Biosynthesis of Neocarazostatin A Reveals the Sequential Carbazole Prenylation and Hydroxylation in the Tailoring Steps
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Date
2015-12
Journal Title
Journal ISSN
Volume Title
Publisher
Chemistry & Biology
Abstract
Neocarazostatin A (NZS) is a bacterial alkaloid with
promising bioactivities against free radicals,
featuring a tricyclic carbazole nucleus with a prenyl
moiety at C-6 of the carbazole ring. Here, we report
the discovery and characterization of the biosynthetic
pathway of NZS through genome mining and
gene inactivation. The in vitro assays characterized
two enzymes: NzsA is a P450 hydroxylase and
NzsG is a new phytoene-synthase-like prenyltransferase
(PTase). This is the first reported native PTase
that specifically acts on the carbazole nucleus.
Finally, our in vitro reconstituted experiment demonstrated
a coupled reaction catalyzed by NzsG and
NzsA tailoring the NZS biosynthesis.
Description
Keywords
Neocarazostatin A (NZS), bacterial alkaloid, tricyclic carbazole nucleus, carbazole ring, prenyl moiety at C-6, Biosynthesis, Hydroxylation, Sequential, Carbazole Prenylation
Citation
Huang et al., 2015,Biosynthesis of Neocarazostatin A Reveals the Sequential Carbazole Prenylation and Hydroxylation in the Tailoring Steps Chemistry & Biology 22, 1633–1642