General carbohydrate method

1st Edition - January 28, 1972
Editor: Roy Whistler
Language: English
eBook ISBN:
9 7 8 - 0 - 3 2 3 - 1 4 4 2 4 - 7

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

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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.

Contributors to Volume VI

Preface

Outline of Volumes I-V

Errata and Additions—Volumes I-V

Section I. Separation and Analysis

Chromatography

1. Gas-Liquid Chromatography of Trimethylsilyl Derivatives

2. Gas Chromatographie Estimation of Carbohydrates in Glycosphingolipids

3. Gas-Liquid Chromatography of Trimethylsilyl Ethers of Cyclitols

4. Gas-Liquid Chromatography of Alditol Acetates

5. Gas-Liquid Chromatography of Methylated Sugars

6. Qualitative Thin-Layer Chromatography

7. Quantitative Thin-Layer Chromatography

8. Preparative Thin-Layer Chromatography

9. Partition Chromatography on Ion-Exchange Resins

Chemical, Physical, and Biochemical Methods

10. Determination of Carbonyl Groups with Sodium Cyanide

11. Determination of Carbonyl Groups in Oxidized Cellulose

12. Direct Spectrophotometric Determination of Iodate Following Periodate Oxidation of α-Glycol Groups

13. Determination of Formic Acid in the Periodate Oxidation of Carbohydrates

14. Determination of Starch with Glucoamylase

15. Use of Concanavalin A for Structural Studies

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

Monosaccharides

16. β-D-Allose

17. D-Gulose

18. Aldohexofuranoses

19. Migration of Epoxide Rings and Stereoselective Ring Opening of Acetoxyepoxides

20. Acetoxonium Ion Rearrangements

21. Application of the Wittig Reaction to the Synthesis of Higher Sugars

Polysaccharides

22. Isolation of Polysaccharides from Gram-Negative Bacteria

23. Lipopolysaccharides

24. Teichoic Acids

Deoxy Sugars

25. 5-Deoxy-D-xylo-Hexose

26. 6-Deoxy-D-Glucose (D-Quinovose)

Deoxyhalo Sugars

27. Bromodeoxy Sugars from Epoxides

28. Methyl 4-O-Benzoyl-6-Bromo-6-Deoxyhexopyranosides

29. Chlorodeoxy Sugars via (Chloromethylene)-Dimethyliminium Chloride Reactions

30. 6-Chloro-6-Deoxy-α-D-Glucose

31. Deoxyfluoro Sugars via Displacement of Sulfonyloxy Groups with Tetrabutylammonium Fluoride

32. Deoxyfluoro Sugars from Epoxides

33. Substitution of Hydroxyl Groups with Iodine

Aminodeoxy Sugars

34. Regeneration of Amino Functions from Acetamidodeoxy Sugars

35. Displacement of the p-Tolylsulfonyloxy Group in 1,2:5,6-Di-O-Isopropylidene-3-0-p-Tolylsulfonyl-α-D-Glucofuranose

36. Amino Sugars via Reduction of Azides

37. Synthesis of Amino Sugars with Retention

38. Amino Sugars via Displacement of Sulfonyloxy Groups with Hydrazine

39. Synthesis of Amino Sugars via Oximes

40. Amino Sugars via Anhydro Ring Opening with Ammonia

41. Amino Sugars via Nitroolefins

42. Methyl 3-Deoxy-3-Nitrohexopyranosides

43. Amino Sugars and Amino Cyclitols via Cyclization of Dialdehydes with Nitromethane

44. Synthetic Approaches to cis-Diamino Sugars

45. 2,3-Diamino-2,3-Dideoxy-α-D-Glucose

46. 2,6-Diamino-2,6-Dideoxy-α-D-Galactose

47. 2,6-Diamino-2,6-Dideoxy-β-D-Mannose

48. Preparation of Aminomercapto Furanose Sugars from Dithiocarbamoyl Derivatives

49. 2-Acetamido-3,4,6-Tri-O-Acetyl-2-Deoxy-α-D-Glucopyranosyl Chloride

Thio Sugars

50. 5-Thio-α-D-Glucopyranose

51. 4-Thio-D-Ribofuranose

Unsaturated Sugars

52. Unsaturated Sugars via Cyclic Thionocarbonates, Cyclic Orthoformates, and Disulfonic Ester Intermediates

53. 2,3-Unsaturated 3-Nitro Glycosides

54. Modified Synthesis of 1-Deoxyald-1-Enopyranose (2-Hydroxyglycal) Esters

Section III. Oxidation

55. Oxidation of Carbohydrates by the Sulfoxide-Carbodiimide and Related Methods

56. Oxidation of Carbohydrates with Dimethyl Sulfoxide-Acetic Anhydride

57. Synthesis of a Ketose from a Partially Benzylated Aldose

58. Oxidation of Carbohydrates with Dimethyl Sulfoxide-Phosphorus Pentaoxide

59. Oxidation with Ruthenium Dioxide and Hypochlorite

60. Selective Catalytic Oxidations of Carbohydrates

61. Unsaturated Glycopyranosiduloses

62. Oxidation of Polysaccharides with Lead Tetraacetate in Dimethyl Sulfoxide

Section IV. Acyclic Sugars

63. 1,1-Bis(acylamido)-1-Deoxyalditols

Section V. Etherification

64. Methylation of Carbohydrates with Methylsulfinyl Anion and Methyl Iodide in Dimethyl Sulfoxide

65. Methylation with Diazomethane-Boron Trifluoride Etherate

66. Benzyl Ethers: Formation and Removal

67. 2,3,4,6-Tetra-O-Benzyl-α-D-glucopyranose

68. Alkylation of Monosaccharides Using Sodium Hydride

69. C-4 Substitution of Methyl D-Glucosides and Malto-Oligosaccharides

70. O-Carboxymethylpachyman

Section VI. Esterification

Phosphate Esters

71. Glycosyl Phosphates

72. L-glycero-Tetrulose (L-Erythrulose) 1-Phosphate

73. D-altro-Heptulose (D-Sedoheptulose) 7-Phosphate

74. 1L-myo-Inositol 1-Phosphate

75. Phosphorylation of Starch and Cellulose with an Amine Salt of Tetrapolyphosphoric Acid

Other Esters

76. 1,2,3,4-Tetra-O-acetyl-β-D-Glucopyranose and Methyl 2,3,4-Tri-0-acetyl-β-D-Glucopyranoside

77. Use of Xanthates in Synthetic Carbohydrate Chemistry

78. Applications of Phenylboronic Acid in Carbohydrate Chemistry

79. Sulfation of Polysaccharides

Section VII. Nucleosides and Nucleotides

80. Isolation of Sugar Nucleotides

81. Pyrimidine Nucleosides by the Trimethylsilyl Method

82. Purine Nucleosides by the Trimethylsilyl Method

83. The Hilbert-Johnson Synthesis of Pyrimidine Nucleosides

84. Selective Phosphorylation of Ribonucleosides

Section VIII. Glycosides

85. Cerebrosides, Isolation

86. Gangliosides, Isolation

87. Use of Mercuric Cyanide and Mercuric Bromide in the Koenigs-Knorr Reaction

88. Synthesis of Oligosaccharides by the Orthoester Method

89. cis-1,2-Glycosides

Section IX. Radioactively Labeled Sugars

90. Preparation of Tritiated Sugars

91. Degradation and Counting of Tritium-Containing Sugars

Section X. Physical Methods

92. Determination of Molecular Weights Osmometry

93. Conformational Analysis via Nuclear Magnetic Resonance Spectroscopy

94. Mass Spectrometry of Carbohydrates

Glossary

Author Index

Subject Index