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

Douglas A Horton; Gregory T Bourne; Justin Couglan; Sonya M Kaiser; Carolyn Jacobs; Alun Jones; Andreas Ruhmann; Jill Y Turner; Mark L Smythe

doi:10.1039/B800464A

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

Journal article

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

Douglas A Horton, Gregory T Bourne, Justin Couglan, Sonya M Kaiser, Carolyn Jacobs, Alun Jones, Andreas Ruhmann, Jill Y Turner and Mark L Smythe

Organic & Biomolecular Chemistry, Vol.6(8), pp.1386-1395

2008

DOI: https://doi.org/10.1039/B800464A

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Abstract

Medicinal and Biomolecular Chemistry

Organic Chemistry

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.

Details

Title: Cyclic tetrapetides via the ring contraction strategy: chemical techniques useful for their identification
Authors: Douglas A Horton (Author) - University of Queensland
Gregory T Bourne (Author) - University of Queensland
Justin Couglan (Author) - University of Queensland
Sonya M Kaiser (Author) - University of Queensland
Carolyn Jacobs (Author) - University of Queensland
Alun Jones (Author) - ARC Special Research Centre for Functional and Applied Genomics
Andreas Ruhmann (Author) - University of Queensland
Jill Y Turner (Author) - Protagonist Pty. Ltd
Mark L Smythe (Author) - University of Queensland
Publication details: Organic & Biomolecular Chemistry, Vol.6(8), pp.1386-1395
Publisher: Royal Society of Chemistry (R S C) Publications
Date published: 2008
DOI: 10.1039/B800464A
ISSN: 1477-0520
Organisation Unit: School of Science and Engineering - Legacy; University of the Sunshine Coast, Queensland
Language: English
Record Identifier: 99450542902621
Output Type: Journal article

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