20210211 Lin HC Epub

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

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

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

閱讀文章

Hewage RT, Huang RJ, Lai SJ, Lien YC, Weng SH, Li D, Chen YJ, Wu SH, Chein RJ, Lin HC

摘要

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 (1), 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 1 and imidazole to give 3S-imidazolyl conidiogenone B (6). Compound 6 was more potent than 1 against Staphylococcus aureus strains.