Efficient microwave-assisted tandem N- to S-acyl transfer and thioester exchange for the preparation of a glycosylated peptide thioester

Org Lett. 2006 Sep 28;8(20):4465-8. doi: 10.1021/ol0616034.

Abstract

A peptide carrying a mercaptomethylated proline derivative at the C-terminus was prepared by solid-phase peptide synthesis (SPPS) and converted to the thioester of 3-mercaptopropionic acid (MPA) by aqueous MPA under microwave irradiation conditions. This post-SPPS thioesterification reaction was successfully applied to the synthesis of a glycopeptide thioester composed of 25 amino acid (AA) residues, which was then used for the preparation of a 61-AA glycopeptide by the thioester condensation method.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • 3-Mercaptopropionic Acid / chemistry
  • Chromatography, High Pressure Liquid
  • Esters / chemistry*
  • Glycosylation
  • Microwaves*
  • Oxidation-Reduction
  • Peptides / chemical synthesis*
  • Peptides / chemistry
  • Sulfhydryl Compounds

Substances

  • Esters
  • Peptides
  • Sulfhydryl Compounds
  • 3-Mercaptopropionic Acid