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Molecular cloning and functional characterization of a two highly stereoselective borneol dehydrogenases from Salvia officinalis L
Phytochemistry ( IF 3.2 ) Pub Date : 2020-04-01 , DOI: 10.1016/j.phytochem.2019.112227 Ivana Drienovská 1 , Dajana Kolanović 1 , Andrea Chánique 2 , Volker Sieber 3 , Michael Hofer 4 , Robert Kourist 1
Phytochemistry ( IF 3.2 ) Pub Date : 2020-04-01 , DOI: 10.1016/j.phytochem.2019.112227 Ivana Drienovská 1 , Dajana Kolanović 1 , Andrea Chánique 2 , Volker Sieber 3 , Michael Hofer 4 , Robert Kourist 1
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Enzymes for selective terpene functionalization are of particular importance for industrial applications. Pure enantiomers of borneol and isoborneol are fragrant constituents of several essential oils and find frequent application in cosmetics and therapy. Racemic borneol can be easily obtained from racemic camphor, which in turn is readily available from industrial side-streams. Enantioselective biocatalysts for the selective conversion of borneol and isoborneol stereoisomers would be therefore highly desirable for their catalytic separation under mild reaction conditions. Although several borneol dehydrogenases from plants and bacteria have been reported, none show sufficient stereoselectivity. Despite Croteau et al. describing sage leaves to specifically oxidize one borneol enantiomer in the late 70s, no specific enzymes have been characterized. We expected that one or several alcohol dehydrogenases encoded in the recently elucidated genome of Salvia officinalis L. would, therefore, be stereoselective. This study thus reports the recombinant expression in E. coli and characterization of two enantiospecific enzymes from the Salvia officinalis L. genome, SoBDH1 and SoBDH2, and their comparison to other known ADHs. Both enzymes produce preferentially (+)-camphor from racemic borneol, but (-)-camphor from racemic isoborneol.
中文翻译：
两种来自丹参的高立体选择性冰片脱氢酶的分子克隆和功能表征
用于选择性萜烯功能化的酶对于工业应用特别重要。冰片和异冰片的纯对映异构体是几种精油的芳香成分，经常用于化妆品和治疗。外消旋冰片可以很容易地从外消旋樟脑中获得，而外消旋樟脑又很容易从工业侧流中获得。因此，用于选择性转化冰片和异冰片立体异构体的对映选择性生物催化剂对于它们在温和反应条件下的催化分离是非常需要的。尽管已经报道了来自植物和细菌的几种冰片脱氢酶，但没有一种显示出足够的立体选择性。尽管克罗托等人。描述鼠尾草叶在 70 年代后期特异性氧化一种冰片对映异构体，但尚未表征特定的酶。因此，我们预计最近阐明的鼠尾草基因组中编码的一种或几种醇脱氢酶将具有立体选择性。因此，本研究报告了大肠杆菌中的重组表达和来自鼠尾草基因组的两种对映特异性酶 SoBDH1 和 SoBDH2 的表征，以及它们与其他已知 ADH 的比较。两种酶优先从外消旋冰片产生(+)-樟脑，但从外消旋异冰片产生(-)-樟脑。
更新日期：2020-04-01
中文翻译：
两种来自丹参的高立体选择性冰片脱氢酶的分子克隆和功能表征
用于选择性萜烯功能化的酶对于工业应用特别重要。冰片和异冰片的纯对映异构体是几种精油的芳香成分，经常用于化妆品和治疗。外消旋冰片可以很容易地从外消旋樟脑中获得，而外消旋樟脑又很容易从工业侧流中获得。因此，用于选择性转化冰片和异冰片立体异构体的对映选择性生物催化剂对于它们在温和反应条件下的催化分离是非常需要的。尽管已经报道了来自植物和细菌的几种冰片脱氢酶，但没有一种显示出足够的立体选择性。尽管克罗托等人。描述鼠尾草叶在 70 年代后期特异性氧化一种冰片对映异构体，但尚未表征特定的酶。因此，我们预计最近阐明的鼠尾草基因组中编码的一种或几种醇脱氢酶将具有立体选择性。因此，本研究报告了大肠杆菌中的重组表达和来自鼠尾草基因组的两种对映特异性酶 SoBDH1 和 SoBDH2 的表征，以及它们与其他已知 ADH 的比较。两种酶优先从外消旋冰片产生(+)-樟脑，但从外消旋异冰片产生(-)-樟脑。
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