Chemoselective Staudinger-phosphite reaction of symmetrical glycosyl-phosphites with azido-peptides and polygycerols

Org Biomol Chem. 2012 Aug 14;10(30):6211-6. doi: 10.1039/c2ob25207d. Epub 2012 Jun 12.

Abstract

In this paper we present the synthesis of glyco-phosphoramidate conjugates as easily accessible analogs of glyco-phosphorous esters via the Staudinger-phosphite reaction. This protocol takes advantage of synthetically accessible symmetrical carbohydrate phosphites in good overall yields, in which ethylene or propylene linkers can be introduced between phosphorous and galactose or lactose moieties. The phosphites were finally applied for the chemoselective reaction with azido-peptides and polyazido(poly)glycerols.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Azides / chemistry*
  • Dendrites / chemistry
  • Glycerol / chemistry*
  • Glycopeptides / chemical synthesis
  • Glycopeptides / chemistry*
  • Phosphites / chemistry*
  • Stereoisomerism
  • Substrate Specificity

Substances

  • Azides
  • Glycopeptides
  • Phosphites
  • Glycerol