The Substrate Spectrum of the Inverting sec-Alkylsulfatase Pisa1
The Substrate Spectrum of the Inverting sec-Alkylsulfatase Pisa1
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DOI：
10.1002/adsc.201100864
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发表时间：
2012-06-01
影响因子：
5.4
通讯作者：
Faber, Kurt
中科院分区：
文献类型：
--
作者：
Schober, Markus;Knaus, Tanja;Faber, Kurt
底物光谱的转化烷基硫酸酯酶Pisa 1进行了研究，使用一系列的仲烷基硫酸酯轴承芳香族，烯烃和炔属部分。完美的对映体选择性得到不同大小的相邻的硫酸酯部分的基轴承基团的基板。不足的选择性可以通过使用二甲基亚砜（DMSO）作为共溶剂加倍。通过引入吸电子取代基，可以充分稳定水解不稳定的苄基硫酸酯。总的来说，Pisa 1似乎是一个非常有用的反相烷基硫酸酯酶的消旋-仲醇通过其相应的硫酸酯的酶促水解，这使具有反-Kazlauskas配置的纯手性产品去消旋化。
The substrate spectrum of the inverting alkylsulfatase Pisa1 was investigated using a range of sec-alkyl sulfate esters bearing aromatic, olefinic and acetylenic moieties. Perfect enantioselectivities were obtained for substrates bearing groups of different size adjacent to the sulfate ester moiety. Insufficient selectivities could be doubled by using dimethyl sulfoxide (DMSO) as co-solvent. Hydrolytically unstable benzylic sulfate esters could be sufficiently stabilised by introduction of electron-withdrawing substituents. Overall, Pisa1 appears to be a very useful inverting alkylsulfatase for the deracemisation of rac-sec-alcohols via enzymatic hydrolysis of their corresponding sulfate esters, which furnishes homochiral products possessing the anti-Kazlauskas configuration.