Late-Stage Terpene Cyclization by an Integral Membrane Cyclase in the Biosynthesis of Isoprenoid Epoxycyclohexenone Natural Products,Organic Letters

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Late-Stage Terpene Cyclization by an Integral Membrane Cyclase in the Biosynthesis of Isoprenoid Epoxycyclohexenone Natural Products
Organic Letters ( IF 4.9 ) Pub Date : 2017-09-19 00:00:00 , DOI: 10.1021/acs.orglett.7b02653
Man-Cheng Tang , Xiaoqing Cui ₁ , Xueqian He ₁ , Zhuang Ding ₁ , Tianjiao Zhu ₁ , Yi Tang , Dehai Li _{1,

2}

Affiliation

Macrophorins are representative examples of isoprenoid epoxycyclohexenones containing cyclized drimane moieties. We located and characterized the biosynthetic gene cluster of macrophorin from Penicillium terrestris. MacJ encoded by this cluster was characterized to be the first example of a membrane-bound type-II terpene cyclase catalyzing the cyclization of meroterpenoids via direct protonation of the terminal olefinic bond in acyclic yanuthones. The late-stage functionalization and substrate promiscuity of MacJ make it a potential biocatalyst for the synthesis of macrophorin analogues.

中文翻译：

晚期膜环化的整体膜环化酶在类异戊二烯环氧环己烯酮天然产物的生物合成中的作用

大蛋白是含有环化的drimane部分的类异戊二烯环氧环己酮的代表性实例。我们定位并表征了青霉青霉的大隐蛋白的生物合成基因簇。由该簇编码的MacJ被表征为膜结合的II型萜烯环化酶的第一个实例，该酶通过无环yan酮中末端烯烃键的直接质子化催化类萜的环化。MacJ的后期功能化和底物混杂使其成为合成大隐蛋白类似物的潜在生物催化剂。

更新日期：2017-09-19

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