Advances in Carbohydrate Chemistry and Biochemistry / Edition 1

Advances in Carbohydrate Chemistry and Biochemistry / Edition 1

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by Derek Horton, Horton
     
 

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ISBN-10: 0120072556

ISBN-13: 9780120072552

Pub. Date: 01/24/2000

Publisher: Elsevier Science

Since its inception in 1945, this serial has provided critical and integrating articles written by research specialists that integrate industrial, analytical, and technological aspects of biochemistry, organic chemistry, and instrumentation methodology in the study of carbohydrates. The articles provide a definitive interpretation of the current status and future

Overview

Since its inception in 1945, this serial has provided critical and integrating articles written by research specialists that integrate industrial, analytical, and technological aspects of biochemistry, organic chemistry, and instrumentation methodology in the study of carbohydrates. The articles provide a definitive interpretation of the current status and future trends in carbohydrate chemistry and biochemistry.

Product Details

ISBN-13:
9780120072552
Publisher:
Elsevier Science
Publication date:
01/24/2000
Series:
Advances in Carbohydrate Chemistry and Biochemistry Series
Edition description:
New Edition
Pages:
365
Product dimensions:
6.10(w) x 9.10(h) x 0.80(d)

Table of Contents

Prefaceix
Guy Gordon Studdy Dutton, 1923-1997
Text1
Iodine in Carbohydrate Chemistry
I.Introduction9
II.Glycosylation10
1.Uses of Iodine10
2.Glycosyl Iodides10
3.Activation of n-Pentenyl Glycosides13
4.Activation of Thioglycosides15
III.Activation of Glycals19
IV.Pseudohalogens26
V.Hypervalent Iodine30
1.Dess-Martin Reagent36
VI.Reactions Involving Phosphorus38
1.Rydon Reagents38
2.The Garegg-Samuelsson Reagent39
VII.Installation and Removal of Protecting Groups Using Iodine44
VIII.Iodocyclizations50
IX.Miscellaneous Reactions55
References57
Structure of Anomeric Glycosyl Radicals and Their Transformations under Reductive Conditions
I.Introduction65
II.Structure of Sugar-Derived Radicals67
1.Structure of Carbon-Centered Acetal Radicals68
2.ESR Studies of Carbohydrate-Derived Radicals69
3.Interpretation in the Framework of the Frontier Molecular Orbital (FMO) Theory85
III.Radical Methods to Anhydroalditols from Glycosyl Derivatives86
1.Radical Reduction with Tin and Silicon Hydrides87
2.Synthesis of Anhydroalditols by Single-Electron Transfer100
3.Synthesis of Ring-Fused and C-Branched Anhydroalditols102
4.Stereoselectivity of Hydrogen-Atom Transfer at Anomeric Radicals103
IV.Diastereoselective Reductions of Substituted Anomeric Radicals106
1.Stereocontrolled Synthesis of O-Glycosides and Analogs107
2.Stereocontrolled Synthesis of C-Glycosyl Compounds and Analogues115
3.Radical Routes to Nucleosides127
4.Reduction Diastereoselectivity of Substituted Anomeric Radicals129
V.Synthesis of 2-Deoxy Sugars by Radical-Induced Rearrangement130
1.Synthesis of 2-Deoxy Sugars by 2,1-Acyloxy Group Rearrangements131
2.Synthesis of 2-Deoxy Sugars by 2,1-Phosphonyloxy Group Rearrangement135
3.Mechanism of Radical-Induced 2,1-Migrations of Ester Groups138
VI.Radical-Mediated Eliminations: Formation of Glycals139
VII.Conclusion142
References143
Oligosaccharide-Protein Conjugates as Vaccine Candidates against Bacteria
I.Overview of Polysaccharide-Based Antibacterial Vaccines153
II.Synthesis and Immunological Evaluation of Protein Conjugates of Oligosaccharide Components of Bacterial Polysaccharides157
1.Studies on Dextran-Related Oligosaccharide-Protein Conjugates157
2.Protein Conjugates of Oligosaccharide Fragments of Capsular Polysaccharides161
3.Protein Conjugates of Oligosaccharides Related to Lipopolysaccharides179
III.Conclusion193
References194
Molecular Structure of the Carbohydrate-Protein Linkage Region Fragments from Connective-Tissue Proteoglycans
I.Introduction201
II.Isolation of Linkage-Region Oligosaccharides205
III.Identification of Carbohydrate Spin Systems206
IV.Identification of the Peptide Spin Systems209
V.Conformational Analysis of the Interglycosidic Linkages210
VI.Conformation of the Glycopeptide Linkage211
VII.Influence of Glycosylation on Proteoglycan Core-Peptide Backbone Conformation213
VIII.Structural Studies on the Carbohydrate-Protein Linkage Region215
1.Dermatan Sulfate215
2.Chondroitin Sulfate216
3.Heparan Sulfate219
4.Heparin223
IX.NMR Spectral Properties of Linkage-Region Oligosaccharides224
X.Biosynthesis of Carbohydrate-Protein Linkage-Region Oligosaccharides228
References229
The Conformation of C-Glycosyl Compounds
I.Introduction235
II.Nomenclature236
III.C-Glycosyl Compounds in Chemistry and Biochemistry237
IV.Conformation of Saccharides: An Overview on the Relative Role of the Exoanomeric Effect and Steric Interactions239
V.The Use of NMR and Molecular Modeling as Tools in Conformational Analysis of C-Glycosyl Compounds in Solution243
VI.Conformation of C-Glycosyl Compounds246
1.Conformation in the Solid State246
2.Conformation in Solution247
VII.Conclusions279
References280
Author Index285
Subject Index311

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