A Biocatalytic Platform for the Synthesis of Enantiopure Propargylic Alcohols and Amines

Xianke Sang, Feifei Tong, Zhigang Zeng*, Minghu Wu, Bo Yuan, Zhoutong Sun, Xiang Sheng, Frank Hollmann, Wuyuan Zhang

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

2 Citations (Scopus)
12 Downloads (Pure)

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.

Original languageEnglish
Pages (from-to)4252-4257
JournalOrganic Letters
Volume24
Issue number23
DOIs
Publication statusPublished - 2022

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