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一种酶介导的氮杂迈克尔加成反应参与了康定生酮 B 的咪唑杂合产物的生物合成。

An Enzyme-Mediated Aza-Michael Addition Is Involved in the Biosynthesis of an Imidazoyl Hybrid Product of Conidiogenone B.

机构信息

Institute of Biological Chemistry, Academia  Sinica, Taipei 115, Taiwan R.O.C.

Chemical Biology and Molecular Biophysics Program, Taiwan International Graduate Program, Academia Sinica, Taipei 115, Taiwan R.O.C.

出版信息

Org Lett. 2021 Mar 5;23(5):1904-1909. doi: 10.1021/acs.orglett.1c00330. Epub 2021 Feb 11.

DOI:10.1021/acs.orglett.1c00330
PMID:33570417
Abstract

Meleagrin B is a terpene-alkaloid hybrid natural product that contains both the conidiogenone and meleagrin scaffold. Their derivatives show diverse biological activities. We characterized the biosynthesis of (-)-conidiogenone B (), which involves a diterpene synthase and a P450 monooxygenase. In addition, an α,β-hydrolase (Con-ABH) was shown to catalyze an aza-Michael addition between and imidazole to give -imidazolyl conidiogenone B (). Compound was more potent than against strains.

摘要

美拉红碱 B 是一种萜类生物碱杂合天然产物,同时含有康皮定酮和美拉红碱骨架。它们的衍生物表现出多种生物活性。我们对 (-)-康皮定酮 B () 的生物合成进行了表征,其中涉及二萜合酶和 P450 单加氧酶。此外,还表明 α,β-水解酶 (Con-ABH) 可以催化 和咪唑之间的aza-Michael 加成反应,生成 -咪唑基康皮定酮 B ()。化合物 对 株的活性强于 。

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