Induced axial chirality in the biphenyl core of the Calpha-tetrasubstituted alpha-amino acid residue Bip and subsequent propagation of chirality in (Bip)n/Val oligopeptides

J Am Chem Soc. 2004 Oct 13;126(40):12874-9. doi: 10.1021/ja040100v.

Abstract

In the dipeptides Boc-Bip-L-Val-OMe and Boc-Bip-D-Val-OMe, an induced axial chirality in the biphenyl core of the Bip residue, a conformationally labile, proatropoisomeric C(alpha,alpha)-disubstituted glycine, was observed by electronic CD and (1)H NMR. Chiral induction is significantly higher when the Val residue is located at the C-terminal position of Bip. An outstanding phenomenon of propagation of chirality was demonstrated to occur in the related 3(10)-helical -(Bip)n-L-Val (n = 2-6) oligopeptides by CD and vibrational CD techniques.

Publication types

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

MeSH terms

  • Amino Acids / chemistry*
  • Biphenyl Compounds / chemistry*
  • Circular Dichroism
  • Dipeptides / chemistry
  • Oligopeptides / chemical synthesis
  • Oligopeptides / chemistry*
  • Spectroscopy, Fourier Transform Infrared
  • Stereoisomerism
  • Valine / chemistry

Substances

  • Amino Acids
  • Biphenyl Compounds
  • Dipeptides
  • Oligopeptides
  • Valine