An improved protocol for the preparation of (S)-vinylglycine from (S)-methionine

Amino Acids. 2010 Jul;39(2):443-8. doi: 10.1007/s00726-009-0460-3. Epub 2010 Jan 27.

Abstract

We present an optimized procedure for the synthesis of (S)-vinylglycine from (S)-methionine. The key step is a solvent free pyrolysis of an intermediate sulfoxide at high temperature. Using our optimized reaction conditions, Cbz-protected vinylglycine was obtained in high yield and with almost no side products. The protocol is scalable, fast and avoids the use of poisonous reagents.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Glycine / analogs & derivatives*
  • Glycine / chemical synthesis
  • Methionine / chemistry*
  • Stereoisomerism

Substances

  • vinylglycine
  • Methionine
  • Glycine