Preparation of ethyl 3R,5S-6-(benzyloxy)-3,5-dihydroxy-hexanoate by recombinant diketoreductase in a biphasic system

Bioresource Technology

Volumn 102, Issue 3, 2011, Pages 3649-3652

  Wu, Xuri ^a   Chen, Chen ^a   Liu, Nan ^a   Chen, Yijun ^a,b  

^a CHINA PHARMACEUTICAL UNIVERSITY   (China)

^b RUTGERS UNIVERSITY   (United States)

Author keywords

Biocatalysis; Biphasic system; Diketoreductase; Statin drugs

Indexed keywords

ACINETOBACTERS; BIOCATALYSIS; BIPHASIC REACTION; BIPHASIC SYSTEMS; CARBONYL REDUCTASE; CATALYTIC PROPERTIES; DIKETOREDUCTASE; HEXANOATE; OXIDOREDUCTASES; REACTION CONDITIONS; STATIN DRUGS; SUBSTRATE CONCENTRATIONS;

HEXANE;

ORGANIC SOLVENTS;

CARBONYL REDUCTASE; DIKETOREDUCTASE; ETHYL 6 (BENZYLOXY) 3,5 DIHYDROXY HEXANOATE; HEXANE; HEXANOIC ACID; ORGANIC SOLVENT; RECOMBINANT ENZYME; UNCLASSIFIED DRUG;

AROMATIC HYDROCARBON; BACTERIUM; CATALYST; DRUG; ENZYME ACTIVITY; OPTIMIZATION; ORGANIC COMPOUND; RECOMBINATION; SOLVENT;

ACINETOBACTER; AQUEOUS SOLUTION; ARTICLE; BACTERIAL STRAIN; BIOCATALYSIS; BIOCATALYST; CONTROLLED STUDY; CROSS COUPLING REACTION; ENZYME MECHANISM; NONHUMAN; PRIORITY JOURNAL; SCALE UP; STEREOCHEMISTRY; SYNTHESIS;

ACINETOBACTER; CAPROATES; OXIDOREDUCTASES; PHASE TRANSITION; RECOMBINANT PROTEINS;

ACINETOBACTER BAYLYI;

EID: 78650817253     PISSN: 09608524     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.biortech.2010.11.104     Document Type: Article

References (13)

1. Bommarius A.S., Schwarm M., Drauz K. Biocatalysis to amino acid-based chiral pharmaceuticals - examples and perspectives. J. Mol. Catal. B: Enzym. 1998, 5:1-11.
2. Guo Z.W., Chen Y.J., Goswami A., Hanson R.L., Patel R.N. Synthesis of ethyl and t-butyl (3R,5S)-dihydroxy-6-benzyloxy hexanoates via diastereo and enantioselective microbial reduction. Tetrahedron Asymmetr. 2006, 17:1589-1602.
3. Klibanov A.M. Improving enzymes by using them in organic solvents. Nature 2001, 409:241-246.
4. Klibanov A.M. Asymmetric enzymatic oxidoreductions in organic solvents. Curr. Opin. Biotechnol. 2003, 14:427-431.
5. Liu J.H., Yu B.Y., Chen Y.J. Determination of enantiomeric excess of ethyl 3,5-dihydroxy-6-benzyloxy hexanoate by chiral reverse phase high performance liquid chromatography. Chirality 2008, 20:51-53.
6. Müller M. Chemoenzymatic synthesis of building blocks for statin side chain. Angew. Chem. Int. Ed. 2005, 44:362-365.
7. Patel R.N. Synthesis of chiral pharmaceuticals intermediates by biocatalysis. Coord. Chem. Rev. 2008, 252:659-701.
8. Shuber A.P., Orr E.C., Recny M.A., Schendel P.F., May H.D., Schauer N.L., Ferry J.G. Cloning, expression and nucleotide sequence of the formate dehydrogenase genes from Methanobacterium formicicum. J. Biol. Chem. 1986, 261:12942-12947.
9. Torre O., Busto E., Gotor-Fernändez V., Gotor V. Enzymatic preparation of novel aminoalkylpyridines using lipases in organic solvents. Adv. Synth. Catal. 2007, 349:1481-1488.
10. Wu, X.R., Liu, N., He, Y.M., Chen, Y.J., 2008. A bacterial enzyme catalyzing double reduction of α, β, δ-diketo ester with unprecedented stereoselectivity. Nature Proceedings. <>. http://hdl.handle.net/10101/npre.2008.1697.1.
11. Wu X.R., Liu N., He Y.M., Chen Y.J. Cloning, expression and characterization of a novel diketoreductase from Aceinetobacter baylyi. Acta Biochim. Biophys. Sin. 2009, 41:163-170.
12. Wu X.R., Wang L.L., Wang S.Z., Chen Y.J. Stereoselective introduction of two chiral centers by a single diketoreductase: an efficient biocatalytic route for the synthesis of statin side chains. Amino Acids 2010, 39:305-308.
13. Zhu D.M., Malik H.T., Hua L. Asymmetric ketone reduction by a hyperthermophilic alcohol dehydrogenase. The substrate specificity, enantioselectivity and tolerance of organic solvents. Tetrahedron Asymmetr. 2006, 17:3010-3014.