N-acyl glycinates as acyl donors in serine protease-catalyzed kinetic resolution of amines. Improvement of selectivity and reaction rate

Org Biomol Chem. 2008 Nov 7;6(21):3917-20. doi: 10.1039/b812089g. Epub 2008 Sep 2.

Abstract

Enzymatic kinetic resolution of aliphatic and benzylic amines leading to (S)-amides was achieved by using alkaline protease as the catalyst and N-octanoyl glycine trifluoroethyl ester as the acyl donor; enantioselectivity ranged between 4 to 244, while reaction times were dramatically shortened and ranged between 15 min to 6 h.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amines / metabolism*
  • Biocatalysis*
  • Esters / chemistry
  • Glycine / analogs & derivatives*
  • Glycine / metabolism*
  • Kinetics
  • Serine Endopeptidases / chemistry
  • Serine Endopeptidases / metabolism*
  • Stereoisomerism
  • Substrate Specificity
  • Temperature

Substances

  • Amines
  • Esters
  • Serine Endopeptidases
  • Glycine