title: Screw sense alone can govern enantioselective extension of a helical peptide by kinetic resolution of a racemic amino acid.
abstract: Helical peptides built principally from the achiral quaternary amino acid Aib but with an induced preferred screw-sense exhibit enantioselectivity in their chain-extension reactions when presented with a racemic tertiary amino acid. This is the first demonstration that secondary structure alone, in the absence of local chiral residues, can direct the enantioselectivity of peptide coupling.
authors.affiliation: School of Chemistry, University of Manchester, Oxford Road, Manchester M13 9PL, UK. clayden@man.ac.uk.
authors.forename: Liam
authors.initials: L
authors.lastname: Byrne
authors.forename: Jordi
authors.initials: J
authors.lastname: Solà
authors.forename: Jonathan
authors.initials: J
authors.lastname: Clayden
mesh_terms: D000596:Amino Acids / Q000737:chemistry* / Q000378:metabolism; D000621:Aminoisobutyric Acids / Q000737:chemistry; D002942:Circular Dichroism; D007700:Kinetics; D009682:Magnetic Resonance Spectroscopy; D010455:Peptides / Q000737:chemistry* / Q000378:metabolism; D017433:Protein Structure, Secondary; D013237:Stereoisomerism
chemical_list: D000596:Amino Acids; D000621:Aminoisobutyric Acids; D010455:Peptides; C100049:2-aminoisobutyric acid