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Chemical probes for the functionalization of polyketide intermediates

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Riva, Elena, Wilkening, Ina, Gazzola, Silvia, Li, W. M. Ariel, Smith, Luke, Leadlay, P. F. and Tosin, Manuela (2014) Chemical probes for the functionalization of polyketide intermediates. Angewandte Chemie International Edition, 53 (44). pp. 11944-11949. doi:10.1002/anie.201407448

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Official URL: http://dx.doi.org/10.1002/anie.201407448

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Abstract

A library of functionalized chemical probes capable of reacting with ketosynthase-bound biosynthetic intermediates was prepared and utilized to explore in vivo polyketide diversification. Fermentation of ACP mutants of S. lasaliensis in the presence of the probes generated a range of unnatural polyketide derivatives, including novel putative lasalocid A derivatives characterized by variable aryl ketone moieties and linear polyketide chains (bearing alkyne/azide handles and fluorine) flanking the polyether scaffold. By providing direct information on microorganism tolerance and enzyme processing of unnatural malonyl-ACP analogues, as well as on the amenability of unnatural polyketides to further structural modifications, the chemical probes constitute invaluable tools for the development of novel mutasynthesis and synthetic biology.

Item Type: Journal Article
Subjects: Q Science > QP Physiology
Divisions: Faculty of Science, Engineering and Medicine > Science > Chemistry
Library of Congress Subject Headings (LCSH): Molecular probes, Polyketides
Journal or Publication Title: Angewandte Chemie International Edition
Publisher: Wiley
ISSN: 1433-7851
Official Date: 21 October 2014
Dates:
DateEvent
21 October 2014Published
11 September 2014Available
24 July 2014Accepted
21 July 2014Submitted
Volume: 53
Number: 44
Number of Pages: 6
Page Range: pp. 11944-11949
DOI: 10.1002/anie.201407448
Status: Peer Reviewed
Publication Status: Published
Access rights to Published version: Open Access
Funder: Biotechnology and Biological Sciences Research Council (Great Britain) (BBSRC), University of Warwick. Institute of Advanced Study (IAS), Marie Curie Intra-European Fellowship (IEF)
Grant number: BB/J007250/1 (BBSRC)
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