Synthesis of 2-amino-3-fluoroacrylic acid containing peptides

Org Lett. 2001 Feb 22;3(4):593-6. doi: 10.1021/ol006997s.

Abstract

[reaction: see text] Peptides containing (E)- and (Z)-3-fluorodehydroalanine have been prepared from serine via a fluoro-Pummerer rearrangement. The resulting electrophilic moieties may be useful affinity labels for the identification of the targets of dehydroamino acid containing natural products that act by covalent mechanisms.

Publication types

  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.
  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Acrylates / chemical synthesis*
  • Acrylates / chemistry
  • Alanine / analogs & derivatives
  • Alanine / chemical synthesis*
  • Alanine / chemistry
  • Dipeptides / chemical synthesis*
  • Dipeptides / chemistry
  • Fluorine / chemistry
  • Molecular Structure
  • Serine / chemistry

Substances

  • 2-amino-3-fluoroacrylic acid
  • 3-fluorodehydroalanine
  • Acrylates
  • Dipeptides
  • Fluorine
  • Serine
  • Alanine