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Coexistence of hydrogen-bonded loop and extended tetrapeptide conformations


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.

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.

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.

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Additional indexing

Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Uncontrolled Keywords:General Chemistry
Language:English
Date:2007
Deposited On:20 Oct 2011 12:25
Last Modified:18 Aug 2018 00:57
Publisher:Wiley-Blackwell
ISSN:0947-6539
Funders:Swiss National Science Foundation (SNF grant 200020-107492), Alfred-Werner Legat, Universität Zürich
OA Status:Closed
Publisher DOI:https://doi.org/10.1002/chem.200700396
PubMed ID:17696185
Project Information:
  • : FunderSNSF
  • : Grant ID
  • : Project TitleSwiss National Science Foundation (SNF grant 200020-107492)
  • : Funder
  • : Grant ID
  • : Project TitleAlfred-Werner Legat, Universität Zürich

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