Advances in Carbohydrate Chemistry and Biochemistry (eBook)

Cover 1
Title Page 4
Copyright Page 5
Contents 6
Preface 10
George Alan Jeffery, 1915–2000 14
Sumio Umezawa, 1909–2000 24
Chapter 1. Sugar Derivatives Having Sulfur in the Ring 34
I. Introduction 34
II. Five-Membered Rings 35
III. Six-Membered Rings 68
IV. Seven-Membered Rings 91
V. Naturally Occurring 4-Thio and 5-Thio Sugar Analogues 98
References 99
Chapter 2. Helicobacter pylori: AWolf in Sheep’s Clothing: The Glycotype Families of Helicobacter pylori Lipopolysaccharides Expressing Histo-Blood Groups: Structure, Biosynthesis, and Role in Pathogenesis 112
I. Introduction 112
II. The Chemical Structure of Helicobacter pylori Type Strain Lipopolysaccharide: The Lewis X O-Chain 123
III. The Lewis Y and Sialyl Lewis X in Helicobacter pylori Lipopolysaccharides 131
IV. The Heptoglycan Domain in Helicobacter pylori Lipopolysaccharides 134
V. Semi Rough-Form and Smooth-Form Lipopolysaccharides in Helicobacter pylori: The Ubiquitous Phase Variation 139
VI. Type-1 Histo-Blood Groups in Helicobacter pylori Lipopolysaccharides and Their Prevalence in Asian Strains: The Lewis A, B, D, and Blood-Group A Determinants 143
VII. Glucosylated and Galactosylated Poly-N-acetyllactosamine O-Chains in Helicobacter pylori Lipopolysaccharides 150
VIII. Helicobacter pylori from Asymptomatic Hosts Expressing Heptoglycans, but Lacking Lewis O-Chains 153
IX. The Lipopolysaccharides of Helicobacter Species from Nonhuman Primates 157
X. Classification of Helicobacter pylori Lipopolysaccharides into Glycotype Families 159
XI. Concluding Remarks and Future Directions 165
References 167
Chapter 3. Structure and Biological Interactions of Heparin and Heparan Sulfate 172
I. Introduction 172
II. Biosynthesis 174
III. Structural Analysis 179
IV. Interaction with Proteins 195
V. Modified and Novel Structures 201
VI. Future Perspectives 207
References 208
Chapter 4. The Chemistry of Oligosaccharide Ligands of Selectins: Significance for the Development of New Immunomodulatory Medicines 220
I. Introduction 223
II. Selectins: Carbohydrate-Binding, Cell-Adhesion Molecules 227
III. Significance of Selectin–Ligand Interactions in Pathophysiology 268
IV. Syntheses of Oligosaccharides and Derivatives Corresponding to the Sialyl-Lewisx (sLex) and Sialyl-Lewisa (sLea) Determinants 278
V. Approaches to Pharmaceutically Applicable Inhibitors of Selectin–Carbohydrate Interactions 322
VI. Design of Inhibitors with Increased Binding Strength, Decreased Molecular Complexity, and Improved Feasibility of Large-Scale Synthesis 364
VII. Conclusions: Prospects, Alternatives, and Opportunities. 422
References 430
Author Index 450
Subject Index 494