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Issue 54, 2015
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Screw sense alone can govern enantioselective extension of a helical peptide by kinetic resolution of a racemic amino acid

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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.

Graphical abstract: Screw sense alone can govern enantioselective extension of a helical peptide by kinetic resolution of a racemic amino acid

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Article information


Submitted
04 Mar 2015
Accepted
02 Jun 2015
First published
02 Jun 2015

Chem. Commun., 2015,51, 10965-10968
Article type
Communication
Author version available

Screw sense alone can govern enantioselective extension of a helical peptide by kinetic resolution of a racemic amino acid

L. Byrne, J. Solà and J. Clayden, Chem. Commun., 2015, 51, 10965
DOI: 10.1039/C5CC01790D

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