Biosynthesis of Shearinine: Diversification of a Tandem Prenyl Moiety of Fungal Indole Diterpenes
Biosynthesis of Shearinine: Diversification of a Tandem Prenyl Moiety of Fungal Indole Diterpenes
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DOI：
10.1021/acs.orglett.6b02482
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发表时间：
2016-10-07
期刊：
影响因子：
5.2
通讯作者：
Oikawa, Hideaki
中科院分区：
文献类型：
--
作者：
Liu, Chengwei;Minami, Atsushi;Oikawa, Hideaki
使用米曲霉的高效异源表达系统阐明了涉及四个酶促反应（JanQDOJ）的吲哚二萜剪切力的后期生物合成途径。使用底物类似物和含有 (H2O)-O-18 的缓冲液研究了关键的氧化环化，通过黄素蛋白氧化酶形成特征性 A/B 双环 sherinine 核心。这些实验数据证明 JanO 通过羟基化产物催化两步氧化，并且 JanO 反应涉及氢化物转移机制。
The late-stage biosynthetic pathway of the indole diterpene shearinine involving four enzymatic reactions (JanQDOJ) was elucidated by an efficient heterologous expression system using Aspergillus oryzae. Key oxidative cyclization, forming a characteristic A/B bicyclic shearinine core by flavoprotein oxidase, was studied using a substrate analogue and a buffer containing (H2O)-O-18. These experimental data provided evidence that JanO catalyzes two-step oxidation via a hydroxylated product and that the JanO reaction involves the hydride-transfer mechanism.