Issue 8, 2008

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

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.

Graphical abstract: Cyclic tetrapeptides via the ring contraction strategy: chemical techniques useful for their identification

Article information

Article type
Paper
Submitted
10 Jan 2008
Accepted
05 Feb 2008
First published
28 Feb 2008

Org. Biomol. Chem., 2008,6, 1386-1395

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

D. A. Horton, G. T. Bourne, J. Coughlan, S. M. Kaiser, C. M. Jacobs, A. Jones, A. Rühmann, J. Y. Turner and M. L. Smythe, Org. Biomol. Chem., 2008, 6, 1386 DOI: 10.1039/B800464A

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