CHIAN-
ENOC
EMULOV .77 Detoxication and Drug Metabolism
Edited by WILLIAM B. YBOKAJ
EMULOV .87 Interferons (Part A)
Edited by SIDNEY AKTSEP
EMULOV .97 Interferons (Part )B
Edited by YENDIS AKTSEP
EMULOV .08 Proteolytic Enzymes (Part C)
Edited by OLZSAL DNAROL
EMULOV .18 Biomembranes (Part H: Visual Pigments and Purple Mem-
branes, I)
Edited by RETSEL REKCAP
EMULOV .28 Structural and Contractile Proteins (Part A: Extracellular Matrix)
Edited by LEON W. CUNN1NGHAM DNA DIXIE W. NESKIREDERF
EMULOV .38 Complex Carbohydrates (Part D)
Edited by ROTCIV GRUBSNIG
EMULOV .48 Immunochemical Techniques (Part D: Selected Immunoassays)
Edited by JOHN J. LANGONE DNA HELEN VAN VUNAKIS
EMULOV .58 Structural and Contractile Proteins (Part B: The Contractile Appa-
ratus and the Cytoskeleton)
Edited by DIXIE W. NESKIREDERF DNA LEON W. MAHGNINNUC
EMULOV .68 Prostaglandins and Arachidonate Metabolites
Edited by WILLIAM E. M. LANDS DNA WILLIAM L. SMITH
EMULOV .78 Enzyme Kinetics and Mechanism (Part C: Intermediates, Stereo-
chemistry, and Rate Studies)
Edited by DANIEL L. PURICH
EMULOV .88 Biomembranes (Part I: Visual Pigments and Purple Mem-
branes, II)
Edited by RETSEL REKCAP
EMULOV .98 Carbohydrate Metabolism (Part D)
Edited by WILLIS A. WOOD
EMULOV .09 Carbohydrate Metabolism (Part E)
Edited by WILLIS A. WOOD
EMULOV .19 Enzyme Structure (Part I)
Edited by C. H. W. HIRS DNA EGRES N. FFEHSAMIT
XX SDOHTEM NI YGOLOMYZNE
EMULOV 92. Immunochemical Techniques (Part E: Monoclonal Antibodies and
General Immunoassay Methods)
Edited by JOHN J. ENOGNAL DNA HELEN NAV SIKANUV
EMULOV .39 Immunochemical Techniques (Part F: Conventional Antibodies,
Fc Receptors, and Cytotoxicity)
Edited by JOHN J. ENOGNAL DNA HELEN NAV SIKANUV
EMULOV 94. Polyamines
Edited by TREBREH ROBAT DNA CELIA WHITE ROBAT
EMULOV 95. Cumulative Subject Index Volumes 61-74, 76-80
Edited by DRAWDE A. DENNIS DNA AHTRAM G. SINNED
EMULOV .69 Biomembranes Part J: Membrane Biogenesis: Assembly and
Targeting (General Methods; Eukaryotes)
Edited by SIDNEY REHCSIELF DNA ACCEB REHCSIELF
EMULOV 97. Biomembranes Part K: Membrane Biogenesis: Assembly and
Targeting (Prokaryotes, Mitochondria, and Chloroplasts)
Edited by SIDNEY REHCSIELF DNA ACCEB REHCSIELF
EMULOV 98. Biomembranes (Part L: Membrane Biogenesis: Processing and
Recycling)
Edited yb SIDNEY REHCSIELF DNA ACCEB REHCSIELF
EMULOV .99 Hormone Action (Part F: Protein Kinases)
Edited by EIKCAJ D. NIBROC DNA JOEL G. NAMDRAH
EMULOV 100. Recombinant DNA (Part B)
Edited by YAR Wu, ECNERWAL ,NAMSSORG DNA KIVIE EVADLOM
EMULOV 101. Recombinant DNA (Part C)
Edited by YAR Wu, ECNERWAL ,NAMSSORG DNA KIVIE EVADLOM
EMULOV 102. Hormone Action (Part G: Calmodulin and Calcium-Binding Pro-
teins)
Edited by YNOHTNA R. SNAEM DNA BERT W. O'MALLEY
EMULOV 103. Hormone Action (Part H: Neuroendocrine Peptides)
Edited by P. LEAHCIM NNOC
EMULOV 104. Enzyme Purification and Related Techniques (Part C)
Edited yb WILLIAM I. YBOKAJ
EMULOV 105. Oxygen Radicals in Biological Systems
Edited by RETSEL REKCAP
EMULOV 106. Posttranslational Modifications (Part A)
Edited by FINN WOLD DNA KIVIE EVADLOM
EMULOV 107. Posttranslational Modifications (Part B)
Edited by FINN WOLD DNA KIVIE EVADLOM
EMULOV 108. Immunochemical Techniques (Part G: Separation and Character-
ization of Lymphoid Cells)
Edited by INNAVOIG DI ,OTABAS JOHN J. ,ENOGNAL DNA
HELEN NAV SIKANUV