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

Bryden A F Le Bailly, Jonathan Clayden*

*Corresponding author for this work

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

24 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)7949-7952
Number of pages4
JournalChemical Communications
Volume50
Issue number59
Early online date5 Jan 2014
DOIs
Publication statusPublished - 28 Jul 2014

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