Overview

To exploit the full potential of this diverse compound class for the development of novel active substances, this handbook presents the latest knowledge on carbohydrate chemistry and biochemistry. While it is unique in covering the entire field, particular emphasis is placed on carbohydrates with pharmaceutical potential. Topics include the following: > Chemical Synthesis of Carbohydrates > Carbohydrate Biosynthesis and Metabolism > Carbohydrate Analysis > Cellular Functions of Carbohydrates > Development of Carbohydrate-based Drugs A premier resource for carbohydrate chemists and drug developers, this comprehensive two-volume work contains contributions by more than 50 of the world's leading carbohydrate chemists.

Full Product Details

Author:   Chi-Huey Wong (Scripps Res. Inst. La Jolla, California)
Publisher:   Wiley-VCH Verlag GmbH
Imprint:   Blackwell Verlag GmbH
Dimensions:   Width: 17.80cm , Height: 5.80cm , Length: 24.60cm
Weight:   2.136kg
ISBN:  

9783527306329

ISBN 10:   3527306323
Pages:   980
Publication Date:   16 September 2003
Audience:   Professional and scholarly ,  Professional & Vocational
Format:   Hardback
Publisher's Status:   Active
Availability:   Out of stock  
The supplier is temporarily out of stock of this item. It will be ordered for you on backorder and shipped when it becomes available.

Table of Contents

Volume 1 Preface xxv List of Contributors xxvii 1 Synthetic Methodologies 1 Chikako Saotome and Osamu Kanie 1.1 Introduction 1 1.2 Tactical Analysis for Overall Synthetic Efficiency 1 1.3 Methodological Improvements 2 1.4 Accessibility 11 1.5 Concluding Remarks 32 1.6 References 33 2 Complex Carbohydrate Synthesis 37 Makoto Kiso, Hideharu Ishida, and Hiromune Ando 2.1 Introduction 37 2.2 Synthetic Gangliosides 38 2.3 Toxin Receptor 50 2.4 Summary and Perspectives 52 2.5 References 52 3 The Chemistry of Sialic Acid 55 Geert-Jan Boons and Alexei V. Demchenko 3.1 Introduction 55 3.2 Chemical and Enzymatic Synthesis of Sialic Acids 56 3.3 Chemical Glycosidation of Sialic Acids 59 3.4 Enzymatic Glycosidations of Sialic Acids 83 3.5 Synthesis of C- and S-Glycosides of Sialic Acid 91 3.6 Modifications at N-5 94 3.7 References 95 4 Solid-Phase Oligosaccharide Synthesis 103 Peter H. Seeberger 4.1 Introduction 103 4.2 Pioneering Efforts in Solid-Phase Oligosaccharide Synthesis 104 4.3 Synthetic Strategies 105 4.4 Support Materials 107 4.5 Linkers 108 4.6 Synthesis of Oligosaccharides on Solid Support by Use of Different Glycosylating Agents 112 4.7 Automated Solid-Phase Oligosaccharide Synthesis 118 4.8 Conclusion and Outlook 124 4.9 References 125 5 Solution and Polymer-Supported Synthesis of Carbohydrates 129 Shin-Ichiro Nishimura 5.1 Introduction 129 5.2 Mimicking Glycoprotein Biosynthetic Systems 130 5.3 References 136 6 Enzymatic Synthesis of Oligosaccharides Jianbo Zhang, Jun Shao, Prezemk Kowal, and Peng George Wang 6.1 Introduction 137 6.2 Sugar Nucleotide Biosynthetic Pathways 140 6.3 Enzymatic Oligosaccharide Synthesis Processes 151 6.4 Future Directions 162 6.5 References 162 7 Glycopeptides and Glycoproteins: Synthetic Chemistry and Biology 169 Oliver Seitz 7.1 Introduction 169 7.2 The Glycosidic Linkage 169 7.3 The Challenges of Glycopeptide Synthesis 171 7.4 Synthesis of Preformed Glycosyl Amino Acids 173 7.5 Synthesis of Glycopeptides 181 7.6 Biological and Biophysical Studies 200 7.7 Summary and Outlook 208 7.8 References 209 8 Synthesis of Complex Carbohydrates: Everninomicin 13,384-1 215 K. C. Nicolaou, Helen J. Mitchell, and Scott A. Snyder 8.1 Introduction 215 8.2 Retrosynthetic Analysis and Strategy 218 8.3 Total Synthesis of Everninomicin 13,384-1 (1) 223 8.4 Conclusion 249 8.5 References 250 9 Chemical Synthesis of Asparagine-Linked Glycoprotein Oligosaccharides: Recent Examples 253 Yukishige Ito and Ichiro Matsuo 9.1 Introduction 253 9.2 Synthesis of Asn-Linked Oligosaccharides: Basic Principles 257 9.3 Chemical Synthesis of Complex Oligosaccharides 261 9.4 References 278 10 Chemistry and Biochemistry of Asparagine-Linked Protein Glycosylation 281 Barbara Imperiali and Vincent W.-F. Tai 10.1 Protein Glycosylation 281 10.2 Small-Molecule Probes of the Biochemistry of Oligosaccharyl Transferase 283 10.3 Conclusions 301 10.4 References 301 11 Conformational Analysis of C-Glycosides and Related Compounds: Programming Conformational Profiles of C- and O-Glycosides 305 Peter G. Goekjian, Alexander Wei, and Yoshito Kishi 11.1 Introduction 305 11.2 Stereoelectronic Effects and te exo-Anomeric Conformation 306 11.3 Conformational Analysis of C-Glycosides: C-Monoglycosides 309 11.4 1,4-Linked C-Disaccharides: the Importance of syn-Pentane Interactions 314 11.5 Prediction of Conformational Preference and Experimental Validation 318 11.6 Programming Oligosaccharide Conformation 322 11.7 Conformational Design of C-Trisaccharides based on a Human Blood Group Antigen 323 11.8 Conformational Design: Relationship to Biological Activity 330 11.9 Concluding Remarks 336 11.10 Acknowledgements 337 11.11 References 337 12 Synthetic Lipid A Antagonists for Sepsis Treatment 341 William J. Christ, Lynn D. Hawkins, Michael D. Lewis, and Yoshito Kishi 12.1 Background 341 12.2 Hypothesis and Approach 342 12.3 Conclusion 351 12.4 Acknowledgement 353 12.5 References 353 13 Polysialic Acid Vaccines 357 Harold J. Jennings 13.1 Introduction 357 13.2 Group C Meningococcal Vaccines 358 13.3 Group B Meningococcal Vaccines 362 13.4 Chemically Modified Group B Meningococcal Vaccines 366 13.5 Cancer Vaccines 371 13.6 Acknowledgements 375 13.7 References 375 14 Synthetic Carbohydrate-Based Vaccines 381 Stacy J. Keding and Samuel J. Danishefsky 14.1 Introduction 381 14.2 Cancer Vaccines 382 14.3 Bacterial Polysaccharide Vaccines 397 14.4 Synthetic Parasitic Polysaccharide Conjugate Vaccine 402 14.5 Conclusions 403 14.6 References 403 15 Chemistry, Biochemistry, and Pharmaceutical Potentials of Glycosaminoglycans and Related Saccharides 407 Tasneem Islam and Robert J. Linhardt 15.1 Introduction 407 15.2 Dermatan and Chondroitin Sulfates 417 15.3 Hyaluronan 419 15.4 Keratan Sulfate 423 15.5 Other Acidic Polysaccharides 425 15.6 Pharmaceutical Potential and Challenges 430 15.7 Conclusion 432 15.8 References 433 16 A New Generation of Antithrombotics Based on Synthetic Oligosaccharides 441 Maurice Petitou and Jean-Marc Herbert 16.1 Introduction 441 16.2 Heparin and Its Mechanism of Action as an Antithrombotic Agent 442 16.3 Synthetic Pentasaccharides, Selective Factor Xa Inhibitors, are Antithrombotic Agents 446 16.4 Synthetic Thrombin-Inhibiting Oligosaccharides: The Next Generation? 452 16.5 The Mechanism of Antithrombin Activation by Synthetic Oligosaccharides 456 16.6 Conclusion and Perspectives 456 16.7 References 457 Volume 2 17 Sequencing of Oligosaccharides and Glycoproteins 461 Stuart M. Haslam, Kay-Hooi Khoo, and Anne Dell 17.1 Mass Spectrometry 462 17.2 MS-Based Sequencing Strategies 466 17.3 Glycan Sequencing and Structural Determination – A Case Study 470 17.4 Mammalian Glycomics 475 17.5 Some Special Case Strategies 477 17.6 References 481 18 Preparation of Heterocyclic 2-Deoxystreptamine Aminoglycoside Analogues and Characterization of their Interaction with RNAs by Use of Electrospray Ionization Mass Spectrometry 483 Richard H. Griffey, Steven A. Hofstadler, and Eric E. Swayze 18.1 Introduction 483 18.2 ESI-MS for Characterization of Aminoglycoside-RNA Interactions 484 18.3 Preparation of Heterocyclic 2-Deoxystreptamines and Binding to a 16S A Site RNA Model 490 18.4 Preparation, Binding, and Biological Activity of Substituted Paromomycin Derivatives 495 18.5 Future Prospects 498 18.6 Acknowledgements 498 18.7 References 498 19 Glycosylation Analysis of a Recombinant P-Selectin Antagonist by High-pH Anion-Exchange Chromatography with Pulsed Electrochemical Detection (HPAEC/PED) 501 Mark R. Hardy and Richard J. Cornell 19.1 Introduction 501 19.2 Use of HPAEC/PED in the Development of Biopharmaceuticals 502 19.3 Biology of P-Selectin 503 19.4 HPAEC/PED as an Adjunct to rPSGL-Ig Process Development 504 19.5 Results and Discussion 508 19.6 Summary 515 19.7 Acknowledgements 516 19.8 References 516 20 Analytical Techniques for the Characterization and Sequencing of Glycosaminoglycans 517 Ram Sasisekharan, Zachary Shriver, Mallik Sundaram, and Ganesh Venkataraman 20.1 Introduction to GAG Linear Complex Polysaccharides 517 20.2 Depolymerization of Nascent GAG Chains 521 20.4 Analytical Tools Used in the Structural Characterization of GAGs 527 20.5 Future Directions 536 20.6 Acknowledgements 537 20.7 References 537 21 Thermodynamic Models of the Multivalency Effect 541 Pavel I. Kitov and David R. Bundle 21.1 Introduction 541 21.2 Concept of Distribution Free Energy 542 21.3 Multivalent Receptor vs. Monovalent Ligand 546 21.4 Multivalent Receptor vs. Multivalent Ligand 551 21.5 Topological Classification of Multivalent Systems 553 21.6 Determination of Microscopic Binding Parameters by Molecular Modeling 555 21.7 Determination of Microscopic Binding Parameters from Binding Data 561 21.8 Thermodynamic Analysis of Multivalent Interaction 562 21.9 Conclusions 570 21.10 Mathematical Appendix 570 21.10.1 Calculation of Statistical Coefficients 570 21.10.2 Multivalent Receptor and Monovalent Ligand 571 21.10.3 Multivalent Binding with Linear and Circular Topology 571 21.10.4 Multivalent Binding with Radial Topology 572 21.10.5 Derivation of Eq. (24) 572 21.11 References 573 22 Synthetic Multivalent Carbohydrate Ligands as Effectors or Inhibitors of Biological Processes 575 Laura L. Kiessling, Jason K. Pontrello, and Michael C. Schuster 22.1 Introduction 575 22.2 Multivalent Carbohydrate Ligands as Inhibitors 581 22.3 Multivalent Carbohydrate Ligands as Effectors 596 22.4 Conclusions 605 22.5 References 605 23 Glycosyltransferase Inhibitors 609 Karl-Heinz Jung and Richard R. Schmidt 23.1 Introduction 609 23.2 Glycosyltransferases Utilizing NDP-Sugar Donors 610 23.3 Glycosyltransferases Utilizing NMP-Sugar Donors 641 23.4 Bisubstrate Analogues as Inhibitors 648 23.5 Conclusion 653 23.6 References 654 24 RNA-Aminoglycoside Interactions 661 Haim Weizman and Yitzhak Tor 24.1 RNA as an Emerging Therapeutic Target 661 24.2 Aminoglycoside Antibiotics: Past and Present 664 24.3 Aminoglycosides as RNA Binders 666 24.4 Identifying RNA Targets and Developing Binding Assays 670 24.5 Dimeric Aminoglycosides 673 24.6 Aminoglycoside-Intercalator Conjugates 675 24.7 Guanidinoglycosides 677 24.8 Summary and Outlook 679 24.9 Acknowledgements 680 24.10 References 680 25 Glycosylated Natural Products 685 Jon S. Thorson and Thomas Vogt 25.1 Introduction 685 25.2 A Summary of Bioactive Glycosylated Secondary Metabolites 686 25.3 Conclusions 707 25.4 References 707 26 Novel Enzymatic Mechanisms in the Biosynthesis of Unusual Sugars 713 Alexander Wong, Xuemei He, and Hung-Wen Liu 26.1 Introduction 713 26.2 Biosynthesis of Deoxysugars 714 26.3 Biosynthesis of Aminosugars 725 26.4 Biosynthesis of Branched-Chain Sugars 730 26.5 Epimerization Reactions 734 26.6 Rearrangement of Hexose Skeletons: UDP-Galactopyranose Mutase-Catalyzed Biosynthesis of Galactofuranose 738 26.7 Summary 740 26.8 Acknowledgements 741 26.9 References 741 27 Neoglycolipids: Identification of Functional Carbohydrate Epitopes 747 Ten Feizi, Alexander M. Lawson, and Wengang Chai 27.1 Rationale for Developing Neoglycolipids as Oligosaccharide Probes 747 27.2 The First and Second Generation Neoglycolipids 749 27.3 Mass Spectrometry of Neoglycolipids 750 27.4 Scope of the Neoglycolipid Technology 752 27.5 Oligosaccharide Microarrays 755 27.6 Summary and Perspectives 757 27.7 Acknowledgement 757 27.8 References 757 28 A Preamble to Aglycone Reconstruction for Membrane-Presented Glycolipid Mimics 761 Murugesapillai Mylvaganam and Clifford A. Lingwood 28.1 Introduction 761 28.2 The Role of Ceramide Subtype Composition 762 28.3 Effects of Ceramide Subtype Composition in the Binding of Gb3Cer to Verotoxins 764 28.4 Hypothesis Regarding Lipid Replacement Structural Motifs (LRSMs) 766 28.5 Effect of Replacement of GSL Fatty Acyl Chains with Rigid, Non-Planar Hydrophobic Groups 768 28.6 Ada-Gb3Cer, a Functional Mimic of Membrane Presented Gb3Cer for VT Binding 769 28.7 Ceramide Subtype-Dependent Binding of Heat Shock Protein Hsp70 to Sulfogalactosyl Ceramide 772 28.8 Adamantyl-Acyl Ceramide is a Functional Replacement for a Ceramide-Cholesterol Composition: A Study with HIV Coat Protein gp120 775 28.9 Acknowledgement 777 28.10 References 777 29 Small Molecule Inhibitors of the Sulfotransferases 781 Dawn E. Verdugo, Lars C. Pedersen, and Carolyn R. Bertozzi 29.1 Introduction: Sulfotransferases and the Biology of Sulfation 781 29.2 EST as a Model ST for Inhibitor Design 783 29.3 Inhibition of Representative Golgi-Resident Sulfotransferases: GST-2, GST-3, and TPST-2 792 29.4 Assays for High-Throughput Screening of STs 794 29.5 New Directions in Inhibitor Discovery 796 29.6 Conclusions 796 29.7 Acknowledgements 796 29.8 References 797 30 Carbohydrate-Based Treatment of Cancer Metastasis 803 Reiji Kannagi 30.1 Implication of Carbohydrate Determinants in Cancer Metastasis 803 30.2 Tumor Angiogenesis and Cancer-Endothelial Interaction 808 30.3 Use of Monoclonal Antibodies for Inhibition of Cancer Cell-Endothelial Interaction 809 30.4 Inhibitors of Selectin-Mediated Cell Adhesion 812 30.5 Regulation of Selectin Expression on Endothelial Cells 814 30.6 Enhanced Expression of Sialyl Lex and Sialyl Lea in Malignant Cells and its Modulation 816 30.7 References 824 31 N-Acetylneuraminic Acid Derivatives and Mimetics as Anti-Influenza Agents 831 Robin Thomson and Mark von Itzstein 31.1 Introduction 831 31.2 Structure-Based Design of Inhibitors of Influenza Virus Sialidase 836 31.3 Structure/Activity Relationship Studies of N-Acetylneuraminic Acid-Based Influenza Virus Sialidase Inhibitors 840 31.4 Concluding Remarks 856 31.5 Acknowledgements 856 31.6 References 857 32 Modified and Modifying Sugars as a New Tool for the Development of Therapeutic Agents – The Biochemically Engineered N-Acyl Side Chain of Sialic Acid: Biological Implications and Possible Uses in Medicine 863 Rüdiger Horstkorte, Oliver T. Keppler, and Werner Reutter 32.1 Introduction 863 32.2 N-Acyl Side Chain-Modified Precursors of Sialic Acid 865 32.3 Outlook 871 32.4 Acknowledgements 872 32.5 Abbreviations 872 32.6 References 872 33 Modified and Modifying Sugars as a New Tool for the Development of Therapeutic Agents – Glycosidated Phospholipids as a New Type of Antiproliferative Agents 875 Kerstin Danker, Annette Fischer, and Werner Reutter 33.1 Introduction 875 33.2 Structures of Synthetic Glycosidated Phospholipid Analogues 876 33.3 Antiproliferative Effect and Cytotoxicity of Glycosidated Phospholipid Analogues in Cell Culture Systems 876 33.4 Effect of Glycosidated Phospholipid Analogues on Cell Matrix Adhesion 878 33.5 Mechanisms of Action 879 33.6 Outlook and New Developments 880 33.7 Acknowledgements 881 33.8 References 881 34 Glycoside Primers and Inhibitors of Glycosylation 883 Jillian R. Brown, Mark M. Fuster, and Jeffrey D. Esko 34.1 Introduction 883 34.2 Glycoside-Based Substrates 883 34.3 Glycoside Primers – Xylosides 884 34.4 Other Types of Primers 885 34.5 Glycosides as Metabolic Decoys 888 34.6 Analogues 890 34.7 References 892 35 Carbohydrate-Based Drug Discovery in the Battle Against Bacterial Infections: New Opportunities Arising from Programmable One-Pot Oligosaccharide Synthesis 899 Thomas K. Ritter and Chi-Huey Wong 35.1 Introduction 899 35.2 Cell-Surface Carbohydrates 900 35.3 Peptidoglycan 904 35.4 Macrolide Antibiotics 913 35.5 Aminoglycosides 917 35.6 Programmable One-Pot Oligosaccharide Synthesis 922 35.7 Summary 927 35.8 References 928 Subject Index 933

Reviews

In summary, Carbohydrate-Based Drug Discovery Vols. 1 and 2 provide an appropriate and useful look at the current state of the art in this relevant and rapidly advancing field. I recommend the book to both experts and less expert readers. ( ChemBioChem, April 2004) To summarize, the work provides a comprehensive and excellent survey of the present situation in carbohydrate research, in which many interesting details can be spotted. Because of the wide range of topics covered, the reader will refer to it again and again. It is likely to become a standard work on the subject, not exclusively for carbohydrate chemistry enthusiasts. (Angewandte Chemie + IE, 2004-43/31)

In summary, Carbohydrate-Based Drug Discovery Vols. 1 and 2 provide an appropriate and useful look at the current state of the art in this relevant and rapidly advancing field. I recommend the book to both experts and less expert readers. (ChemBioChem, April 2004) To summarize, the work provides a comprehensive and excellent survey of the present situation in carbohydrate research, in which many interesting details can be spotted. Because of the wide range of topics covered, the reader will refer to it again and again. It is likely to become a standard work on the subject, not exclusively for carbohydrate chemistry enthusiasts. (Angewandte Chemie + IE, 2004-43/31)

Author Information

Professor Chi-Huey Wong received his B.S. and M.S. degrees from National Taiwan University, and Ph.D. in Chemistry (with George Whitesides) from Massachusetts Institute of Technology in 1982. He started his independent career as Assistant Professor of Chemistry at Texas A&M University in 1983, where he became Full Professor in 1987. He has been Professor and Ernest W. Hahn Chair in Chemistry at the Scripps Research Institute since 1989 and is also a member of the Skaggs Institute for Chemical Biology since 1996. Professor Wong is a member of the U.S. National Academy of Sciences and the American Academy of Arts and Sciences. He is a recipient of The Searle Scholar Award in Biomedical Sciences (1985), the Presidential Young Investigator Award in Chemistry (1986), the American Chemical Society A.C. Cope Scholar Award (1993), the Roy Whistler Award of the International Carbohydrate Organization (1994), the American Chemical Society Harrison Howe Award in Chemistry (1998) and the Claude S. Hudson Award in Carbohydrate Chemistry (1999), the International Enzyme Engineering Award (1999) and the Presidential Green Chemistry Challenge Award (2000). He is a member of Academia Sinica, Taipei (1994), the American Academy of Arts and Sciences (1996) and the US National Academy of Sciences (2002). He serves as editor-in-chief of Bioorganic and Medicinal Chemistry and is an executive board member of the Tetrahedron Publications. He was head of the Frontier Research Program on Glycotechnology at RIKEN (Institute of Physical and Chemical Research, Japan) (1991-1999) and is currently a scientific advisor of the Max-Planck Institute, a board member of the U.S. National Research Council on Chemical Sciences and Technology, and is a founding scientist of Optimer Pharmaceuticals, Inc. He is author and co-author of over 450 publications, 60 patents and several books. His current interests are in the areas of bioorganic and synthetic chemistry and biocatalysis, including development of new synthetic chemistry based on enzymatic and chemo-enzymatic reactions, synthetic approach to carbohydrate-mediated biological recognition, design and synthesis of mechanism-based inhibitors of enzymes, RNA and carbohydrate receptors, development of oligosaccharide and aminoglycoside microarrays for high-throughput screening and the study of reaction mechanisms.

Tab Content 6

Author Website:  

Customer Reviews

Recent Reviews

No review item found!

Add your own review!

Countries Available

All regions