Cyclic tetrapeptides via the ring contraction strategy: Chemical techniques useful for their identification

Horton, D. A., Bourne, G. T., Coughlan, J., Kaiser, S. M., Jacobs, C. M., Jones, A., Ruhmann, A., Turner, J. Y. and Smythe, M. L. (2008) Cyclic tetrapeptides via the ring contraction strategy: Chemical techniques useful for their identification. Organic & Biomolecular Chemistry, 6 8: 1386-1395. doi:10.1039/b800464a


Author Horton, D. A.
Bourne, G. T.
Coughlan, J.
Kaiser, S. M.
Jacobs, C. M.
Jones, A.
Ruhmann, A.
Turner, J. Y.
Smythe, M. L.
Title Cyclic tetrapeptides via the ring contraction strategy: Chemical techniques useful for their identification
Journal name Organic & Biomolecular Chemistry   Check publisher's open access policy
ISSN 1477-0520
1477-0539
Publication date 2008-02-28
Sub-type Article (original research)
DOI 10.1039/b800464a
Open Access Status Not Open Access
Volume 6
Issue 8
Start page 1386
End page 1395
Total pages 10
Editor Vikki Allen
Place of publication Cambridge, United Kingdom
Publisher Royal Society of Chemistry
Language eng
Abstract Cyclic tetrapeptides are a class of natural products that have been shown to have broad ranging biological activities and good pharmacokinetic properties. In order to synthesise these highly strained compounds a ring contraction strategy had previously been reported. This strategy was further optimised and a suite of techniques, including the Edman degradation and mass spectrometry/mass spectrometry, were developed to enable characterisation of cyclic tetrapeptide isomers. An NMR solution structure of a cyclic tetrapeptide was also generated. To illustrate the success of this strategy a library of cyclic tetrapeptides was synthesised. © The Royal Society of Chemistry.
Keyword Combinatorial chemistry techniques
Cyclization
Magnetic resonance spectroscopy
molecular structure
Peptides
Cyclic
Small molecule libraries
Tandem mass spectrometry
Q-Index Code C1
Q-Index Status Provisional Code

Document type: Journal Article
Sub-type: Article (original research)
Collections: Excellence in Research Australia (ERA) - Collection
Institute for Molecular Bioscience - Publications
 
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Created: Thu, 03 Sep 2009, 10:14:55 EST by Mr Andrew Martlew on behalf of Institute for Molecular Bioscience