Concise synthesis of all stereoisomers of beta-methoxytyrosine and determination of the absolute configuration of the residue in callipeltin A

Org Lett. 2005 Aug 4;7(16):3585-8. doi: 10.1021/ol0513600.

Abstract

All stereoisomers of beta-methoxytyrosine (beta-OMeTyr), a stereo-undefined component of callipeltin A, were synthesized from L- and D-tyrosine. The stereochemistry of beta-OMeTyr in callipeltin A was determined to be 2R,3R by an oxidative procedure and Marfey's analysis. [structure: see text]

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Depsipeptides / chemistry*
  • Porifera / chemistry
  • Stereoisomerism
  • Tyrosine / analogs & derivatives*
  • Tyrosine / chemical synthesis
  • Tyrosine / chemistry

Substances

  • Depsipeptides
  • callipeltin A
  • Tyrosine
  • 3-methoxytyrosine