Issue 20, 2021

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

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.

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

Supplementary files

Article information

Article type
Paper
Submitted
16 juil. 2021
Accepted
01 sept. 2021
First published
06 sept. 2021

Green Chem., 2021,23, 8047-8052

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

Y. Xu, F. Li, N. Zhao, J. Su, C. Wang, C. Wang, Z. Li and L. Wang, Green Chem., 2021, 23, 8047 DOI: 10.1039/D1GC02533C

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements