期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 134, 期 30, 页码 12434-12437出版社
AMER CHEMICAL SOC
DOI: 10.1021/ja305670f
关键词
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资金
- NIH [AI47818]
- LSRF via a Merck postdoctoral fellowship
- DAAD
- JNC Corp.
Axially chiral biaryl compounds are frequently encountered in nature where they exhibit diverse biological properties. Many are biphenols that have C-C or C-O linkages installed by cytochrome P450 oxygenases that control the regio- and stereoselectivity of the intermolecular coupling reaction. In contrast, bipyrrole-coupling enzymology has not been observed. Marinopyrroles, produced by a marine-derived streptomycete, are the first 1,3'-bipyrrole natural products. On the basis of marinopyrrole's unusual bipyrrole structure, we explored its atropo-selective biosynthesis in Streptomyces sp. CNQ-418 in order to elucidate the N,C-bipyrrole homocoupling enzymology. Through a series of genetic experiments involving the discovery and heterologous expression of marinopyrrole biosynthesis genes, we report that two flavin-dependent halogenases catalyze the unprecedented homocoupling reaction.
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