Biocatalytic Preparation of Chiral Sulfoxides through Asymmetric Reductive Resolution by Methionine Sulfoxide Reductase A,ChemCatChem

当前位置： X-MOL 学术 › ChemCatChem › 论文详情

Our official English website, www.x-mol.net, welcomes your feedback! (Note: you will need to create a separate account there.)

Biocatalytic Preparation of Chiral Sulfoxides through Asymmetric Reductive Resolution by Methionine Sulfoxide Reductase A
ChemCatChem ( IF 3.8 ) Pub Date : 2018-05-28 , DOI: 10.1002/cctc.201800279
Liaotian Peng ₁ , Yuanmei Wen ₁ , Yu Chen ₂ , Zhimei Yuan ₁ , Yang Zhou ₁ , Xiaoling Cheng ₁ , Yongzheng Chen ₂ , Jiawei Yang ₁

Affiliation

Here we report an environmentally friendly method for the preparation of chiral sulfoxides under high substrate concentration using recombinant methionine sulfoxide reductase A from Pseudomonas monteilii (pmMsrA) as a biocatalyst. Our results show that this enzyme can effectively accomplish the preparation of (R)‐sulfoxides with approximately 50 % yield and 94–99 % enantiomeric excess through asymmetric reductive resolution of racemic sulfoxide. With the establishment of the enzyme regeneration system, the initial substrate concentration could be increased 40–100 times compared to our original report. The (R)‐sulfoxides were obtained with high enantioselectivity under the substrate concentration up to 200 mm (approximately 32 g L⁻¹), representing a quite high substrate concentration in biocatalytic preparation of chiral sulfoxides. Moreover, this system showed fairly good activity and enantioselectivity towards a series of ortho‐ and para‐substituted phenyl methyl sulfoxides under high substrate concentration.

中文翻译：

蛋氨酸亚砜还原酶A的不对称还原拆分生物催化制备手性亚砜

在这里，我们报告了一种环境友好的方法，该方法使用高浓度底物浓度的手性亚砜，使用来自假单胞菌的重组蛋氨酸亚砜还原酶A （pm MsrA）作为生物催化剂来制备。我们的结果表明，通过消旋亚消旋亚砜的不对称还原，该酶可以有效地完成（R）-亚砜的制备，产率约为50％，对映体过量为94-99％。通过建立酶再生系统，与我们的原始报告相比，底物的初始浓度可以增加40-100倍。（R）-亚砜是在底物浓度高达200 m m时以高对映体选择性获得的（约32g L ^-1），在手性亚砜的生物催化制备中代表相当高的底物浓度。而且，在高底物浓度下，该体系对一系列邻位和对位取代的苯基甲基亚砜表现出相当好的活性和对映选择性。

更新日期：2018-05-28

点击分享查看原文

点击收藏

阅读更多本刊新发论文本刊介绍/投稿指南