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18-羟基多拉贝拉-3,7-二烯合酶——一种来自于……的二萜合酶

18-Hydroxydolabella-3,7-diene synthase - a diterpene synthase from .

作者信息

Dickschat Jeroen S, Rinkel Jan, Rabe Patrick, Beyraghdar Kashkooli Arman, Bouwmeester Harro J

机构信息

Kekulé-Institute of Organic Chemistry and Biochemistry, University of Bonn, Gerhard-Domagk-Straße 1, 53121 Bonn, Germany.

Laboratory of Plant Physiology, Wageningen University, Droevendaalsesteeg 1, 6708 PB Wageningen, The Netherlands.

出版信息

Beilstein J Org Chem. 2017 Aug 23;13:1770-1780. doi: 10.3762/bjoc.13.171. eCollection 2017.

Abstract

The product obtained in vitro from a diterpene synthase encoded in the genome of the bacterium , an enzyme previously reported to have germacrene A synthase activity during heterologous expression in , was identified by extensive NMR-spectroscopic methods as 18-hydroxydolabella-3,7-diene. The absolute configuration of this diterpene alcohol and the stereochemical course of the terpene synthase reaction were addressed by isotopic labelling experiments. Heterologous expression of the diterpene synthase in resulted in the production of 18-hydroxydolabella-3,7-diene also in planta, while the results from the heterologous expression in were shown to be reproducible, revealing that the expression of one and the same terpene synthase in different heterologous hosts may yield different terpene products.

摘要

从该细菌基因组中编码的二萜合酶体外获得的产物,这种酶先前在[具体宿主]中进行异源表达时被报道具有吉马烯A合酶活性,通过广泛的核磁共振光谱方法鉴定为18 - 羟基多拉贝拉 - 3,7 - 二烯。通过同位素标记实验确定了这种二萜醇的绝对构型以及萜烯合酶反应的立体化学过程。该二萜合酶在[具体宿主]中的异源表达也导致了植物中产生18 - 羟基多拉贝拉 - 3,7 - 二烯,同时在[另一具体宿主]中的异源表达结果被证明是可重复的,这表明在不同的异源宿主中表达同一个萜烯合酶可能产生不同的萜烯产物。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d334/5588592/6af985d3370b/Beilstein_J_Org_Chem-13-1770-g008.jpg

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