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Malonyl carba(dethia)- and Malonyl oxa(dethia)-coenzyme A as tools for trapping polyketide intermediates
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Tosin, Manuela, Spiteller, Dieter and Spencer, Jonathan B. (2009) Malonyl carba(dethia)- and Malonyl oxa(dethia)-coenzyme A as tools for trapping polyketide intermediates. Chembiochem, Vol.10 (No.10). pp. 1714-1723. doi:10.1002/cbic.200900093 ISSN 1439-4227.
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Official URL: http://dx.doi.org/10.1002/cbic.200900093
Abstract
Caught in a trap. In this study trapped polyketide species (see figure) were off-loaded from a type III PKS by novel nonhydrolyzable malonyl coenzyme A analogues in which a methylene group or an oxygen atom replaces the sulfur atom of malonyl-CoA. This strategy allows the straightforward characterisation of intermediates of polyketide biosynthesis by LC-HR-ESI-MS/MS and provides valuable insights on the mechanism and timing of polyketide formation.
In order to study intermediates in polyketide biosynthesis two nonhydrolyzable malonyl coenzyme A analogues were synthesised by a chemoenzymatic route. In these analogues the sulfur atom of CoA was replaced either by a methylene group (carbadethia analogue) or by an oxygen atom (oxadethia analogue). These malonyl-CoA analogues were found to compete with the natural extender unit malonyl-CoA and to trap intermediates from stilbene synthase, a type III polyketide synthase (PKS). From the reaction of stilbene synthase with its natural phenylpropanoid substrates, diketide, triketide and tetraketide species were successfully off-loaded and characterised by LC-MS. Moreover, the reactivity of the nonhydrolyzable analogues offers insights into the flexibility of substrate alignment in the PKS active site for efficient malonyl decarboxylation and condensation.
Item Type: | Journal Article | ||||
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Divisions: | Faculty of Science, Engineering and Medicine > Science > Chemistry | ||||
Journal or Publication Title: | Chembiochem | ||||
Publisher: | Wiley - V C H Verlag GmbH & Co. KGaA | ||||
ISSN: | 1439-4227 | ||||
Official Date: | 2009 | ||||
Dates: |
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Volume: | Vol.10 | ||||
Number: | No.10 | ||||
Page Range: | pp. 1714-1723 | ||||
DOI: | 10.1002/cbic.200900093 | ||||
Status: | Peer Reviewed | ||||
Publication Status: | Published |
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