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Environment-friendly and efficient synthesis of 2-aminobenzo-xazoles and 2-aminobenzothiazoles catalyzed by Vitreoscilla hemoglobin incorporating a cobalt porphyrin cofactor

Authors :
Nan Zhao
Lei Wang
Fengxi Li
Ciduo Wang
Yaning Xu
Zhengqiang Li
Chunyu Wang
Jiali Su
Source :
Green Chemistry. 23:8047-8052
Publication Year :
2021
Publisher :
Royal Society of Chemistry (RSC), 2021.

Abstract

In this study, an environment-friendly and efficient artificial Vitreoscilla hemoglobin (VHb) for the synthesis of 2-aminobenzoxazoles and 2-aminobenzothiazoles has been reported. We demonstrate an expression-based porphyrin substitution strategy to produce VHb containing cobalt porphyrin instead of native hemin, which can catalyze the oxidative cyclization of corresponding 2-aminobenzoxazoles and 2-aminobenthiazoles with up to 97% yield and 4850 catalytic turnovers in water under aerobic conditions. Hence, we provide a green and mild method for the synthesis of 2-aminobenzoxazoles and 2-aminobenzothiazoles. In addition, we indicate the value of porphyrin ligand substitution as a strategy to tune and enhance the catalytic properties of hemoproteins in non-natural reactions.

Details

ISSN :
14639270 and 14639262
Volume :
23
Database :
OpenAIRE
Journal :
Green Chemistry
Accession number :
edsair.doi...........133c824bff128114adaeb2530cf479b3