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- Title
Characterizing Post‐PKS Modifications of 16‐Demethyl‐rifamycin Revealed Two Dehydrogenases Diverting the Aromatization Mode of Naphthalenic Ring in Ansamycin Biosynthesis.
- Authors
Han, Ting‐Yan; Zhang, Kai; Tang, Gong‐Li; Zhou, Qiang
- Abstract
Comprehensive Summary: The anti‐tuberculous rifamycins belong to naphthalenic ansamycin based on the structure of aromatic chromophore. Herein, we explored the post‐polyketide synthase (PKS) modifications in the biosynthesis of 16‐demethyl‐rifamycins via gene knockout, complementation and in vitro enzyme assays. The collective evidences showed that i) the aromatization of 8‐hydroxyl‐7,8‐dihydronaphtoquinone was accomplished by the combined action of two dehydrogenases, RifS and RifT; ii) the acetylation and methylation of the macrocycle was carried out on naphthoquinone intermediates in preference to naphthol, by Rif‐Orf20 and Rif‐Orf14, respectively; iii) the presence of RifS/T homologs in ansamycin biosynthetic gene clusters corresponds to the dehydrogenation aromatization mode of dihydronaphthalene. These findings cast new insights into the naphthalene formation and post‐PKS modification of ansamycins.
- Subjects
AROMATIZATION; DEHYDROGENASES; BIOSYNTHESIS; GENE knockout; GENE clusters; RIFAMYCINS
- Publication
Chinese Journal of Chemistry, 2022, Vol 40, Issue 13, p1553
- ISSN
1001-604X
- Publication type
Article
- DOI
10.1002/cjoc.202200098