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Issue 59, 2014
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Controlling the sign and magnitude of screw-sense preference from the C-terminus of an achiral helical foldamer

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Abstract

The global screw-sense preference of an achiral helical oligomer may be controlled by a single chiral monomer located at one terminus. Remarkably, maximal control is induced in oligomers of the achiral quaternary amino acid Aib by a single C-terminal alaninamide residue, probably because the Ala side chain, though small, is compatible with a 310 helical conformation. The presence or absence of a C-terminal hydrogen bond donor determines the screw sense of the entire oligomer.

Graphical abstract: Controlling the sign and magnitude of screw-sense preference from the C-terminus of an achiral helical foldamer

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Article information


Submitted
01 May 2014
Accepted
05 Jun 2014
First published
05 Jun 2014

Chem. Commun., 2014,50, 7949-7952
Article type
Communication
Author version available

Controlling the sign and magnitude of screw-sense preference from the C-terminus of an achiral helical foldamer

B. A. F. Le Bailly and J. Clayden, Chem. Commun., 2014, 50, 7949
DOI: 10.1039/C4CC03261F

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