Comparative α-Helicity of Cyclic Pentapeptides in Water

de Araujo, Aline D., Hoang, Huy N., Kok, W. Mei, Diness, Frederik, Gupta, Praveer, Hill, Timothy A., Driver, Russell W., Price, David A., Liras, Spiros and Fairlie, David P. (2014) Comparative α-Helicity of Cyclic Pentapeptides in Water. Angewandte Chemie International Edition, 53 27: 6965-6969. doi:10.1002/anie.201310245/abstract

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Author de Araujo, Aline D.
Hoang, Huy N.
Kok, W. Mei
Diness, Frederik
Gupta, Praveer
Hill, Timothy A.
Driver, Russell W.
Price, David A.
Liras, Spiros
Fairlie, David P.
Title Comparative α-Helicity of Cyclic Pentapeptides in Water
Journal name Angewandte Chemie International Edition   Check publisher's open access policy
ISSN 1433-7851
Publication date 2014-05-14
Year available 2014
Sub-type Article (original research)
DOI 10.1002/anie.201310245/abstract
Open Access Status Not Open Access
Volume 53
Issue 27
Start page 6965
End page 6969
Total pages 5
Place of publication Weinheim, Germany
Publisher Wiley - V C H Verlag GmbH
Language eng
Abstract Helix-constrained polypeptides have attracted great interest for modulating protein-protein interactions (PPI). It is not known which are the most effective helix-inducing strategies for designing PPI agonists/antagonists. Cyclization linkers (X-1-X-5) were compared here, using circular dichroism and 2D NMR spectroscopy, for a-helix induction in simple model pentapeptides, Ac-cyclo(1,5)-[X-1-Ala-Ala-Ala-X-5]-NH2, in water. In this very stringent test of helix induction, a Lys1 -> Asp5 lactam linker conferred greatest alpha-helicity, hydrocarbon and triazole linkers induced a mix of alpha- and 3(10)-helicity, while thio-and dithioether linkers produced less helicity. The lactam-linked cyclic pentapeptide was also the most effective a-helix nucleator attached to a 13-residue model peptide.
Keyword α-Helices
Cyclische Peptide
Q-Index Code C1
Q-Index Status Confirmed Code
Grant ID FF0668733
Institutional Status UQ

Document type: Journal Article
Sub-type: Article (original research)
Collections: Official 2015 Collection
Institute for Molecular Bioscience - Publications
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Citation counts: TR Web of Science Citation Count  Cited 49 times in Thomson Reuters Web of Science Article | Citations
Scopus Citation Count Cited 54 times in Scopus Article | Citations
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Created: Thu, 22 May 2014, 20:02:05 EST by Mrs Louise Nimwegen on behalf of School of Chemistry & Molecular Biosciences