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Preparation of ethyl 3R,5S-6-(benzyloxy)-3,5-dihydroxy-hexanoate by recombinant diketoreductase in a biphasic system.
Bioresour Technol. 2011 Feb; 102(3):3649-52.BT

Abstract

Diketoreductase from Acinetobacter baylyi ATCC 33305 is a unique carbonyl reductase, which can stereoselectively reduce ethyl-6-(benzyloxy)-3,5-dioxohexanoate to ethyl 3R,5S-6-(benzyloxy)-3,5-dihydroxy-hexanoate, an advanced intermediate for statin drugs. In the present study, we explored an aqueous-organic biphasic reaction system to make this biocatalyst more practical and valuable. Different from most oxidoreductases, diketoreductase displayed an excellent tolerance to certain organic solvents without any changes on the catalytic properties. After optimizing reaction conditions, an aqueous-hexane (1:1) biphasic system was established for the preparation of 3R,5S-dihydroxy product by diketoreductase. This system was further scaled up to 0.5 l at a substrate concentration of 105 g/l (378 mM), and the 3R,5S-hydroxy product was obtained with a yield of 83.5% and excellent stereoselectivity (de>99.5%, ee>99.5%).

Authors+Show Affiliations

Laboratory of Chemical Biology, School of Life Science and Technology, China Pharmaceutical University, Nanjing, Jiangsu Province, PR China.No affiliation info availableNo affiliation info availableNo affiliation info available

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

21163644

Citation

Wu, Xuri, et al. "Preparation of Ethyl 3R,5S-6-(benzyloxy)-3,5-dihydroxy-hexanoate By Recombinant Diketoreductase in a Biphasic System." Bioresource Technology, vol. 102, no. 3, 2011, pp. 3649-52.
Wu X, Chen C, Liu N, et al. Preparation of ethyl 3R,5S-6-(benzyloxy)-3,5-dihydroxy-hexanoate by recombinant diketoreductase in a biphasic system. Bioresour Technol. 2011;102(3):3649-52.
Wu, X., Chen, C., Liu, N., & Chen, Y. (2011). Preparation of ethyl 3R,5S-6-(benzyloxy)-3,5-dihydroxy-hexanoate by recombinant diketoreductase in a biphasic system. Bioresource Technology, 102(3), 3649-52. https://doi.org/10.1016/j.biortech.2010.11.104
Wu X, et al. Preparation of Ethyl 3R,5S-6-(benzyloxy)-3,5-dihydroxy-hexanoate By Recombinant Diketoreductase in a Biphasic System. Bioresour Technol. 2011;102(3):3649-52. PubMed PMID: 21163644.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Preparation of ethyl 3R,5S-6-(benzyloxy)-3,5-dihydroxy-hexanoate by recombinant diketoreductase in a biphasic system. AU - Wu,Xuri, AU - Chen,Chen, AU - Liu,Nan, AU - Chen,Yijun, Y1 - 2010/11/30/ PY - 2010/08/17/received PY - 2010/11/22/revised PY - 2010/11/24/accepted PY - 2010/12/18/entrez PY - 2010/12/18/pubmed PY - 2011/4/22/medline SP - 3649 EP - 52 JF - Bioresource technology JO - Bioresour. Technol. VL - 102 IS - 3 N2 - Diketoreductase from Acinetobacter baylyi ATCC 33305 is a unique carbonyl reductase, which can stereoselectively reduce ethyl-6-(benzyloxy)-3,5-dioxohexanoate to ethyl 3R,5S-6-(benzyloxy)-3,5-dihydroxy-hexanoate, an advanced intermediate for statin drugs. In the present study, we explored an aqueous-organic biphasic reaction system to make this biocatalyst more practical and valuable. Different from most oxidoreductases, diketoreductase displayed an excellent tolerance to certain organic solvents without any changes on the catalytic properties. After optimizing reaction conditions, an aqueous-hexane (1:1) biphasic system was established for the preparation of 3R,5S-dihydroxy product by diketoreductase. This system was further scaled up to 0.5 l at a substrate concentration of 105 g/l (378 mM), and the 3R,5S-hydroxy product was obtained with a yield of 83.5% and excellent stereoselectivity (de>99.5%, ee>99.5%). SN - 1873-2976 UR - https://www.unboundmedicine.com/medline/citation/21163644/Preparation_of_ethyl_3R5S_6__benzyloxy__35_dihydroxy_hexanoate_by_recombinant_diketoreductase_in_a_biphasic_system_ L2 - https://linkinghub.elsevier.com/retrieve/pii/S0960-8524(10)01907-3 DB - PRIME DP - Unbound Medicine ER -