Synthesis and structural analysis of 6-aminobicyclo[2.2.1]heptane-2-carboxylic acid as a conformationally constrained gamma-turn mimic

Protein Pept Lett. 2008;15(9):980-4. doi: 10.2174/092986608785849380.

Abstract

An efficient asymmetric synthesis of 6-aminobicyclo[2.2.1]heptane-2-carboxylic acid as a novel gamma-turn mimic has been achieved. Structural analysis of the gamma-amino acid derivative was carried out using (1)H NMR spectroscopy and intramolecular hydrogen bonding between side chain amides confirmed the turn structure, which had been predicted by Ab initio computational study.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amino Acids, Cyclic / chemical synthesis*
  • Amino Acids, Cyclic / chemistry*
  • Bridged Bicyclo Compounds / chemical synthesis*
  • Bridged Bicyclo Compounds / chemistry*
  • Heptanes / chemistry
  • Hydrogen Bonding
  • Magnetic Resonance Spectroscopy
  • Models, Molecular
  • Molecular Mimicry
  • Molecular Structure
  • Norbornanes
  • Protein Structure, Secondary

Substances

  • 6-aminobicyclo(2.2.1)heptane-2-carboxylic acid
  • Amino Acids, Cyclic
  • Bridged Bicyclo Compounds
  • Heptanes
  • Norbornanes