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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
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 | ||||||||||
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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: |
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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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