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Essentials of Carbohydrate Chemistry


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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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