Chapter 11. Conformational Analysis of C-Glycosides and Related Compounds: Programming Conformational Profiles of C- and O-Glycosides

  1. Prof. Dr. Chi-Huey Wong
  1. Peter G. Goekjian,
  2. Alexander Wei,
  3. Yoshito Kishi

Published Online: 28 JAN 2005

DOI: 10.1002/3527602437.ch11

Book Title

Carbohydrate-Based Drug Discovery

Carbohydrate-Based Drug Discovery

Additional Information

How to Cite

Goekjian, P. G., Wei, A. and Kishi, Y. (2005) Conformational Analysis of C-Glycosides and Related Compounds: Programming Conformational Profiles of C- and O-Glycosides, in Carbohydrate-Based Drug Discovery (ed C.-H. Wong), Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim, FRG. doi: 10.1002/3527602437.ch11

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:

  • C- and O-glycosides;
  • conformational analysis;
  • stereoelectronic effects;
  • exo-anomeric conformation;
  • C-monoglycosides;
  • C-disaccharides;
  • syn-pentane interactions;
  • oligosaccharide conformation;
  • conformational design of C-trisaccharides;
  • human blood group trisaccharides

Summary

  • Introduction

  • Stereoelectronic Effects and the exo-Anomeric Conformation

  • Conformational Analysis of C-Glycosides: C-Monoglycosides

  • 1,4-Linked C-Disaccharides: the Importance of syn-Pentane Interactions

  • Prediction of Conformational Preference and Experimental Validation

  • Programming Oligosaccharide Conformation

  • Conformational Design of C-Trisaccharides based on a Human Blood Group Antigen

  • Conformational Design: Relationship to Biological Activity

    • C-Lactose vs. O-Lactose

    • Human Blood Group Trisaccharides

  • Concluding Remarks

  • Acknowledgements

  • References

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