Identification of the tirandamycin biosynthetic gene cluster from Streptomyces sp. 307-9.

Chembiochem : a European Journal of Chemical Biology
Jacob C CarlsonDavid H Sherman

Abstract

The structurally intriguing bicyclic ketal moiety of tirandamycin is common to several acyl-tetramic acid antibiotics, and is a key determinant of biological activity. We have identified the tirandamycin biosynthetic gene cluster from the environmental marine isolate Streptomyces sp. 307-9, thus providing the first genetic insight into the biosynthesis of this natural product scaffold. Sequence analysis revealed a hybrid polyketide synthase-nonribosomal peptide synthetase gene cluster with a colinear domain organization, which is entirely consistent with the core structure of the tirandamycins. We also identified genes within the cluster that encode candidate tailoring enzymes for elaboration and modification of the bicyclic ketal system. Disruption of tamI, which encodes a presumed cytochrome P450, led to a mutant strain deficient in production of late stage tirandamycins that instead accumulated tirandamycin C, an intermediate devoid of any post assembly-line oxidative modifications.

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Citations

Dec 14, 2011·Organic Letters·Ming Chen, William R Roush
Jul 23, 2011·Nature Chemistry·Jacob C CarlsonDavid H Sherman
Jul 24, 2012·Natural Product Reports·Larissa M Podust, David H Sherman
Aug 14, 2013·Proceedings of the National Academy of Sciences of the United States of America·Katrin GeislerAnne Osbourn
Sep 14, 2015·Journal of Industrial Microbiology & Biotechnology·Richard H Baltz
Nov 13, 2013·Angewandte Chemie·Hui HongPeter F Leadlay
Jul 22, 2015·Chembiochem : a European Journal of Chemical Biology·Yiguang ZhuChangsheng Zhang
Dec 21, 2010·Natural Product Reports·Amy L Lane, Bradley S Moore
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Apr 11, 2017·Chemical Reviews·Adrian T Keatinge-Clay
Sep 6, 2013·Microbiology and Molecular Biology Reviews : MMBR·Leslie Cuthbertson, Justin R Nodwell
Jul 11, 2020·International Journal of Molecular Sciences·Fanele Cabangile MnguniKhajamohiddin Syed
Jan 22, 2021·Natural Product Reports·Zhiyong Yin, Jeroen S Dickschat
Mar 13, 2021·Natural Product Reports·Xuhua Mo, Tobias A M Gulder
Dec 1, 2017·ACS Chemical Biology·Bernhard KepplingerNicholas Edward Ellis Allenby

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