Left-handed helical preference in an achiral peptide chain is induced by an L-amino acid in an N-terminal type II β-turn

J Org Chem. 2013 Mar 15;78(6):2248-55. doi: 10.1021/jo302705k. Epub 2013 Jan 22.

Abstract

Oligomers of the achiral amino acid Aib adopt helical conformations in which the screw-sense may be controlled by a single N-terminal residue. Using crystallographic and NMR techniques, we show that the left- or right-handed sense of helical induction arises from the nature of the β-turn at the N terminus: the tertiary amino acid L-Val induces a left-handed type II β-turn in both the solid state and in solution, while the corresponding quaternary amino acid L-α-methylvaline induces a right-handed type III β-turn.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amino Acids / chemistry*
  • Aminoisobutyric Acids / chemistry*
  • Circular Dichroism
  • Crystallography, X-Ray
  • Magnetic Resonance Spectroscopy
  • Models, Molecular
  • Oligopeptides / chemistry
  • Protein Conformation
  • Protein Structure, Secondary
  • Stereoisomerism
  • Valine / chemistry*

Substances

  • Amino Acids
  • Aminoisobutyric Acids
  • Oligopeptides
  • 2-aminoisobutyric acid
  • Valine