UZH-Logo

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.

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.

Citations

9 citations in Web of Science®
9 citations in Scopus®
Google Scholar™

Altmetrics

Downloads

3 downloads since deposited on 20 Oct 2011
0 downloads since 12 months
Detailed statistics

Additional indexing

Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Language:English
Date:2007
Deposited On:20 Oct 2011 12:25
Last Modified:05 Apr 2016 15:02
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
Permanent URL: http://doi.org/10.5167/uzh-50025

Download

[img]
Content: Published Version
Filetype: PDF - Registered users only
Size: 653kB
View at publisher

TrendTerms

TrendTerms displays relevant terms of the abstract of this publication and related documents on a map. The terms and their relations were extracted from ZORA using word statistics. Their timelines are taken from ZORA as well. The bubble size of a term is proportional to the number of documents where the term occurs. Red, orange, yellow and green colors are used for terms that occur in the current document; red indicates high interlinkedness of a term with other terms, orange, yellow and green decreasing interlinkedness. Blue is used for terms that have a relation with the terms in this document, but occur in other documents.
You can navigate and zoom the map. Mouse-hovering a term displays its timeline, clicking it yields the associated documents.

Author Collaborations