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박성훈

Park, Sunghoon
Biochemical Engineering Lab.
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Cloning and Characterization of a Novel Esterase from Rhodococcus sp. for Highly Enantioselective Synthesis of a Chiral Cilastatin Precursor

Author(s)
Zhang, YanPan, JiangLuan, Zheng-JiaoXu, Guo-ChaoPark, SunghoonXu, Jian-He
Issued Date
2014-12
DOI
10.1128/AEM.01597-14
URI
https://scholarworks.unist.ac.kr/handle/201301/25310
Fulltext
http://aem.asm.org/content/80/23/7348
Citation
APPLIED AND ENVIRONMENTAL MICROBIOLOGY, v.80, no.23, pp.7348 - 7355
Abstract
A novel nonheme chloroperoxidase (RhEst1), with promiscuous esterase activity for enantioselective hydrolysis of ethyl (S)-2,2-dimethylcyclopropanecarboxylate, was identified from a shotgun library of Rhodococcus sp. strain ECU1013. RhEst1 was overexpressed in Escherichia coli BL21(DE3), purified to homogeneity, and functionally characterized. Fingerprinting analysis revealed that RhEst1 prefers para-nitrophenyl (pNP) esters of short-chain acyl groups. pNP esters with a cyclic acyl moiety, especially that with a cyclobutanyl group, were also substrates for RhEst1. The K-m values for methyl 2,2-dimethylcyclopropanecarboxylate (DmCpCm) and ethyl 2,2-dimethylcyclopropane carboxylate (DmCpCe) were 0.25 and 0.43 mM, respectively. RhEst1 could serve as an efficient hydrolase for the bioproduction of optically pure (S)-2,2-dimethyl cyclopropane carboxylic acid (DmCpCa), which is an important chiral building block for cilastatin. As much as 0.5 M DmCpCe was enantioselectively hydrolyzed into (S)-DmCpCa, with a molar yield of 47.8% and an enantiomeric excess (ee) of 97.5%, indicating an extremely high enantioselectivity (E = 240) of this novel and unique biocatalyst for green manufacturing of highly valuable chiral chemicals.
Publisher
AMER SOC MICROBIOLOGY
ISSN
0099-2240

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