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Volume 151, Issue 8

Identification of tailoring genes involved in the modification of the polyketide backbone of rifamycin B by S699 Free

Abstract

Rifamycin B biosynthesis by S699 involves a number of unusual modification reactions in the formation of the unique polyketide backbone and decoration of the molecule. A number of genes believed to be involved in the tailoring of rifamycin B were investigated and the results confirmed that the formation of the naphthalene ring moiety of rifamycin takes place during the polyketide chain extension and is catalysed by Rif-Orf19, a 3-(3-hydroxyphenyl)propionate hydroxylase-like protein. The cytochrome P450-dependent monooxygenase encoded by is required for the conversion of the Δ12, 29 olefinic bond in the polyketide backbone of rifamycin W into the ketal moiety of rifamycin B. Furthermore, Rif-Orf3 may be involved in the regulation of rifamycin B production, as its knock-out mutant produced about 40 % more rifamycin B than the wild-type. The work also revealed that many of the genes located in the cluster are not involved in rifamycin biosynthesis, but might be evolutionary remnants carried over from an ancestral lineage.

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Keyword(s): ACP, acyl carrier protein , AHBA, 3-amino-5-hydroxybenzoic acid , DMDARS, 27-O-demethyl-25-O-desacetylrifamycin S , DMDARSV, 27-O-demethyl-25-O-desacetylrifamycin SV , DMRSV, 27-O-demethylrifamycin SV , ESI-MS, electrospray ionization mass spectrometry , hygR, hygromycin-resistance gene , MCS, multiple cloning site , NRPS, non-ribosomal peptide synthetase and PKS, polyketide synthase
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2005-08-01
2024-04-24
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Identification of tailoring genes involved in the modification of the polyketide backbone of rifamycin B by Amycolatopsis mediterranei S699
Microbiology 151, 2515 (2005); https://doi.org/10.1099/mic.0.28138-0
/content/journal/micro/10.1099/mic.0.28138-0
/content/journal/micro/10.1099/mic.0.28138-0
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