Expanding Diversity: Modification of Linear and Cyclic Peptides by C-Glycosylation and N-Methylation

  • Florence Brunel
  • Anne-Marie Leduc
  • Sujan Singh
  • Xiaoping Tang
  • David M. Vogel
  • K. Grant Taylor
  • Arno F. Spatola
Part of the American Peptide Symposia book series (APSY, volume 7)

Abstract

The stereochemical versatility of carbohydrates provides much structural diversity and has made them useful also as peptidomimetic scaffolds [1], Just as peptides can be rendered more stable by backbone modifications including N-methylation and amide bond replacements [2], carbohydrates can likewise be stabilized by replacement of their vulnerable hemiacetal linkages. C-sugars are derivatives of carbohydrates in which the anomeric carbon is replaced by a methylene unit [3,4]. Carbohydrates are known to be involved in numerous biological processes such as cell-cell recognition [5]. Some glycoconjugate vaccines are being tested for prostate cancer [6]. C-sugars appear as very attractive substrates because of their increased stability especially against hydrolysis, but at the same time their structural and chemical properties are similar to O-glycosides [3,4]. This explains the increase of interest for C-glycosides [7]. Accordingly, we have initiated the synthesis of different pseudoglycopeptides.

Keywords

Hydrolysis HPLC Carbohydrate Amide Aldehyde 

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Copyright information

© Springer Science+Business Media Dordrecht 2001

Authors and Affiliations

  • Florence Brunel
    • 1
  • Anne-Marie Leduc
    • 1
  • Sujan Singh
    • 1
  • Xiaoping Tang
    • 1
  • David M. Vogel
    • 1
  • K. Grant Taylor
    • 1
  • Arno F. Spatola
    • 1
  1. 1.Department of Chemistry and The Institute for Molecular Diversity and Drug DesignUniversity of LouisvilleLouisvilleUSA

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