Deciphering the Origin and Formation of Aminopyrrole Moiety in Kosinostatin Biosynthesis

Hu, Yu; Zhou, Qiang; Zhang, Zhuan; Pan, Hai‐Xue; Ilina, Yulia; Metsä‐Ketelä, Mikko; Igarashi, Yasuhiro; Tang, Gong‐Li

doi:10.1002/cjoc.202100525

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References 34 publications

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“…TP‐A0468 (M‐ rif , Figure 1A) in our biosynthetic study of kosinostatin. [ 8‐9 ] The biosynthesis of 16‐demethyl‐ rifamycins in Micromonospora sp. TP‐A0468 was investigated to verify rifamycin biosynthetic pathway and seek answers for undetermined questions.…”

Section: Background and Originality Contentmentioning

confidence: 99%

Characterizing Post‐PKS Modifications of 16‐Demethyl‐rifamycin Revealed Two Dehydrogenases Diverting the Aromatization Mode of Naphthalenic Ring in Ansamycin Biosynthesis

et al. 2022

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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.

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Section: Background and Originality Contentmentioning

confidence: 99%