General Methods

Methods in Carbohydrate Chemistry, Volume VIII: General Methods describes the principles and mode of operation of general methods for the analysis and structural characterization of carbohydrates. This book is organized into two sections encompassing 50 chapters. The first section highlights the methods on automated chromatographic techniques; enzymic and other methods for structural analysis of polysaccharides. This section also explores the application of 13C NMR spectroscopy to carbohydrate chemistry. The second section describes the synthesis of deoxy and branched-chain sugars, 1,2-transglycosides, de-N- and de-O-sulfation, and de-N-acetylation of polysaccharides. This book is an invaluable source for organic and analytical chemists, as well as for carbohydrate scientists and researchers.

Contributors to Volume VIII

Preface

Outline of Volumes I-VII

Errata and Additions—Volumes I-VII

Section I. General Methods of Separation and Analysis

Chromatography

1. Fully Automatic Ion-Exchange Chromatographie Analysis of Neutral Monosaccharides and Oligosaccharides

2. Fully Automatic Gel-Permeation Chromatographie Analysis of Neutral Oligosaccharides

3. Separation and Automated Analysis of Phosphorylated Intermediates

4. High-Performance Liquid Chromatography

5. Gel Permeation Chromatography

6.Analysis and Structural Characterization of Amino Sugars by Gas-Liquid Chromatography and Mass Spectrometry

Analysis of Polysaccharides by Chemical, Physical, and Enzymic Methods

7. Sequential Degradation of Methylated Polysaccharides

8. Enzymic Method for Determination of Glycerol Chain Lengths of Hexans

9. Enzymic Method for Determination of the Degree of Polymerization of Glucans and Xylans

10. Enzymic Analysis of Acidic Glycosaminoglycans

11. Constituent Analysis of Glycosaminoglycans

12. Determination of Polysaccharide Structures with 13C NMR

13. Determination of the Sugar Sequence and Glycosidic Bond Arrangement of Heteroglycans by an Integrated Analytical Scheme

14. Oxidation of Acetylated Carbohydrates with Chromium Trioxide in Acetic Acid

15. Specific Cleavage of Polysaccharides Containing Uronic Acid Residues by the Hoffman-Veerman Reaction

16. Determination of Carboxymethyl Ether Groups in Sodium O-Carboxymethylcellulose(CMC)

Other Chemical, Physical, and Enzymic Methods

17. Enzymic Determination of D-Galactose

18. Enzymic Determination of D-Glucose, D-Fructose, and D-Mannose

19. Microenzymic Procedures for the Identification of Carbohydrates

20. Method for Measuring the Affinity between Carbohydrate Ligands and Certain Proteins

21. 13C NMR Spectroscopy of Isotopically Enriched Carbohydrates

Section II. Preparation of Mono-, Oligo-, and Polysaccharides and Their Derivatives

Monosaccharides and Their Derivatives

22. Methyl α-D-Altropyranoside and Its 4,6- and 3,4-O-Isopropylidene Derivatives

23. L-Gulose and Methyl ß-L-Gulofuranoside

24. L-Idose and L-Iduronic Acid

25. Applications of the 1,3-Dithiane Procedure for the Synthesis of Branched-Chain Carbohydrates L-Streptose, Methyl ß-D-Hamameloxide, Methyl 2,3,6-Trideoxy-2-C-(2-Benzoxyacetyl)-2,3,6-trideoxy-α-L-threo-hexopyranoside

26. 2,6-Dideoxy-D-ribo-hexose (Digitoxose)

27. 2,6-Dideoxy-α-L-lyxo-hexose (2-Deoxy-α-L-fucose)

28. Methoxymercuration in Synthetic Carbohydrate Chemistry Methyl 2,6-Dideoxy-α-L-arabino-hexopyranoside

Polysaccharides

29. Isolation and Purification of Carbohydrate Antigens

Unsaturated Sugars

30. 3-Deoxyglycals (1,5-Anhydro-1,2,3-trideoxyhex-1-enitols) from Hex-2-enopyranosides

Deoxyhalo Sugars

31. Preferential Halogenation of the Primary Hydroxyl Group

Glycosides and Glycosylamines

32. Complexes of Carbohydrates with Metal Cations Methyl ß-D-Mannofuranoside

33. 1,2-Orthoester Formation and Glycosidation with Amide Acetals

34. Preparation of 1,2-trans-Glycosides in the Presence of Stannic Chloride

35. Preparation of 1,2-trans-Glycosides in the Presence of Silver Trifluoromethanesulfonate

36. 1,2-trans-1-Thioglycosides

37. Primary Glycopyranosylamines

38. Production of Sugar Nucleotides by Fermentation

Esters and Amides

39. O-Chloroacetate Derivatives of Sugars as Synthetic Intermediates

40. Cyclic Thionocarbonates

41. Desulfation of Polysaccharides

42. Desulfation of Glycosaminoglycuronan Sulfates

43. De-N-sulfation

44. N-Deacetylation of Polysaccharides

45. N-Trifluoroacetylation Methyl 6-Deoxy-6-trifluoracetamido-α-D-glucopyranoside and Its N-Detrifluoroacetylation

46. Nucleophilic Reaction of the Tosyl Group in Enolic Sugar Derivatives

Ethers

47. Allyl Ethers as Protecting Groups Synthesis of 3-0-[6-O-(α-D-Galactopyranosyl)-/ß-D-galactopyranosyl]-1,2-di-O-stearoyl-L-glycerol, a "Digalactosyl Diglyceride"

Cyclic Acetals

48. Methyl 4,6-O-Benzylidene-α- and -ß-O-glucopyranosides via Acetal Exchange

49. Benzylidenation of Diols with α,α-Dihalotoluenes in Pyridine

Oxidized Products

50. Photochemical Oxidation of Carbohydrates 1,2,3,4-Di-O-isopropylidene-α-D-galacto-hexodialdo-1,5-pyranose

Glossary

Author Index

Subject Index