Left-handed helical preference in an achiral peptide chain is induced by an l-amino acid in an N-terminal type II β-turn

Matteo De Poli, Marta De Zotti, James Raftery, Juan A. Aguilar, Gareth A. Morris, Jonathan Clayden*

*Corresponding author for this work

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

32 Citations (Scopus)

Abstract

Oligomers of the achiral amino acid Aib adopt helical conformations in which the screw-sense may be controlled by a single N-terminal residue. Using crystallographic and NMR techniques, we show that the left- or right-handed sense of helical induction arises from the nature of the β-turn at the N terminus: the tertiary amino acid l-Val induces a left-handed type II β-turn in both the solid state and in solution, while the corresponding quaternary amino acid l-α-methylvaline induces a right-handed type III β-turn.

Original languageEnglish
Pages (from-to)2248-2255
Number of pages8
JournalJournal of Organic Chemistry
Volume78
Issue number6
Early online date22 Jan 2013
DOIs
Publication statusPublished - 15 Mar 2013

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