Enantioselective chromenone benzoxazole receptor for glutamic acid and its derivatives

J Org Chem. 2003 Sep 19;68(19):7513-6. doi: 10.1021/jo0347157.

Abstract

Combination of a binaphthyl unit with chromenone benzoxazole fragments provided a chiral receptor that is enantioselective for glutamic acid and its derivatives. The receptor racemic mixture was resolved by TLCs impregnated with (R,R)-thiodilactic acid. High association constants were measured for dansylglutamic acid, using a fluorescent method. This receptor can be used for the resolution of the tosylglutamic acid racemic mixture.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Benzoxazoles / chemistry*
  • Dansyl Compounds / chemistry
  • Glutamates / chemistry
  • Glutamic Acid / analogs & derivatives*
  • Models, Molecular
  • Molecular Mimicry
  • Molecular Structure
  • Receptors, Glutamate / chemistry*
  • Stereoisomerism

Substances

  • Benzoxazoles
  • Dansyl Compounds
  • Glutamates
  • Receptors, Glutamate
  • Glutamic Acid
  • dansylglutamic acid