ISBN-10:
0387949518
ISBN-13:
9780387949512
Pub. Date:
12/19/1997
Publisher:
Springer New York
Essentials of Carbohydrate Chemistry / Edition 1

Essentials of Carbohydrate Chemistry / Edition 1

by John F. Robyt

Hardcover

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Overview

This is the first broad treatment of carbohydrate chemistry in many years, and presents the structures, reactions, modifications, and properties of carbohydrates. Woven throughout the text are discussions of biological properties of carbohydrates, their industrial applications, and the history of the field of carbohydrate chemistry. Written for students as well as practising scientists, this textbook and handy reference will be of interest to a wide range of disciplines: biochemistry, chemistry, food and nutrition, microbiology, pharmacology, and medicine.

Product Details

ISBN-13: 9780387949512
Publisher: Springer New York
Publication date: 12/19/1997
Series: Springer Advanced Texts in Chemistry
Edition description: 1998
Pages: 399
Product dimensions: 6.10(w) x 9.25(h) x 0.36(d)

Table of Contents

1 Beginnings.- 1.1 Carbohydrates and Their Involvement in Life Processes.- 1.2 The Nature of Carbohydrates.- 1.3 Occurrence of Carbohydrates.- 1.4 Asymmetry and the Structures of Carbohydrates.- 1.5 Remembering the Structures of Carbohydrates.- 1.6 Derived Carbohydrate Structures.- a. Sugar Alcohols.- b. Sugar Acids.- c. Deoxy Sugars.- d. Amino Sugars.- e. Sugar Phosphates.- f. Condensed Sugar Products.- 1.7 Literature Cited.- 2 Developments.- 2.1 Carbohydrates in the History and Development of Human Culture.- 2.2 Development of Carbohydrate Chemistry.- a. Chemical Properties of Carbohydrates, 1860-1880.- b. Fischer’s Demonstration of the Structures of Glucose, Mannose, Arabinose, and Fructose.- 2.3 Cyclic Structures for the Carbohydrates.- 2.4 Naming the Anomeric Forms of Carbohydrates.- 2.5 Determination of the Size of Carbohydrate Rings.- 2.6 Conformational Structures of Cyclic Sugars.- 2.7 The Literature of Carbohydrate Chemistry.- 2.8 Chronological Summary of the Uses of Carbohydrates by Humans and the Development of Carbohydrate Chemistry.- 2.9 Specific Terms and Concepts Used in Carbohydrate Chemistry.- 2.10 Literature Cited.- 2.11 References for Further Study.- 3 Transformations.- 3.1 Mutarotation.- 3.2 Reactions of Carbohydrates with Strong Alkali.- 3.3 Alkaline Dehydration, Fragmentation, and Oxidation Reactions of Carbohydrates.- 3.4 Reactions of Carbohydrates with Strong Acid, and the Qualitative and Quantitative Determination of Carbohydrates.- 3.5 Reducing Reactions of Carbohydrates.- 3.6 Reactions of Hemiacetals or Hemiketals with Alcohols.- 3.7 Formation of Glycosidic Linkages to Give Di-, Tri-, and Oligosaccharides.- 3.8 Literature Cited.- 3.9 References for Further Study.- 4 Modifications.- 4.1 Formation of Carboxylic Acid Esters.- 4.2 Formation of Sulfonic Acid Esters.- 4.3 Formation of Ethers.- a. Methyl Ethers.- b. Trityl Ethers.- c. Benzyl Ethers.- d. Trialkylsilyl Ethers.- 4.4 Formation of Acetals and Ketals.- 4.5 Modifications at C-1.- a. Reduction of Aldehyde and Ketone Carbonyls.- b. Reduction of Thioacetals and the Protection of C-1.- c. Oxidation of C-1.- d. Chain Elongation.- e. Chain-Length Reduction.- f. Substitution at C-1, the Reducing Carbon.- g. Formation of Glycosides.- h. Formation of Glycosidic Linkages between Monosaccharide Residues.- 4.6 Modifications at C-2.- 4.7 Modifications at C-3.- 4.8 Modifications at C-4.- 4.9 Modifications at C-5 and Substitution for the Ring Oxygen.- 4.10 Modifications of C-6 in Hexopyranoses.- 4.11 Summary of the Strategies Presented for the Chemical Modification of Carbohydrates.- 4.12 Literature Cited.- 4.13 References for Further Study.- 5 Sweetness.- 5.1 The Sweet Taste of Sugars and the Development of the Sweet-Taste Hypothesis.- 5.2 Naturally Occurring Sweet Glycosides.- 5.3 Synthesis of Supersweet Sucroses.- 5.4 Literature Cited.- 5.5 References for Further Study.- 6 Polysaccharides I:Structure and Function.- 6.1 Introduction: Structure and Classification of Polysaccharides.- 6.2 Plant Polysaccharides.- a. Starch.- b. Cellulose.- c. Hemicelluloses.- d. Pectins.- e. Exudate Gums.- f. Fructans.- g. Seaweed Polysaccharides.- h. Dietary Fibers.- 6.3 Animal Polysaccharides.- a. Glycogen.- b. Glycosaminoglycans.- c. Chitin.- 6.4 Microbial Polysaccharides.- a. Murein.- b. Dextrans and Related Polysaccharides: Mutan and Alternan.- c. Pullulan.- d. Bacterial Fructans.- e. Xanthan.- f. Bacterial Gels.- g. Pneumococcal Capsule Polysaccharides.- h.SalmonellaO-Antigen Polysaccharides.- i. Capsular Polysaccharides of Other Gram-Negative Bacteria.- 6.5 Teichoic Acids.- 6.6 Simplified Representation of Oligosaccharide and Polysaccharide Structures.- 6.7 Literature Cited.- 6.8 References for Further Study.- 7 Polysaccharides II:Chemical Modificationsand Their Applications.- 7.1 Introduction.- 7.2 Formation of Polysaccharide Esters.- 7.3 Formation of Polysaccharide Ethers.- 7.4 Formation of Cross-linked Polysaccharide Ethers.- 7.5 Polysaccharide Phosphates.- 7.6 Polysaccharide Sulfates.- 7.7 Polysaccharide Dye Derivatives.- 7.8 Activation of Polysaccharides for Covalently Attaching Ligands and Proteins.- 7.9 Oxidation of Primary Alcohols of Polysaccharides to Carboxyl Groups.- 7.10 Periodate Oxidation of Polysaccharides.- 7.11 Miscellaneous Modifications of Alcohol Groups of Polysaccharides.- 7.12 Modification of Starch Granules by Acid Hydrolysis.- 7.13 Literature Cited.- 8 Cyclodextrins.- 8.1 Cyclomaltodextrins.- 8.2 Cyclic (?-1— 2 Glucans (Cyclosophorans).- 8.3 Cyclic (?-1— 6 and—-1— 3D-Glucans.- 8.4 Cycloisomaltodextrins.- 8.5 Cycloalternanotetraose (Alternating—-1— 6/?-1— 3 Cyclotetraose).- 8.6 Cycloinulodextrin.- 8.7 Chemical Synthesis of Cyclodextrins.- 8.8 Macrocyclic Maltodextrins.- 8.9 Literature Cited.- 8.10 References for Further Study.- 9 GIycoconjugates.- 9.1 Introduction.- 9.2 Structures ofN-Linked Glycosides in Glycoproteins.- 9.3 Structures ofO-Linked Glycosides in Glycoproteins.- 9.4 Structures of Glycolipids.- a. Glycoglycerolipids.- b. Glycosphingolipids.- c. Glycosyl Pyrophospho Polyprenols.- d. Lipopolysaccharide of Gram-Negative Bacteria.- 9.5 Literature Cited.- 9.6 References for Further Study.- 10 Biosynthesis.- 10.1 Photosynthesis and the Formation of Carbohydrates.- 10.2 Biosynthesis of Sugar Nucleotides.- 10.3 Biosynthesis of Different Monosaccharides by Epimerization, Oxidation, and Decarboxylation.- 10.4 Biosynthesis ofD- andL-6-Deoxyhexoses.- 10.5 Biosynthesis of Eight-and Nine-Carbon Sugars:N-Acetyl-D-Neuraminic Acid,N-Acetyl-D-Muramic Acid, and 2-Keto-3-Deoxy-D-Mannooctulosonic Acid (KDO).- 10.6 Biosynthesis of the Naturally Occurring Disaccharides:—,—-Trehalose, Sucrose, and Lactose.- 10.7 Biosynthesis of Sucrose and Starch in Plants.- 10.8 Biosynthesis of the Bacterial Cell Wall: Peptidomurein.- 10.9 Biosynthesis of theSalmonellaO-Antigen Outer Capsular Polysaccharide.- 10.10 Biosynthesis ofEscherichia coliandNeisseria meningitidesColominic Acid.- 10.11 Biosynthesis of Teichoic Acids.- 10.12 Biosynthesis of Dextrans and Related Polysaccharides.- 10.13 Biosynthesis of Starch, Glycogen, and Cellulose.- 10.14 Biosynthesis of Glycoproteins.- 10.15 Literature Cited.- 10.16 References for Further Study.- 11 Biodegradation.- 11.1 Digestion of Starch.- 11.2 Hydrolysis of Starch by Microorganisms.- 11.3 Biodegradation of Starch and Dextran to Cyclodextrins.- 11.4 Biodegradation of Liver and Muscle Glycogen.- 11.5 Biodegradation of Cellulose and Related Polysaccharides.- 11.6 Chemical Energy from Carbohydrates.- 11.7 Literature Cited.- 12 Determinations.- 12.1 Determination of the Presence of Carbohydrate.- 12.2 Purification of Carbohydrates.- 12.3 Monosaccharide Composition of Carbohydrates.- 12.4 Determination of the Positions of Glycosidic Linkage.- 12.5 Determination of the Position of Substitution of Monosaccharide Residue(s) by Periodate Oxidation.- 12.6 Configuration of Glycosidic Linkages.- 12.7 Sequence of Monosaccharides and Their Linkages.- 12.8 Use of Enzymes in Determining Structure.- 12.9 Determination of Carbohydrate Structure by Using NMR.- 12.10 Separation and Determination of Carbohydrate Structure by Using Lectins.- 12.11 Removal of Glycosides from Glycoproteins for Structure Determination.- 12.12 Literature Cited.- 12.13 References for Further Study.- Appendix A.- Primer on Carbohydrate Nomenclature.- Appendix B.- Primer on Enzyme Names and Their Catalyzed Reactions.

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