Improved enantioselective hydrolysis of racemic ethyl-2,2- dimethylcyclopropanecarboxylate catalyzed by modified novozyme 435

Biotechnology and Bioprocess Engineering

Volumn 17, Issue 5, 2012, Pages 952-958

  Liang, Fa Yong ^a   Huang, Jin ^a   He, Jun Yao ^a,b   Wang, Pu ^a  

^a ZHEJIANG UNIVERSITY OF TECHNOLOGY   (China)

^b ZHEJIANG PHARMACEUTICAL COLLEGE   (China)

Author keywords

Ethyl 2,2 dimethylcyclopropanecarboxylate; Glutaraldehyde; Modification; Novozyme 435; S (+) 2,2 dimethylcyclopropanecarboxylic acid

Indexed keywords

CHIRAL INTERMEDIATES; CILASTATIN; ENANTIOSELECTIVE HYDROLYSIS; ENZYMATIC PREPARATION; ETHYL-2,2-DIMETHYLCYCLOPROPANECARBOXYLATE; GLUTARALDEHYDES; HYDROLYTIC REACTIONS; INITIAL VALUES; MODIFICATION; MODIFIED ENZYMES; NOVOZYME 435; OPTICAL PURITY; OPTIMAL CONDITIONS; POTASSIUM PHOSPHATE; SPECIFIC ACTIVITY;

CARBOXYLATION; ENZYMATIC HYDROLYSIS; INDUSTRIAL APPLICATIONS; OPTIMIZATION;

ALDEHYDES;

2,2 DIMETHYLCYCLOPROPANECARBOXYLIC ACID; CYCLOPROPANECARBOXYLIC ACID DERIVATIVE; ETHYL 2,2 DIMETHYLCYCLOPROPANECARBOXYLATE; GLUTARALDEHYDE; LIPASE B; NOVOZYME 435; POTASSIUM DIHYDROGEN PHOSPHATE; UNCLASSIFIED DRUG;

ARTICLE; BIOCATALYST; CONCENTRATION RESPONSE; CONTROLLED STUDY; ENANTIOSELECTIVITY; ENZYME ACTIVITY; ENZYME MODIFICATION; HYDROLYSIS; PH; REACTION OPTIMIZATION; REACTION TIME; TEMPERATURE DEPENDENCE;

EID: 84871203504     PISSN: 12268372     EISSN: 19763816     Source Type: Journal    
DOI: 10.1007/s12257-012-0135-x     Document Type: Article

References (24)

1. Drusano, G. L. (1986) An overview of the pharmacology of imipenem/cilastatin. J. Antimicrob. Chemother. 18: 79-92.
2. Wang, P., J. N. Zhu, and J. Y. He (2010) Enantioselective synthesis of S-(+)-2,2-dimethylcyclopropanecarboxylic acid from ethyl-2,2- dimethylcyclopropanecarboxylate catalyzed by lipase Novozyme 435. Chin. J. Catal. 31: 651-655.
3. Wang, Q. W., F. K. Yang, H. Du, M. M. Hossain, D. Bennett, and D. S. Grubisha (1998) The synthesis of S-(+)-2,2-dimethylcyclopropane carboxylic acid: a precursor for cilastatin. Tetrahedron: Asymm. 9: 3971-3977.
4. Wang, M. X. and G. Q. Feng (2002) Enzymatic synthesis of optically active 2-methyl-And 2,2-dimethylcyclopropanecarboxylic acids and their derivatives. J. Mol. Catal. B: Enzym. 18: 267-272.
5. Panke, S., M. Held, and M. Wubbolts (2004) Trends and innovations in industrial biocatalysis for the production of fine chemicals. Curr. Opin. Biotechnol. 15: 272-279.
6. Straathof, A. J. J., S. Panke, and A. Schmid (2002) The production of fine chemicals by biotransformations. Curr. Opin. Biotechnol. 13: 548-556.
7. Yeom, S. J., H. J. Kim, and D. K. Oh (2007) Enantioselective production of 2,2-dimethylcyclopropane carboxylic acid from 2,2-dimethylcyclopropane carbonitrile using the nitrile hydratase and amidase of Rhodococcus erythropolis ATCC 25544. Enz. Microb. Technol. 41: 842-848.
8. Chen, B., J. Hu, E. M. Miller, W. C. Xie, M. M. Cai, and R. A. Gross (2008) Candida antarctica lipase B chemically immobilized on epoxy-Activated micro-And nanobeads: Catalysts for polyester synthesis. Biomacromol. 9: 463-471.
9. Reigada, J. B., C. M. Tcacenco, L. H. Andrade, M. J. Kato, A. L. M. Porto, and J. H. G. Lago (2007) Chemical constituents from Piper marginatum Jacq. (Piperaceae)-Antifungal activities and kinetic resolution of (RS)-marginatumol by Candida antarctica lipase (Novozym 435). Tetrahedron: Asymm. 18: 1054-1058.
10. He, L. P., J. Sun, Y. Xu, and Z. H. Sun (2008) A novel method to resolve (R,S)-3-n-butylphthalide catalyzed by Novozyme 435 in microaqueous medium. Proc. Biochem. 43: 1215-1219.
11. Cabrera, Z., G. Fernandez-Lorente, R. Fernandez-Lafuente, J. M. Palomo, and J. M. Guisan (2009) Novozym 435 displays very different selectivity compared to lipase from Candida antarctica B adsorbed on other hydrophobic supports. J. Mol. Catal. B: Enzym. 57: 171-176.
12. Royon, D., M. Daz, G. Ellenrieder, and S. Locatelli (2007) Enzymatic production of biodiesel from cotton seed oil using t-butanol as a solvent. Bioresour. Technol. 98: 648-653.
13. Hasan, F., A. A. Shah, and A. Hameed (2006) Industrial applications of microbial lipases. Enz. Microb. Technol. 39: 235-251.
14. Cabrera, Z., G. Fernandez-Lorente, R. Fernandez-Lafuente, J. M. Palomo, and J. M. Guisan (2009) Enhancement of Novozym-435 catalytic properties by physical or chemical modification. Proc. Biochem. 44: 226-231.
15. Shu, C. L., J. Cai, L. Huang, X. C. Zhu, and Z. N. Xu (2011) Biocatalytic production of ethyl butyrate from butyric acid with immobilized Candida rugosa lipase on cotton cloth. J. Mol. Catal. B: Enzym. 72: 139-144.
16. Talukder, M. M. R., J. C. Wu, T. B. Van Nguyen, N. M. Fen, and Y. L. S. Melissa (2009) Novozym 435 for production of biodiesel from unrefined palm oil: Comparison of methanolysis methods. J. Mol. Catal. B: Enzym. 60: 106-112.
17. Zhao, L. L., J. Pan, and J. H. Xu (2010) Efficient production of diltiazem chiral intermediate using immobilized lipase from Serratia marcescens. Biotechnol. Bioproc. Eng. 15: 199-207.
18. Viernstein, H., P. Weiss-Greiler, and P. Wolschann (2003) Solubility enhancement of low soluble biologically active compoundstemperature and cosolvent dependent inclusion complexation. Int. J. Pharm. 256: 85-94.
19. Weber, H. K., J. Zuegg, K. Faber, and J. Pleiss (1997) Molecular reasons for lipase-sensitivity against acetaldehyde. J. Mol. Catal. B: Enzym. 3: 131-138.
20. Liu, X. Q., Y. P. Guan, R. Shen, and H. Z. Liu (2005) Immobilization of lipase onto micron-size magnetic beads. J. Chromatogr. B 822: 91-97.
21. Huang, X. J., D. Ge, and Z. K. Xu (2007) Preparation and characterization of stable chitosan nanofibrous membrane for lipase immobilization. Eur. Polym. J. 43: 3710-3718.
22. Wang, P., J. B. Cai, Q. Ouyang, J. Y. He, and H. Z. Su (2011) Asymmetric biocatalytic reduction of 3,5-bis(trifluoromethyl) acetophenone to (1R)-[3,5-bis(trifluoromethyl)phenyl] ethanol using whole cells of newly isolated Leifsonia xyli HS0904. Appl. Microbiol. Biotechnol. 90: 1897-1904.
23. Dong, H. P., Y. J. Wang, and Y. G. Zheng (2010) Enantioselective hydrolysis of diethyl 3-hydroxyglutarate to ethyl (S)-3-hydroxyglutarate by immobilized Candida antarctica lipase B. J. Mol. Catal. B: Enzym. 66: 90-94.
24. Chen, Z. G., R. X. Tan, and M. Huang (2010) Efficient regioselective acylation of andrographolide catalyzed by immobilized Burkholderia cepacia lipase. Proc. Biochem. 45: 415-418.