Chapter 26. Novel Enzymatic Mechanisms in the Biosynthesis of Unusual Sugars

  1. Prof. Dr. Chi-Huey Wong
  1. Alexander Wong,
  2. Xuemei He,
  3. Hung-Wen Liu

Published Online: 28 JAN 2005

DOI: 10.1002/3527602437.ch26

Book Title

Carbohydrate-Based Drug Discovery

Carbohydrate-Based Drug Discovery

Additional Information

How to Cite

Wong, A., He, X. and Liu, H.-W. (2005) Novel Enzymatic Mechanisms in the Biosynthesis of Unusual Sugars, in Carbohydrate-Based Drug Discovery (ed C.-H. Wong), Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim, FRG. doi: 10.1002/3527602437.ch26

Editor Information

  1. Ernest W. Hahn Chair in Chemistry, The Scripps Research Institute, 10550 N. Torrey Pines RoadLa Jolla, CA 92037, USA

Publication History

  1. Published Online: 28 JAN 2005
  2. Published Print: 26 AUG 2003

ISBN Information

Print ISBN: 9783527306329

Online ISBN: 9783527602438

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Keywords:

  • novel enzymatic mechanisms;
  • biosynthesis of unusual sugars;
  • biosynthesis of deoxysugars;
  • biosynthesis of branched-chain sugars;
  • epimerization reactions;
  • rearrangement of hexose skeletons

Summary

  • Introduction

  • Biosynthesis of Deoxysugars

    • Eod-Catalyzed C-O Bond-Cleavage at the C-6 Position in the Biosynthesis of 6-Deoxyhexose

      • Catalytic Mechanism of Eod

      • Stereochemical Course of Eod-Catalyzed Reactions

    • E1- and E3-Catalyzed C-O Bond-Cleavage at the C-3 Position in the Biosynthesis of Ascarylose

      • Catalytic Properties of CDP-6-Deoxy-L-Threo-D-Glycero-4-Hexulose 3-Dehydrase (E1)

      • Catalytic Properties of CDP-6-Deoxy-L-Threo-D-Glycero-4-Hexulose 3-Dehydrase Reductase (E3)

  • Formation of Radical Intermediates During E1 and E3 Catalysis

  • TylX3- and TylC1-Catalyzed C-O Bond-Cleavage at the C-2 Position in the Biosynthesis of Mycarose

    • Biochemical Characterization of Enzymes Involved in C-2 Deoxygenation

    • Mechanism of C-2 Deoxygenation

  • DesI- and DesII-Catalyzed C-O Bond-Cleavage at the C-4 Position in the Biosynthesis of Desosamine

    • Genetic Disruption of DesI and DesII Genes

    • Proposed Mechanisms for C-4 Deoxygenation

  • Biosynthesis of Aminosugars

    • C-N Bond-Formation by GlmS-Catalyzed Transamidation in the Biosynthesis of Glucosamine-6-Phosphate

      • Catalytic Properties of Glucosamine-6-Phosphate Synthetase

      • The Glutaminase Activity of Glucosamine-6-Phosphate Synthetase

      • The Synthetase Activity of Glucosamine-6-Phosphate Synthetase

    • C-N Bond Formation by TylB-Catalyzed Transamination in the Biosynthesis of Mycaminose

  • Biosynthesis of Branched-Chain Sugars

    • YerE- and YerF-Catalyzed Two-Carbon Branched-Chain Attachment in the Biosynthesis of Yersiniose A

  • Biochemical Properties and Catalytic Mechanism of YerE

  • Biochemical Properties of YerF

  • TylC3-Catalyzed One-Carbon Branched-Chain Attachment in the Biosynthesis of Mycarose

    • Biochemical Properties and Catalytic Mechanism of TylC3

  • Epimerization Reactions

    • UDP-N-acetylglucosamine 2-Epimerase-Catalyzed C-2 Epimerization in the Biosynthesis of N-Acetylmannosamine

      • Catalytic Properties of UDP-N-Acetylglucosamine 2-Epimerase

      • Mechanism of C-2 Epimerization

    • CDP-Tyvelose 2-Epimerase-Catalyzed C-2 Epimerization in the Biosynthesis of Tyvelose

      • Biochemical Properties of CDP-Tyvelose 2-Epimerase

      • Possible Mechanisms for C-2 Epimerization

      • Distinguishing Between Mechanisms Involving C-2 or C-4 Oxidation

  • Rearrangement of Hexose Skeletons: UDP-Galactopyranose Mutase-Catalyzed Biosynthesis of Galactofuranose

    • Catalytic Properties of UDP-Galactopyranose Mutase

    • Mechanism of Ring Contraction

  • Summary

  • Acknowledgements

  • References

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