A concise, asymmetric synthesis of (2R,3R)-3-hydroxyaspartic acid

Amino Acids. 2008 Aug;35(2):507-10. doi: 10.1007/s00726-007-0595-z. Epub 2007 Oct 3.

Abstract

3-Hydroxyaspartic acid and its derivatives are found both in the free form and as peptide constituents in various microorganisms and fungi. Considering the biological importance of this amino acid and its potential utility as a multifunctional building block in organic syntheses, we have developed a short-step, asymmetric synthetic route to a strategically protected 3-hydroxyaspartic acid derivative in enantiopure form. The key steps in the synthesis involve, Sharpless asymmetric aminohydroxylation of commercially available trans-ethyl cinnamate, and, utilization of the phenyl group as a masked carboxylic acid synthon towards construction of the complete structural framework of the title compound.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amination
  • Aspartic Acid / analogs & derivatives
  • Aspartic Acid / chemical synthesis
  • Aspartic Acid / chemistry
  • Cinnamates / chemistry
  • Hydroxylation
  • Molecular Structure
  • Stereoisomerism

Substances

  • Cinnamates
  • 3-hydroxyaspartic acid
  • Aspartic Acid
  • ethyl cinnamate