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Asymmetric Epoxidation and Sulfoxidation Catalyzed by a New Styrene Monooxygenase from Bradyrhizobium.
Applied Biochemistry and Biotechnology ( IF 3.1 ) Pub Date : 2020-08-18 , DOI: 10.1007/s12010-020-03413-8
Can Cui 1, 2 , Hui Lin 3 , Wei Pu 1, 2 , Chao Guo 1 , Yan Liu 1 , Xiao-Qiong Pei 1 , Zhong-Liu Wu 1
Affiliation  

Asymmetric epoxidation catalyzed with styrene monooxygenase (SMO) is a powerful enzymatic process producing enantiopure styrene epoxide derivatives. To establish a more diversified reservoir of SMOs, a new SMO from Bradyrhizobium sp. ORS 375, named BrSMO, was mined from the database and characterized. BrSMO was constituted of an epoxygenase component of 415 amino acid residues and an NADH-dependent flavin reductase component of 175 residues. BrSMO catalyzed the epoxidation of styrene and 7 more styrene derivatives, yielding the corresponding (S)-epoxides with excellent enantiomeric excesses (95– > 99% ee), with the highest activity achieved for styrene. BrSMO also catalyzed the asymmetric sulfoxidation of 7 sulfides, producing the corresponding (R)-sulfoxides (20–90% ee) with good yields.



中文翻译:

新型根瘤菌的苯乙烯单加氧酶催化的不对称环氧化和磺氧化。

苯乙烯单加氧酶(SMO)催化的不对称环氧化是一种强大的酶促工艺,可生产对映纯的苯乙烯环氧化物衍生物。为了建立更多样化的SMO储存库,一种来自Bradyrhizobium sp。的新SMO 。从数据库中提取了一个名为Br SMO的ORS 375,并对其进行了表征。Br SMO由415个氨基酸残基的环氧合酶成分和175个残基的NADH依赖性黄素还原酶成分组成。Br SMO催化苯乙烯和其他7种苯乙烯衍生物的环氧化,得到相应的(S)-环氧化合物,其对映体过量极好(95-> 99%ee),对苯乙烯的活性最高。SMO还催化7种硫化物的不对称硫氧化,从而以高收率产生相应的(R)-亚砜(20-90%ee)。

更新日期:2020-08-18
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