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Synthesis 2024; 56(04): 567-572
DOI: 10.1055/a-2076-9792
DOI: 10.1055/a-2076-9792
special topic
Synthetic Development of Key Intermediates and Active Pharmaceutical Ingredients (APIs)
Biocatalytic Synthesis of Chiral Benzylic Alcohols via Enantioselective Hydroxylation by a Self-Sufficient Cytochrome P450 from Deinococcus gobiensis
We are grateful for financial support from the National Natural Science Foundation of China (Nos. 21961048 and 32271537), the Guizhou Education Department Youth Science and Technology Talents Growth Project (QKHKY-2017-195), and the Science and Technology Department of Zunyi (ZSKH-2018-3, ZSKRPT-2020-5, and ZSKRPT-2021-5).
Abstract
Enzymatic asymmetric benzylic hydroxylation represents a green synthesis of valuable chiral benzylic alcohols. The stereoselective C–H direct hydroxylation profile possessed by cytochrome P450 monooxygenases (P450s) makes it more attractive. Here, we successfully expressed a self-sufficient cytochrome P450 monooxygenase from Deinococcus gobiensis in Escherichia coli BL21(DE3) host. The recombinant E. coli (P450DG) strain performed well in terms of functionality and has stereoselective benzylic hydroxylation ability for propylbenzene substrates. Asymmetric benzylic hydroxylation of various aromatic compounds was further investigated using the recombinant E. coli (P450DG) strain based on the optimal conditions, producing the corresponding enantioenriched pharmaceutically relevant benzylic alcohols in moderate yields with good to excellent enantioselectivity.
Key words
biocatalysis - cytochrome P450 - enantioselective hydroxylation - whole-cell bioconversion - chiral benzylic alcoholsSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-2076-9792.
- Supporting Information
Publication History
Received: 24 February 2023
Accepted after revision: 19 April 2023
Accepted Manuscript online:
19 April 2023
Article published online:
23 May 2023
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