Piezobiocatalysis: Ultrasound-Driven Enzymatic Oxyfunctionalization of C-H Bonds

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Peroxygenases have long inspired the selective oxyfunctionalization of various aliphatic and aromatic compounds, because of their broad substrate spectrum and simplicity of catalytic mechanism. This study provides a proof-of-concept of piezobiocatalysis by demonstrating peroxygenase-catalyzed oxyfunctionalization reactions fueled by piezocatalytically generated H2O2. Bismuth oxychloride (BiOCl) generated H2O2 in situ via an oxygen reduction reaction under ultrasonic wave conditions. Through the simple combination of water, ultrasound, recombinant, evolved unspecific peroxygenase from Agrocybe aegerita (rAaeUPO), and BiOCl, the piezobiocatalytic platform accelerated selective hydroxylation of ethylbenzene to enantiopure (R)-1-phenylethanol [total turnover number of rAaeUPO (TTNrAaeUPO), 2002; turnover frequency, 77.7 min(-1); >99% enantiomeric excess (ee)]. The BiOCl-rAaeUPO couple also catalyzed other representative substrates (e.g., propylbenzene, 1-chloro-4-ethylbenzene, cyclohexane, and cis-beta-methylstyrene) with high turnover frequency and selectivity. We alleviated the oxidative stress of piezocatalytically generated OH center dot on rAaeUPO by spatial separation of rAaeUPO and BiOCl, which resulted in greatly enhanced TTNrAaeUPO of >3900 and the notable prolongation of reaction time. Overall, the BiOCl-rAaeUPO couple serves as a mechanical-to-chemical energy conversion platform for driving peroxygenase-catalyzed reactions under ultrasonic conditions.
Publisher
AMER CHEMICAL SOC
Issue Date
2020-05
Language
English
Article Type
Article
Citation

ACS CATALYSIS, v.10, no.9, pp.5236 - 5242

ISSN
2155-5435
DOI
10.1021/acscatal.0c00188
URI
http://hdl.handle.net/10203/274315
Appears in Collection
MS-Journal Papers(저널논문)
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