In:
Angewandte Chemie, Wiley, Vol. 135, No. 16 ( 2023-04-11)
Abstract:
Herein, we disclose the highly enantioselective oxidative cross‐coupling of 3‐hydroxyindole esters with various nucleophilic partners as catalyzed by copper efflux oxidase. The biocatalytic transformation delivers functionalized 2,2‐disubstituted indolin‐3‐ones with excellent optical purity (90–99 % ee ), which exhibited anticancer activity against MCF‐7 cell lines, as shown by preliminary biological evaluation. Mechanistic studies and molecular docking results suggest the formation of a phenoxyl radical and enantiocontrol facilitated by a suited enzyme chiral pocket. This study is significant with regard to expanding the catalytic repertoire of natural multicopper oxidases as well as enlarging the synthetic toolbox for sustainable asymmetric oxidative coupling.
Type of Medium:
Online Resource
ISSN:
0044-8249
,
1521-3757
DOI:
10.1002/ange.v135.16
DOI:
10.1002/ange.202219034
Language:
English
Publisher:
Wiley
Publication Date:
2023
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505868-5
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506609-8
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514305-6
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505872-7
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1479266-7
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505867-3
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506259-7
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