Carbohydrates

Comprehensive Biochemisty, Volume 5: Carbohydrates deals with the organic and physical chemistry of the major organic constituents of living material.

This book discusses the general structure of monosaccharides, detection and estimation of aldonic acids, intramolecular rearrangement of N-glycosides, and preparation of sugar phosphates. The deacetylation of glycoside acetates, naturally occurring oligosaccharides of human milk, and molecular weight of polysaccharides are also elaborated. This text likewise covers the biogenesis and fate of pectic substances in plant tissues, complex polysaccharides of gram-positive bacteria, galactosaminoglycan of Aspergillus parasiticus, and chemical structure of heparin sulfate.

This volume is a good source for biochemists and researchers conducting work on carbohydrates.

Contenu

General Preface

Preface to Section II

Chapter I. The Monosaccharides

1. General Structure of Monosaccharides

   a. Properties of the Aldehydic and Ketonic Groups

   b. Properties of the Hydroxyl Groups

   c. Projection Formulae

2. The Configuration of Monosaccharides

   a. Aldoses

   b. Ketoses

   c. Heptoses

   d. Heptuloses

   e. Octose

3. Structurally Modified Monosaccharides

   a. Branched-Chain Sugars

   b. Deoxy-Sugars

   c. Amino-Sugars

   d. Neuraminic Acid

   e. Uronic Acids

4. The Monosaccharides as Ring Compounds

   a. Mutarotation of the Monosaccharides

   b. Glycosides

   c. Determination of the Ring Size in Monosaccharides

   d. Conformation of Pyranose Forms of Monosaccharides

5. Interconversions

   a. Pentoses to Hexoses

   b. Hexoses to Pentoses

   c. Aldoses to Ketoses

   d. Aldoses to Other Aldoses

   e. The Action of Alkali on Monosaccharides

6. Esters

7. Acetals

8. Anhydro-Sugars

9. Amino-Sugars

10. Separation and Identification of Monosaccharides

    a. Qualitative

    b. Quantitative

    Acknowledgement

    References

Chapter II. Aldonic, Uronic, Oxoaldonic and Ascorbic Acids

1. Aldonic Acids

   a. Preparation of Aldonic Acids

   b. Properties of the Aldonic Acids

   c. Detection and Estimation of Aldonic Acids

   d. Uses of Gluconic Acid

2. Uronic Acids

   a. Preparation of Uronic Acids

   b. Properties of Uronic Acids

   c. Detection and Estimation of Uronic Acids

3. Oxoaldonic Acids

   a. Preparation of Oxoaldonic Acids

   b. Properties of the Oxoaldonic Acids

   c. Determination of Oxoaldonic Acids

4. Ascorbic Acids

   a. Preparation of Ascorbic Acids

   b. Properties of Ascorbic Acids

   c. Detection and Determination of Ascorbic Acids

   d. Biological Function of Ascorbic Acid

   References

Chapter III. Amino Sugars

1. Syntheses

   a. Addition of NH3 to Sugar Epoxides

   b. Epimerization of 2-Acetamido-2-Deoxyaldoses

   c. Intramolecular Rearrangement of N-Glycosides (Amadori Rearrangement, Heyns Rearrangement)

   d. The HCN Method (Partial Hydrogenation of Aminonitriles)

   e. The Nitromethane Method

2. Derivatives

   a. Acyl Derivatives

   b. Glycosides

   c. Methyl Ethers

3. Stability, Oxidation and Decomposition Reactions

   The Morgan-Elson reaction 106

   References

Chapter IV. Sugar Phosphates

1. Introduction

2. Preparation of Sugar Phosphates

   a. Enzymic Methods

   b. Chemical Methods Applied to Natural Products

   c. Chemical Synthesis

   d. Isolation of Sugar Phosphates

3. Separation of the Phosphate Group

   a. Acid Hydrolysis

   b. Alkaline Hydrolysis

   c. Phosphate Removal by Other Procedures

4. Analytical Methods

5. Acid Strength

6. Descriptive

   a. Two-Carbon Compounds

   b. Three-Carbon Compounds

   c. Four-Carbon Compounds

   d. Five-Carbon Compounds

   e. Six-Carbon Compounds

   f. Seven-Carbon Compounds

   g. Eight-Carbon Compounds

   h. Disaccharide Phosphates

   k. Polysaccharide Phosphates

   References

Chapter V. Glycosides

1. Introduction

2. The Fischer Reaction

3. The Helferich Reaction

4. The Koenigs-Knorr Reaction

5. Deacetylation of Glycoside Acetates

6. Preparation of Glycosyluronic Acids

   References

Chapter VI. The Oligosaccharides

1 . Introduction

2. Preparation

3. Disaccharides

   a. General Properties

   b. Determination of Structure

   c. Individual Disaccharides

4. Higher Oligosaccharides

5. Oligosaccharides of Animal Origin

   a. Naturally Occurring Oligosaccharides of Human Milk

   b. Oligosaccharides Derived from Animal Polysaccharides

6. Enzymatic Synthesis of Oligosaccharides by Transglycosylation

   a. General Discussion

   b. a-Glucosyl Transfer

   c. ß-Glucosyl Transfer

   d. ß-Fructofuranosyl Transfer

   e. Galactosyl Transfer

   f. Transglucosylation from Sugar Phosphates

   g. Glycosyl Transfer from Uridylphosphoglycosyl Compounds

   References

Chapter VII. Polysaccharides

Section a. General

1. Introduction

2. Classification

Chapter VII. Polysaccharides

Section b. Polysaccharides (Excluding Glycuronans, Bacterial Polysaccharides and Mucopolysaccharides)

1. Nomenclature

2. Examination of Polysaccharides by Physical Methods

   a. Molecular Weight of Polysaccharides

   b. Other Structural Information by Physical Methods

3. Examination of Polysaccharides by Chemical Methods

   a. Isolation of Pure Polysaccharides

   b. Identification of the Monosaccharides

   c. Fragmentation Analysis

   d. Enzymic Hydrolysis

   e. Acylation and Alkylation Reactions

   f. Methylation

   g. Oxidation of Polysaccharides

   h. Alkaline Degradation of Polysaccharides

4. Homopolysaccharides

   a. Cellulose

   b. Chitin

   c. Starch

   d. Glycogen

   e. Other Glucans

   f. Mannans

   g. Galactans

   h. Fructans

   k. Pentoglycans

5. Heteropolysaccharides

   a. Heteropolysaccharides Containing Neutral Sugars Only

   b. Heteropolysaccharides Containing Uronic Acids

   Bibliography

Chapter VII. Polysaccharides

Section c. Polyuronides

1. Introduction

2. The Pectic Polyuronides (Pectins)

   a. Occurrence

   b. Definition and Nomenclature

   c. Structure

   d. Macromolecular Concepts and Heterogeneity

   e. Biogenesis and Fate of Pectic Substances in Plant Tissues

   f. Properties and Application

   g. Methods of Analysis

   h. Enzymes Acting Upon Pectic Substances

3. Alginic Acids and Alginates (Algin)

   a. Occurrence and Terminology

   b. Manufacture and Properties

   c. Structure

   d. Methods of Analysis

   e. Enzymes Acting Upon Alginates

   References

Chapter VII. Polysaccharides

Section d. Polysaccharides of Bacteria, Moulds, Yeasts and Protozoa

1. Introduction

2. Polyglucosans

   a. Crown Gall Polysaccharide

   b. Polysaccharide II

   c. Yeast Glucan

   d. Nigeran

   e. Luteose

   f. Dextran

3. Levans (Polyfructosans)

4. Polymannans

5. Polygalactans

6. Colominic Acid (Poly-N-Acetylneuraminic Acid)

7. Chitin

8. Vi Antigen (Poly-2-N-Acetamido-2-Deoxy-D-Galacturonic Acid)

9. Hyaluronic Acid

10. Complex Polysaccharides of Gram-Positive Bacteria

11. Complex Polysaccharides of Gram-Negative Bacteria

    Acknowledgement

    References

Chapter VII. Polysaccharides

Section e. Mucopolysaccharides (Acidic Glycosaminoglycans)

1. Introduction

2. Nomenclature

3. General Methods

   a. Isolation and Purification

   b. Determination of the Constituents

   c. Determination of the Chemical Structure

4. Chitin

   a. Introduction

   b. Occurrence, Detection and I…