Peroxygenase-Catalyzed Enantioselective Sulfoxidations
Peroxygenase-Catalyzed Enantioselective Sulfoxidations
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DOI：
10.1002/ejoc.201701390
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发表时间：
2017-12-22
影响因子：
2.8
通讯作者：
Monti, Daniela
中科院分区：
文献类型：
--
作者：
Bassanini, Ivan;Ferrandi, Erica Elisa;Monti, Daniela
研究了茶树菇非特异性过氧化物酶(AaeUPO)在取代芳基烷基硫醚不对称亚硫化反应中的催化性能。在AaeUPO和H_2O_2存在下，从相应的硫化物中成功地合成了一个不同取代的芳基烷基亚砜的小分子文库。无论芳环和烷基链上的取代方式如何，所有亚砜都是以(R)-对映体的形式得到的，转化率高达99%，ee高达99%。本文还对手性亚硫醚的生物催化条目进行了概述，将AaeUPO的结果与烟青霉和三种不同的Baeyer-Villiger单加氧酶的氯代过氧化物酶的性能进行了比较。据我们所知，这是系统研究杂原子不对称氧化中AaeUPO合成势的第一个例子，即硫化物的亲立体生成硫。
The performances of the unspecific peroxigenase from Agrocybe aegerita (AaeUPO) in the asymmetric sulfoxidation of substituted aryl alkyl sulfides were here investigated. A small library of differently substituted aryl alkyl sulfoxides was successfully synthesized from the corresponding sulfides in the presence of AaeUPO and H2O2. All the sulfoxides were obtained as (R)-enantiomers, regardless the substitution pattern both on the aromatic ring and the alkyl chain, in up to > 99% conversion and > 99% ee. An overview about the biocatalytic entries to chiral sulfoxides is also presented here in form of a comparison between the results obtained with AaeUPO and performances of the chloroperoxidase from Caldariomyces fumago, and three different Baeyer-Villiger monooxygenases. To the best our knowledge, this is the first example of a systematic investigation of the AaeUPO synthetic potential in the asymmetric oxidation of hetero atoms, i.e., the pro-stereogenic sulfur of sulfides.