A novel synthesis of enantiomerically pure 5,5,5,5',5',5'-hexafluoroleucine

Org Lett. 2001 May 3;3(9):1285-6. doi: 10.1021/ol015567e.

Abstract

[reaction in text] A novel, short, and efficient synthesis of (S)-5,5,5,5',5',5'-hexafluoroleucine (6) in greater than 99% ee starting from the protected oxazolidine aldehyde 1 is described. The enantiomeric excess of the product was calculated from an NMR analysis of a dipeptide formed by reaction with a protected L-serine derivative. Furthermore, a racemic sample of N-acylated hexafluoroleucine was enzymatically resolved by treatment with porcine kidney acylase I and was found to have the same optical rotation as a synthetic sample of 6.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amidohydrolases / metabolism
  • Dipeptides / analysis
  • Leucine / analogs & derivatives
  • Leucine / chemical synthesis*
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Serine / chemistry
  • Stereoisomerism
  • Thymidine / analogs & derivatives
  • Thymidine / chemical synthesis*
  • Thymidine / chemistry

Substances

  • 2-(N-formyl-N-methyl)aminoethyl deoxythymdine phosphoramidite
  • 5,5,5,5',5',5'-hexafluoroleucine
  • Dipeptides
  • Serine
  • Amidohydrolases
  • aminoacylase I
  • Leucine
  • Thymidine