Cyclic tetrapeptides via the ring contraction strategy: chemical techniques useful for their identification |
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Authors: | Horton Douglas A Bourne Gregory T Coughlan Justin Kaiser Sonya M Jacobs Carolyn M Jones Alun Rühmann Andreas Turner Jill Y Smythe Mark L |
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Institution: | Institute for Molecular Bioscience, The University of Queensland, St. Lucia, Qld 4072, Australia. |
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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. |
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