Carbohydrates

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. α-Glucosyl Transfer

c. β-Glucosyl Transfer

d. β-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 Isolation

c. Properties

d. Composition and Chemical Structure


5. Galactosaminoglycan of Aspergillus Parasiticus


6. Hyaluronic Acid

a. Introduction

b. Occurrence, Detection and Isolation

c. Properties

d. Composition and Chemical Structure


7. Teichan (Teichuronic Acid)

a. Introduction

b. Isolation and Properties

c. Composition and Chemical Structure


8. Chondroitin 4-Sulfate

a. Introduction

b. Occurrence, Detection and Isolation

c. Properties

d. Composition and Chemical Structure


9. Chondroitin 6-Sulfate

a. Introduction

b. Properties and Chemical Structure


10. Chondroitin


11. Dermatan Sulfate

a. Introduction

b. Occurrence, Detection and Isolation

c. Properties

d. Composition and Chemical Structure


12. Heparan Sulfate

a. Introduction

b. Properties, Detection and Isolation

c. Chemical Structure


13. Heparin

a. Introduction

b. Occurrence, Detection and Isolation

c. Properties

d. Composition and Chemical Structure


14. Keratan Sulfate

a. Introduction

b. Isolation, Properties and Chemical Structure

References

Chapter VIII. Cyclitols


1. The Inositols

a. Occurrence

b. Constitution and Synthesis

c. Chemical Properties

d. Analysis


2. The Quercitols


3. The Inosamines


4. Quinic Acid and Shikimic Acid

References

Subject Index