Exploiting Designed Oxidase-Peroxygenase Mutual Benefit System for Asymmetric Cascade Reactions.

Da Yu,Manfred T Reetz,Jian-Bo Wang

doi:10.1021/jacs.9b01939

Abstract

A unique P450 monooxygenase–peroxygenase mutual benefit system was designed as the core element in the construction of a biocatalytic cascade reaction sequence leading from 3-phenyl propionic acid to (R)-phenyl glycol. In this system, P450 monooxygenase (P450-BM3) and P450 peroxygenase (OleTJE) not only function as catalysts for the crucial initial reactions, they also ensure an internal in situ H2O2 recycle mechanism that avoids its accumulation and thus prevents possible toxic effects. By directed evolution of P450-BM3 as the catalyst in the enantioselective epoxidation of the styrene-intermediate, formed from 3-phenyl propionic acid, and the epoxide hydrolase ANEH for final hydrolytic ring opening, (R)-phenyl glycol and 9 derivatives thereof were synthesized from the respective carboxylic acids in one-pot processes with high enantioselectivity.

Highlights

H2O2 is decomposed into water and oxygen by catalase or it is utilized by peroxidases or peroxygenases as an oxidant to generate new oxidative products.[15,16] based on the activities of oxidases and peroxidases/peroxygenases, cascade reactions with high economic efficiency can be created
A unique P450 monooxygenase−peroxygenase mutual benefit system was designed as the core element in the construction of a biocatalytic cascade reaction sequence leading from 3-phenyl propionic acid to (R)-phenyl glycol
By directed evolution of P450-BM3 as the catalyst in the enantioselective epoxidation of the styreneintermediate, formed from 3-phenyl propionic acid, and the epoxide hydrolase ANEH for final hydrolytic ring opening, (R)-phenyl glycol and 9 derivatives thereof were synthesized from the respective carboxylic acids in onepot processes with high enantioselectivity

Summary

Introduction

H2O2 is decomposed into water and oxygen by catalase or it is utilized by peroxidases or peroxygenases as an oxidant to generate new oxidative products.[15,16] based on the activities of oxidases and peroxidases/peroxygenases, cascade reactions with high economic efficiency can be created. ABSTRACT: A unique P450 monooxygenase−peroxygenase mutual benefit system was designed as the core element in the construction of a biocatalytic cascade reaction sequence leading from 3-phenyl propionic acid to (R)-phenyl glycol.

Results

Conclusion