Jump to main content
Jump to site search
Access to RSC content Close the message box

Continue to access RSC content when you are not at your institution. Follow our step-by-step guide.


Issue 7, 2020
Previous Article Next Article

A new monooxygenase from Herbaspirillum huttiense catalyzed highly enantioselective epoxidation of allylbenzenes and allylic alcohols

Author affiliations

Abstract

Asymmetric epoxidation is a green route to enantiopure epoxides, but often suffers from low enantioselectivity toward unconjugated terminal alkenes. Mining of the NCBI non-redundant protein sequences with a reconstructed ancestral sequence based on six styrene monooxygenases identified a monooxygenase (HhMo) from Herbaspirillum huttiense with 29.6–32.3% sequence identity with styrene monooxygenases, which was previously annotated as an alanine phosphoribitol ligase. HhMo catalyzed the epoxidation of allylbenzenes with moderate to excellent enantioselectivity yielding the corresponding epoxides in up to 99% ee. The HhMo-catalyzed epoxidation could also achieve the kinetic resolution of racemic secondary allylic alcohols, yielding the corresponding epoxides with up to 50% yields, as well as excellent enantio- and diastereoselectivity (up to >99% ee and >99% de) within 20–60 min, making a greener strategy for the production of valuable enantiopure glycidol derivatives in the fine chemical and pharmaceutical industries.

Graphical abstract: A new monooxygenase from Herbaspirillum huttiense catalyzed highly enantioselective epoxidation of allylbenzenes and allylic alcohols

Back to tab navigation

Supplementary files

Article information


Submitted
15 Jan 2020
Accepted
13 Feb 2020
First published
14 Feb 2020

Catal. Sci. Technol., 2020,10, 2145-2151
Article type
Paper

A new monooxygenase from Herbaspirillum huttiense catalyzed highly enantioselective epoxidation of allylbenzenes and allylic alcohols

H. Lin, Y. Tang, S. Dong, R. Lang and H. Chen, Catal. Sci. Technol., 2020, 10, 2145
DOI: 10.1039/D0CY00081G

Social activity

Search articles by author

Spotlight

Advertisements