Methods in Carbohydrate Chemistry, Volume VI: General Carbohydrate Methods contains a collection of selected methods from the entire field of carbohydrate chemistry.

This volume is comprised of useful procedures in analytical and preparative carbohydrate chemistry. It is organized into 10 sections. The first section deals with methods for separation and analysis, which discusses chromatography and chemical, physical, and biochemical methods. Section II covers the preparation of mono- and polysaccharides and their derivatives. Section III describes a variety of oxidation methods. The fourth section is about procedures for the analysis of acyclic sugars. Sections V and VI present the etherification and esterification of carbohydrates. Nucleotides, nucleosides, and glycoside procedures are described in Sections VII and VIII. The ninth section focuses on radioactively labeled sugars. The final chapter provides a variety of physical methods such as mass spectrometry, nuclear magnetic resonance spectroscopy, and determination of molecular weights by osmometry.

Chemists and biochemists will find this book very useful.

Contenu

Contributors to Volume VI

Preface

Outline of Volumes I-V

Errata and Additions-Volumes I-V

Section I. Separation and Analysis

Chromatography

Gas-Liquid Chromatography of Trimethylsilyl Derivatives
Gas Chromatographie Estimation of Carbohydrates in Glycosphingolipids
Gas-Liquid Chromatography of Trimethylsilyl Ethers of Cyclitols
Gas-Liquid Chromatography of Alditol Acetates
Gas-Liquid Chromatography of Methylated Sugars
Qualitative Thin-Layer Chromatography
Quantitative Thin-Layer Chromatography
Preparative Thin-Layer Chromatography
Partition Chromatography on Ion-Exchange Resins
Chemical, Physical, and Biochemical Methods
Determination of Carbonyl Groups with Sodium Cyanide
Determination of Carbonyl Groups in Oxidized Cellulose
Direct Spectrophotometric Determination of Iodate Following Periodate Oxidation of a-Glycol Groups
Determination of Formic Acid in the Periodate Oxidation of Carbohydrates
Determination of Starch with Glucoamylase
Use of Concanavalin A for Structural Studies

Section II. Preparation of Mono- and Polysaccharides and their Derivatives

Monosaccharides

ß-D-Allose
D-Gulose
Aldohexofuranoses
Migration of Epoxide Rings and Stereoselective Ring Opening of Acetoxyepoxides
Acetoxonium Ion Rearrangements
Application of the Wittig Reaction to the Synthesis of Higher Sugars
Polysaccharides
Isolation of Polysaccharides from Gram-Negative Bacteria
Lipopolysaccharides
Teichoic Acids
Deoxy Sugars
5-Deoxy-D-xylo-Hexose
6-Deoxy-D-Glucose (D-Quinovose)
Deoxyhalo Sugars
Bromodeoxy Sugars from Epoxides
Methyl 4-O-Benzoyl-6-Bromo-6-Deoxyhexopyranosides
Chlorodeoxy Sugars via (Chloromethylene)-Dimethyliminium Chloride Reactions
6-Chloro-6-Deoxy-a-D-Glucose
Deoxyfluoro Sugars via Displacement of Sulfonyloxy Groups with Tetrabutylammonium Fluoride
Deoxyfluoro Sugars from Epoxides
Substitution of Hydroxyl Groups with Iodine
Aminodeoxy Sugars
Regeneration of Amino Functions from Acetamidodeoxy Sugars
Displacement of the p-Tolylsulfonyloxy Group in 1,2:5,6-Di-O-Isopropylidene-3-0-p-Tolylsulfonyl-a-D-Glucofuranose
Amino Sugars via Reduction of Azides
Synthesis of Amino Sugars with Retention
Amino Sugars via Displacement of Sulfonyloxy Groups with Hydrazine
Synthesis of Amino Sugars via Oximes
Amino Sugars via Anhydro Ring Opening with Ammonia
Amino Sugars via Nitroolefins
Methyl 3-Deoxy-3-Nitrohexopyranosides
Amino Sugars and Amino Cyclitols via Cyclization of Dialdehydes with Nitromethane
Synthetic Approaches to cis-Diamino Sugars
2,3-Diamino-2,3-Dideoxy-a-D-Glucose
2,6-Diamino-2,6-Dideoxy-a-D-Galactose
2,6-Diamino-2,6-Dideoxy-ß-D-Mannose
Preparation of Aminomercapto Furanose Sugars from Dithiocarbamoyl Derivatives
2-Acetamido-3,4,6-Tri-O-Acetyl-2-Deoxy-a-D-Glucopyranosyl Chloride
Thio Sugars
5-Thio-a-D-Glucopyranose
4-Thio-D-Ribofuranose
Unsaturated Sugars
Unsaturated Sugars via Cyclic Thionocarbonates, Cyclic Orthoformates, and Disulfonic Ester Intermediates
2,3-Unsaturated 3-Nitro Glycosides
Modified Synthesis of 1-Deoxyald-1-Enopyranose (2-Hydroxyglycal) Esters

Section III. Oxidation

Oxidation of Carbohydrates by the Sulfoxide-Carbodiimide and Related Methods
Oxidation of Carbohydrates with Dimethyl Sulfoxide-Acetic Anhydride
Synthesis of a Ketose from a Partially Benzylated Aldose
Oxidation of Carbohydrates with Dimethyl Sulfoxide-Phosphorus Pentaoxide
Oxidation with Ruthenium Dioxide and Hypochlorite
Selective Catalytic Oxidations of Carbohydrates
Unsaturated Glycopyranosiduloses
Oxidation of Polysaccharides with Lead Tetraacetate in Dimethyl Sulfoxide

Section IV. Acyclic Sugars

1,1-Bis(acylamido)-1-Deoxyalditols

Section V. Etherification

Methylation of Carbohydrates with Methylsulfinyl Anion and Methyl Iodide in Dimethyl Sulfoxide
Methylation with Diazomethane-Boron Trifluoride Etherate
Benzyl Ethers: Formation and Removal
2,3,4,6-Tetra-O-Benzyl-a-D-glucopyranose
Alkylation of Monosaccharides Using Sodium Hydride
C-4 Substitution of Methyl D-Glucosides and Malto-Oligosaccharides
O-Carboxymethylpachyman

Section VI. Esterification

Phosphate Esters

Glycosyl Phosphates
L-glycero-Tetrulose (L-Erythrulose) 1-Phosphate
D-altro-Heptulose (D-Sedoheptulose) 7-Phosphate
1L-myo-Inositol 1-Phosphate
Phosphorylation of Starch and Cellulose with an Amine Salt of Tetrapolyphosphoric Acid
Other Esters
1,2,3,4-Tetra-O-acetyl-ß-D-Glucopyranose and Methyl 2,3,4-Tri-0-acetyl-ß-D-Glucopyranoside
Use of Xanthates in Synthetic Carbohydrate Chemistry
Applications of Phenylboronic Acid in Carbohydrate Chemistry
Sulfation of Polysaccharides

Section VII. Nucleosides and Nucleotides