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Issue 18, 2018, Issue in Progress
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Efficient biocatalytic stereoselective reduction of methyl acetoacetate catalyzed by whole cells of engineered E. coli

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Abstract

Asymmetric synthesis of chiral β-hydroxy esters, the key building blocks for many functional materials, is currently of great interest. In this study, the biocatalytic anti-Prelog reduction of methyl acetoacetate (MAA) to methyl-(R)-3-hydroxybutyrate ((R)-HBME) was successfully carried out with high enantioselectivity using the whole cell of engineered E. coli, which harbored an AcCR (carbonyl reductase) gene from Acetobacter sp. CCTCC M209061 and a GDH (glucose dehydrogenase) gene from Bacillus subtilis 168 for the in situ regeneration of the coenzyme. Compared with the corresponding wild strain, the engineered E. coli cells were proved to be more effective for the bio-reduction of MAA, and afforded much higher productivity. Under the optimized conditions, the product e.e. was >99.9% and the maximum yield was 85.3% after a reaction time of 10 h, which were much higher than those reported previously. In addition, the production of (R)-HBME increased significantly by using a fed-batch strategy of tuning pH, with a space-time yield of approximately 265 g L−1 d−1, thus the issue in previous research of relatively low substrate concentrations appears to be solved. Besides, the established bio-catalytic system was proved to be feasible up to a 150 mL scale with a large-scale relatively high substrate concentration and selectivity. For further industrial application, these results open a way to use of whole cells of engineered E. coli for challenging higher substrate concentrations of β-ketone esters enantioselective reduction reactions.

Graphical abstract: Efficient biocatalytic stereoselective reduction of methyl acetoacetate catalyzed by whole cells of engineered E. coli

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Article information


Submitted
29 Jan 2018
Accepted
27 Feb 2018
First published
09 Mar 2018

This article is Open Access

RSC Adv., 2018,8, 9970-9978
Article type
Paper

Efficient biocatalytic stereoselective reduction of methyl acetoacetate catalyzed by whole cells of engineered E. coli

Y. H. Cui, P. Wei, F. Peng, M. H. Zong and W. Y. Lou, RSC Adv., 2018, 8, 9970
DOI: 10.1039/C8RA00883C

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