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Permanent URL to this publication: http://dx.doi.org/10.5167/uzh-50025

Cervetto, V; Pfister, R; Kolano, C; Bregy, A; Heimgartner, H; Helbing, J (2007). Coexistence of hydrogen-bonded loop and extended tetrapeptide conformations. Chemistry - A European Journal, 13(32):9004-9011.

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Abstract

The conformations of a protected tetrathiopeptide have been analysed by isotope labelling and two-dimensional infrared spectroscopy (2DIR). It has been found that Boc-Ala-Gly(=S)-Ala-Aib-OMe in acetonitrile, as well as its oxopeptide analogue, can adopt a hydrogen-bonded loop conformation in coexistence with less restricted structures. The two types of conformations interconvert too quickly to be resolved on the nuclear magnetic resonance
(NMR) timescale, but give rise to different cross peaks in two-dimensional infrared spectra. The hydrogen bond between the Boc terminal group and the amide proton of Aib can be broken by photoisomerisation of the thioamide bond.

Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
DDC:540 Chemistry
Language:English
Date:2007
Deposited On:20 Oct 2011 12:25
Last Modified:04 Jul 2014 06:57
Publisher:Wiley-Blackwell
ISSN:0947-6539
Funders:Swiss National Science Foundation (SNF grant 200020-107492), Alfred-Werner Legat, Universität Zürich
Publisher DOI:10.1002/chem.200700396
PubMed ID:17696185
Citations:Web of Science®. Times Cited: 9
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Scopus®. Citation Count: 9

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