A Biocatalytic Platform for the Synthesis of Enantiopure Propargylic Alcohols and Amines
Xianke Sang (Chinese Academy of Sciences)
Feifei Tong (Chinese Academy of Sciences)
Zhigang Zeng (Hubei University of Science and Technology, Hubei)
Minghu Wu (Hubei University of Science and Technology, Hubei)
Bo Yuan (Chinese Academy of Sciences)
Zhoutong Sun (Chinese Academy of Sciences)
Xiang Sheng (Chinese Academy of Sciences)
Frank Hollmann (TU Delft - BT/Biocatalysis)
Wuyuan Zhang (TU Delft - BT/Biocatalysis, Chinese Academy of Sciences)
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Abstract
Propargylic alcohols and amines are versatile building blocks in organic synthesis. We demonstrate a straightforward enzymatic cascade to synthesize enantiomerically pure propargylic alcohols and amines from readily available racemic starting materials. In the first step, the peroxygenase from Agrocybe aegerita converted the racemic propargylic alcohols into the corresponding ketones, which then were converted into the enantiomerically pure alcohols using the (R)-selective alcohol dehydrogenase from Lactobacillus kefir or the (S)-selective alcohol dehydrogenase from Thermoanaerobacter brokii. Moreover, an enzymatic Mitsunobu-type conversion of the racemic alcohols into enantiomerically enriched propargylic amines using (R)-selective amine transaminase from Aspergillus terreus or (S)-selective amine transaminase from Chromobacterium violaceum was established. The one-pot two-step cascade reaction yielded a broad range of enantioenriched alcohol and amine products in 70-99% yield.
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