Changing Face: A Key Residue for the Addition of Water by Sclareol Synthase,ACS Catalysis

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Changing Face: A Key Residue for the Addition of Water by Sclareol Synthase
ACS Catalysis ( IF 11.3 ) Pub Date : 2018-03-08 00:00:00 , DOI: 10.1021/acscatal.8b00121
Meirong Jia ₁ , Terrence E O'Brien ₂ , Yue Zhang ₂ , Justin B Siegel _{2,

3,

4} , Dean J Tantillo ₂ , Reuben J Peters ₁

Affiliation

Sclareol synthase from Salvia sclarea (SsSS) naturally acts on 8α-hydroxy-copalyl diphosphate (1), stereoselectively adding water to produce (13R)-sclareol (2a), and similarly yields hydroxylated products with many-fold other such bicyclic diterpene precursors. Here, a key residue for this addition of water was identified. Strikingly, substitution with glutamine switches stereochemical outcome with 1, leading to the selective production of (13S)-sclareol (2b). Moreover, changes to the stereospecificity of water addition with the structurally closely related substrate copalyl diphosphate (4) could be accomplished with alternative substitutions. Thus, this approach is expected to provide biosynthetic access to both epimers of 13-hydroxylated derivatives of many-fold labdane-related diterpenes.

中文翻译：

变脸：香紫苏醇合酶加水的关键残留

来自鼠尾草的香紫苏醇合酶 (SsSS) 天然作用于 8α-羟基-柯巴基二磷酸 ( 1 )，立体选择性地加水生成 (13 R )-香紫苏醇 ( 2a )，并类似地产生具有许多其他此类双环二萜前体的羟基化产物。在此，确定了添加水的关键残留物。引人注目的是，用谷氨酰胺取代会将立体化学结果转换为1 ，从而选择性产生 (13 S )-香紫苏醇 ( 2b )。此外，通过结构密切相关的底物二磷酸柯巴基 ( 4 ) 来改变水添加的立体特异性可以通过替代取代来实现。因此，这种方法有望提供多种 Labdane 相关二萜的 13-羟基化衍生物的两种差向异构体的生物合成途径。

更新日期：2018-03-08

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