Premium
Induction of Unexpected Left‐Handed Helicity by an N‐Terminal L ‐Amino Acid in an Otherwise Achiral Peptide Chain
Author(s) -
Brown Robert A.,
Marcelli Tommaso,
De Poli Matteo,
Solà Jordi,
Clayden Jonathan
Publication year - 2012
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201107583
Subject(s) - peptide , amino acid , valine , glycine , stereochemistry , residue (chemistry) , amino acid residue , chemistry , peptide sequence , polypeptide chain , amino terminal , alanine , terminal (telecommunication) , biochemistry , computer science , gene , telecommunications
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 N terminus. 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).