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Cytochrome P450-mediated hydroxylation is required for polyketide macrolactonization in stambomycin biosynthesis

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Song, Lijiang, Laureti, Luisa, Corre, Christophe, Leblond, Pierre, Aigle, Bertrand and Challis, Gregory L. (2014) Cytochrome P450-mediated hydroxylation is required for polyketide macrolactonization in stambomycin biosynthesis. The Journal of Antibiotics, Volume 67 (Number 1). pp. 71-76. doi:10.1038/ja.2013.119 ISSN 0021-8820.

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Official URL: http://dx.doi.org/10.1038/ja.2013.119

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Abstract

Many polyketide antibiotics contain macrolactones that arise from polyketide synthase chain release via thioesterase (TE) domain-catalyzed macrolactonization. The hydroxyl groups utilized in such macrolactonization reactions typically derive from reduction of β-ketothioester intermediates in polyketide chain assembly. The stambomycins are a group of novel macrolide antibiotics with promising anticancer activity that we recently discovered via rational activation of a silent polyketide biosynthetic gene cluster in Streptomyces ambofaciens. Here we report that the hydroxyl group utilized for formation of the macrolactone in the stambomycins is derived from cytochrome P450-catalyzed hydroxylation of the polyketide chain rather than keto reduction during chain assembly. This is a novel mechanism for macrolactone formation in polyketide antibiotic biosynthesis.

Item Type: Journal Article
Divisions: Faculty of Science, Engineering and Medicine > Science > Chemistry
Journal or Publication Title: The Journal of Antibiotics
Publisher: Nature Publishing Group
ISSN: 0021-8820
Official Date: January 2014
Dates:
DateEvent
January 2014Published
13 November 2013Available
17 October 2013Accepted
22 July 2013Submitted
Volume: Volume 67
Number: Number 1
Page Range: pp. 71-76
DOI: 10.1038/ja.2013.119
Status: Peer Reviewed
Publication Status: Published
Access rights to Published version: Restricted or Subscription Access

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