Efficient production of diltiazem chiral intermediate using immobilized lipase from serratia marcescens

Biotechnology and Bioprocess Engineering

Volumn 15, Issue 2, 2010, Pages 199-207

  Zhao, Li Li ^a   Pan, Jiang ^a   Xu, Jian He ^a  

^a EAST CHINA UNIVERSITY OF SCIENCE AND TECHNOLOGY   (China)

Author keywords

( ) MPGM; Chitosan; Enzyme immobilization; Isopropyl ether; Lipase; Serratia marcescence; Stirred tank reactor

Indexed keywords

(-)-MPGM; ISOPROPYL ETHERS; SERRATIA; SERRATIA MARCESCENCE; STIRRED TANK REACTORS;

ALDEHYDES; CHITIN; CHITOSAN; ENZYME ACTIVITY; ENZYMES; ESTERS; ETHERS; ORGANIC SOLVENTS; SYNTHESIS (CHEMICAL); SYSTEM STABILITY; TOLUENE;

ENZYME IMMOBILIZATION;

2 DIETHYLAMINOETHANOL; 3 (4' METHOXYPHENYL)GLYCIDIC ACID METHYL ESTER; CELLULOSE; CHITOSAN; DIISOPROPYL ETHER; DILTIAZEM; GLYCINE DERIVATIVE; INFUSORIAL EARTH; TRIACYLGLYCEROL LIPASE; UNCLASSIFIED DRUG;

ARTICLE; BIOREACTOR; CATALYSIS; CHIRALITY; DRUG MANUFACTURE; ENZYME IMMOBILIZATION; HYDROLYSIS; PH; SERRATIA MARCESCENS;

SERRATIA; SERRATIA MARCESCENS;

EID: 77953604136     PISSN: 12268372     EISSN: None     Source Type: Journal    
DOI: 10.1007/s12257-009-0173-1     Document Type: Article

References (34)

1. Nagao, T., M. Sato, H. Nakajima, and A. Kiyomoto (1972) Studies on a new 1, 5-benzothiazepine derivative (CRD-401). II. Vasodilator actions. Jpn. J. Pharmacol. 22: 1-10.
2. Abe, K., H. Inoue, and T. Nagao (1988) Diltiazem hydrochloride: synthetic and pharmacological studies and development. Yakugaku Zasshi 108: 716-732.
3. Lopez, J. L. and S. L. Matson (1997) A multiphase/extractive enzyme membrane reactor for production of diltiazem chiral intermediate. J. Membr. Sci. 125: 189-211.
4. Shibatani, T., K. Omori, H. Akatsuka, E. Kawai, and H. Matsumae (2000) Enzymatic resolution of diltiazem intermediate by Serratia marcescens lipase: molecular mechanism of lipase secretion and its industrial application. J. Mol. Catal. B: Enzymatic 10: 141-149.
5. Dodds, D. R. and J. L. Lopez (1993) Enzymatic hydrolysis of glycidate esters in the presence of bisulfite anion. US Patent 5,274,300.
6. Hulshof, L. A. and J. H. Roskan (1989) Phenylglycidate stereoisomers, conversion products thereof with e.g. 2-nitrothiophenol and preparation of diltiazem. WO Patent 343,714.
7. Matsumae, H., M. Furui, T. Shibatani, and T. Tosa (1994) Production of optically active 3-phenylglycidic acid ester by the Serratia marcescens lipase on a hollow fibre membrane reactor. J. Ferment. Bioeng. 78: 59-63.
8. Shibatani, T. and K. Nakamichi (1990) Method for preparing optically active 3-phenylglycidic acid esters. WO Patent 362,556.
9. Rosu, R., Y. Vozaki, Y. Iwasaki, and T. Yamane (1997) Repeated use of immobilized lipase for monoacylglycerol production by solid-phase glycerolysis of olive oil. J. Am. Oil Chem. Soc. 74: 445-450.
10. Bornscheuer, U. T. and T. Yamane (1994) Activity and stability of lipase in the solid-phase glycerolysis of triolein. Enzym. Microb. Technol. 16: 864-869.
11. Brady, C., L. Metcalfe, D. Slaboszewski, and D. Frank (1988) Lipase immobilized on a hydrophobic microporous supports for the hydrolysis of fats. J. Am. Oil Chem. Soc. 65: 917-921.
12. Gao, L., J. H. Xu, X. J. Li and Z. Z. Liu (2004) Optimization of Serratia marcescens lipase production for enantioselective hydrolysis of 3-phenylglycidic acid ester. J. Ind. Microbiol. Biotechnol. 31: 525-530.
13. Zhao, L. L., J. H. Xu, J. Zhao, J. Pan, and Z. L. Wang (2008) Biochemical properties and potential applications of an organic solvent tolerant lipase isolated from Serratia marcescens ECU1010. Process Biochem. 43: 626-633.
14. Long, Z. D., J. H. Xu, and J. Pan (2007) Immobilization of Serratia marcescens lipase and catalytic resolution of trans-3-(4′-methoxyphenyl) glycidic acid methyl ester. Chin. J. Catal. 28: 175-179.
15. Crotti, P., M. Terretti, F. Macchia, and A. Stoppioni (1986) Ring-opening reaction of cis- and trans-2,3-bis(4-methoxybenzyl) oxirane: competition between assistance by and migration of an aryl group. J. Org. Chem. 51: 2759-2766.
16. Long, Z. D., J. H. Xu, and J. Pan (2007) Significant improvement of Serratia marcescens lipase fermentation, by optimizing medium, induction, and oxygen supply. Appl. Biochem. Biotechnol. 142: 148-157.
17. Arruda, E. J. and C. C. Santana (2003) Phenylboronate-chitosan resins for adsorption of β-amylase from soybean extracts. Appl. Biochem. Biotechnol. 105: 829-842.
18. Kosaka, P. M., Y. Kawano, O. A. El Seoud, and D. F. S. Petri (2007) Catalytic activity of lipase immobilized onto ultrathin films of cellulose esters. Langmuir 23: 12167-12173. (Pubitemid 350197387)
19. Kosugi, Y., H. Tanaka, and N. Tomizuka (1990) Continuous hydrolysis of oil by immobilized lipase in a counter current reactor. Biotechnol. Bioeng. 36: 617-622.
20. Matsumae, H., M. Furui, and T. Shibatani (1993) Lipasecatalyzed asymmetric hydrolysis of 3-Phenylglycidic acid ester, the key intermediate in the synthesis of Diltiazem hydrochloride. J. Ferment. Bioeng. 75: 93-98.
21. Alloue, W. A., J. Destain, T. El Medjoub, H. Ghalfi, P. Kabran, and P. Thonart (2008) Comparison of Yarrowia lipolytica lipase immobilization yield of entrapment, adsorption, and covalent bond techniques. Appl. Biochem. Biotechnol. 150: 51-63.
22. Deng, H. T., Z. K. Xu, Z. M. Liu, J. Wu, and P. Ye (2004) Adsorption immobilization of Candida rugosa lipases on polypropylene hollow fiber microfiltration membranes modified by hydrophobic polypeptides. Enzym. Microb. Technol. 35: 437-443.
23. Knezevic, Z., N. Milosavic, D. Bezbradica, Z. Jakovljevic, and R. Prodanovic (2006) Immobilization of lipase from Candida rugosa on Eupergit® C supports by covalent attachment. Biochem. Eng. J. 30: 269-278.
24. Palomo, J. M., R. L. Segura, G. F. Lorente, R. F. Lafuente, and J. M. Guisan (2007) Glutaraldehyde modification of lipases adsorbed on aminated supports: a simple way to improve their behavior as enantioselective biocatalyst. Enzym. Microb. Technol. 40: 704-707.
25. Krajewska, B. (2004) Application of chitin- and chitosan-based materials for enzyme immobilizations: a review. Enzym. Microb. Technol. 35: 126-139.
26. Munjal, N. and S. K. Sawhney (2002) Stability and properties of mushroom tyrosinase entrapped in alginate, polyacrylamide and gelatin gels. Enzym. Microb. Technol. 30: 613-619.
27. Montero, S., A. Blanco, M. D. Virto, L. C. Landeta, I. Agud, and R. Solozabal (1993) Immobilization of Candida rugosa lipase and some properties of the immobilized enzyme. Enzym. Microb. Technol. 15: 239-247.
28. Hilterhaus, L., O. Thum, and A. Liese (2008) Reactor concept for lipase-catalyzed solvent-free conversion of highly viscous reactants forming two-phase systems. Org. Process Res. Dev. 12: 618-625.
29. Van Aken, B. P., L. Henry, N. Spiros, and N. Agathos (2000) Co-immobilization of manganese peroxidase from Phlebia radiata on porous silica beads. Biotechnol. Lett. 8: 641-646.
30. Seyhan, T. S. and O. Alptekin (2004) Immobilization and kinetics of catalase onto magnesium silicate. Process Biochem. 39: 2149-2155.
31. Lamas, E. M., R. M. Barros, V. M. Balcão, and F. X. Malcata (2001) Hydrolysis of whey proteins by proteases extracted from Cynara cardunculus and immobilized onto highly activated supports. Enzym. Microb. Technol. 28: 642-652.
32. Mohammad, T. B. and M. T. Bustard (2008) Fed batch bioconversion of 2-propanol by a solvent tolerant strain of Alcaligenes faecalis entrapped in Ca-alginate gel. J. Ind. Microbiol. Biotechnol. 35: 677-684.
33. Biró, E., A. Sz. Németh, C. Sisak, T. Feczkó, and J. Gyenis (2008) Preparation of chitosan particles suitable for enzyme immobilization. J. Biochem. Biophys. Methods 70: 1240-1246.
34. Kasche, V. (1983) Correlation of experimental and theoretical data for artificial and natural systems with immobilized biocatalysts. Enzym. Microb. Technol. 5: 2-13.