Chemoselective and microwave-assisted synthesis of glycopeptoids

Org Lett. 2009 Nov 19;11(22):5210-3. doi: 10.1021/ol9021468.

Abstract

The chemoselective glycosylation of N-alkylaminooxy side chains with unprotected reducing sugars has proven useful for the synthesis of glycopeptides. Herein, we extend the N-alkylaminooxy strategy to the synthesis of glycopeptoids. A N-methylaminooxy submonomer was efficiently synthesized and incorporated into peptoids. Glycosylation of the peptoids proceeded chemoselectively and site-specifically at the N-methylaminooxy moieties. Employing microwave irradiation significantly increased the degree of glycosylation and shortened the reaction times.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Glycosylation
  • Microwaves*
  • Molecular Structure
  • Peptoids / chemical synthesis*
  • Peptoids / chemistry
  • Stereoisomerism

Substances

  • Peptoids