Induction of unexpected left-handed helicity by an N-terminal L -amino acid in an otherwise achiral peptide chain

Robert A. Brown, Tommaso Marcelli, Matteo Depoli, Jordi Solà, Jonathan Clayden*

*Corresponding author for this work

Research output: Contribution to journalArticle (Academic Journal)peer-review

60 Citations (Scopus)

Abstract

Peptide helices containing L-amino acids are typically right-handed. Exceptions are peptide helices containing the achiral amino acids 2-aminoisobutyric acid and glycine with a single chiral amino acid at the Nterminus. These helices are left-handed when the N-terminal residue is a common tertiary proteinogenic amino acid, such as L-valine (see picture, left), but right-handed when the N-terminal residue is the quaternary amino acid L-α-methylvaline (right).

Original languageEnglish
Pages (from-to)1395-1399
Number of pages5
JournalAngewandte Chemie - International Edition
Volume51
Issue number6
Early online date3 Jan 2012
DOIs
Publication statusPublished - 6 Feb 2012

Keywords

  • circular dichroism
  • conformation analysis
  • foldamers
  • helical structures
  • peptides

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