Poly-L-proline type II peptide mimics based on the 3-azabicyclo[3.1.0]hexane system

J Org Chem. 2001 Jan 26;66(2):455-60. doi: 10.1021/jo001201o.

Abstract

This paper describes conformational studies of proline-templated amino acids (PTAAs) based on the 3-azabicyclo[3.1.0]hexane system as well as conformational studies on short peptides composed of these PTAAs. NOE data, coupling constants, and molecular modeling are consistent with a flattened boat conformation for monomeric and oligomeric residues based on this bicyclic system. NMR studies on dimeric and trimeric oligomers are consistent with a populated poly-L-proline type II conformation in CDCl3 and D2O. Solution studies and molecular modeling predicts phi approximately -70 degrees, psi approximately 131 degrees, chi 1 approximately -57 degrees, and chi 2 approximately -158 degrees for oligomeric residues.

Publication types

  • Research Support, U.S. Gov't, Non-P.H.S.
  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Bridged Bicyclo Compounds, Heterocyclic / chemical synthesis*
  • Bridged Bicyclo Compounds, Heterocyclic / chemistry*
  • Dimerization
  • Indicators and Reagents
  • Molecular Conformation
  • Molecular Structure
  • Peptides / chemistry*
  • Proline*
  • Protein Conformation
  • Structure-Activity Relationship

Substances

  • Bridged Bicyclo Compounds, Heterocyclic
  • Indicators and Reagents
  • Peptides
  • polyproline
  • Proline