Novel chiral imidazole cyclophane receptors: synthesis and enantioselective recognition for amino acid derivatives

Chem Commun (Camb). 2001 Sep 21:(18):1816-7. doi: 10.1039/b103325p.

Abstract

Novel chiral imidazole cyclophane receptors were synthesized by highly selective N-alkylation of the imadazolyl 1N-position of the bridged histidine diester 2 with the dibromide in the presence of NaH; these receptors exhibit good chiral recognition toward the enantiomers of L- and D-amino acid derivatives (up to KD/KL = 3.52, delta delta G0 = -3.11 kJ mol-1) in CHCl3 at 25.0 degrees C.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amino Acids / chemistry*
  • Amino Acids / metabolism*
  • Histidine / chemistry
  • Histidine / metabolism
  • Imidazoles / chemical synthesis*
  • Imidazoles / metabolism*
  • Macromolecular Substances
  • Molecular Structure
  • Stereoisomerism

Substances

  • Amino Acids
  • Imidazoles
  • Macromolecular Substances
  • Histidine