Rapid microwave-assisted solid-phase glycopeptide synthesis

Org Lett. 2005 Mar 3;7(5):877-80. doi: 10.1021/ol0474352.

Abstract

Coupling of glycosylated Fmoc-Thr or Fmoc-Ser with N-terminal amino acids on a resin proceeded smoothly under microwave irradiation for 20 min with much higher efficiency (98% yield per coupling) than found in more general conditions. Compared with a conventional protocol, the present method greatly reduces the time required for solid-phase glycopeptide synthesis from 4 days to 7 h, as is the case with the synthesis of Muc-1-related 20-residue glycopeptide carrying five core-2 trisaccharide chains. [structure: see text]

Publication types

  • Comparative Study
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amino Acid Sequence
  • Amino Acids / chemistry*
  • Glycopeptides / analysis
  • Glycopeptides / chemical synthesis*
  • Microwaves*
  • Molecular Sequence Data
  • Serine / chemistry
  • Threonine / chemistry

Substances

  • Amino Acids
  • Glycopeptides
  • Threonine
  • Serine