| Autor: |
Hui Lin, Yinyin Meng, Na Li, Yanhong Tang, Shuang Dong, Zhongliu Wu, Cuilian Xu, Romas Kazlauskas, Hongge Chen |
| Rok vydání: |
2022 |
| Předmět: |
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| Zdroj: |
Angewandte Chemie (International ed. in English). 61(32) |
| ISSN: |
1521-3773 |
| Popis: |
The addition of water to alkenes is an important method for the synthesis of alcohols, but the regioselectivity of acid-catalyzed hydration of terminal alkenes yields secondary alcohols according to Markovnikov's rule, making it difficult to obtain primary alcohols. Here we report a styrene monooxygenase that catalyzes the anti-Markovnikov hydration of the terminal aryl alkenes under anaerobic conditions. This hydration provides primary alcohols in good yields (up to 100 %), excellent anti-Markovnikov regioselectivity (99 : 1), and good enantiomeric purity (60-83 % ee). Residues Asn46, Asp100, and Asn309 are essential for catalysis suggesting an acid-base mechanism with a carbanion-like intermediate that could account for the anti-Markovnikov regioselectivity. Our work reveals a new enzymatic tool with unusual regioselectivity based on the promiscuous catalytic activity of a monooxygenase. |
| Databáze: |
OpenAIRE |
| Externí odkaz: |
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