Iterative, aqueous synthesis of beta3-oligopeptides without coupling reagents

J Am Chem Soc. 2006 Feb 8;128(5):1452-3. doi: 10.1021/ja057706j.

Abstract

The chemoselective synthesis of amides by decarboxylative couplings of alpha-ketoacids and isoxazolidines makes possible an iterative approach to poly-beta3-peptides. Peptide assembly occurs under aqueous conditions and requires no coupling reagents. The requisite isoxazolidine monomers are prepared in enantiopure form by a convenient two-step protocol starting from the appropriate aldehydes.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Isoxazoles / chemical synthesis
  • Isoxazoles / chemistry
  • Keto Acids / chemistry
  • Oligopeptides / chemical synthesis*
  • Water / chemistry

Substances

  • Isoxazoles
  • Keto Acids
  • Oligopeptides
  • Water