A chemically modified lipase preparation for catalyzing the transesterification reaction in even highly polar organic solvents

Bioorganic and Medicinal Chemistry Letters

Volumn 21, Issue 10, 2011, Pages 2934-2936

  Solanki, Kusum ^a   Gupta, Munishwar Nath ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY DELHI   (India)

Author keywords

Chemical modification; Crosslinked protein coated microcrystals; Low water organic media; Pseudomonas cepacia lipase; Pyromellitic dianhydride; Transesterification reactions

Indexed keywords

ETHANE; ETHYLENE GLYCOL DIMETHYL ETHER; N,N DIMETHYLFORMAMIDE; OCTANE; ORGANIC SOLVENT; TRIACYLGLYCEROL LIPASE; UNCLASSIFIED DRUG;

ARTICLE; CRYSTAL; ENZYME ACTIVITY; ENZYME MODIFICATION; ENZYME STRUCTURE; PH; PRECIPITATION; TRANSESTERIFICATION; WATER CONTENT;

ACYLATION; BENZOATES; BURKHOLDERIA CEPACIA; CATALYSIS; DIMETHYLFORMAMIDE; ESTERIFICATION; ETHYL ETHERS; HYDROGEN-ION CONCENTRATION; LIPASE; MOLECULAR STRUCTURE; ORGANIC CHEMICALS; SOLVENTS;

BURKHOLDERIA CEPACIA;

EID: 79955554171     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2011.03.059     Document Type: Article

References (32)

1. E.N. Vulfson, P.J. Halling, and H.L. Holland Nonaqueous Solvents, Methods and Protocols 2001 Humana Press Inc. New Jersey
2. B. Hauer, and S.M. Roberts Curr. Opin. Chem. Biol. 8 2004 103
3. G. Carrea, and S. Riva Angew. Chem., Int. Ed. 39 2000 2226
4. A. Schmid, J.S. Dordick, A. Kiener, M. Wubbolts, and B. Witholt Nature 409 2001 258
5. M.N. Gupta Eur. J. Biochem. 203 1992 25
6. M.Y. Lee, and J.S. Dordick Curr. Opin. Biotechnol. 13 2002 376
7. M.N. Gupta, and I. Roy Eur. J. Biochem. 27 2004 2575
8. E.P. Hudson, R.K. Eppler, and D.S. Clark Curr. Opin. Biotechnol. 16 2005 637
9. A. Zaks, and A.M. Klibanov Proc. Natl. Acad. Sci. U.S.A. 82 1985 3192
10. D.G. Rees, I.I. Gerashchenko, E.V. Kudryashova, V.V. Mozhaev, and P.J. Halling Biocatal. Biotransform. 20 2002 161
11. V.V. Mozhaev, V.A. Šikšnis, N.S. Melik-Nubarov, N.Z. Galkantaite, G.J. Denis, E.P. Butkus, B.Yu. Zaslavsky, N.M. Mestechkina, and K. Martinek Eur. J. Biochem. 173 1988 147
12. K. Solanki, S. Shah, and M.N. Gupta Biocatal. Biotransform. 26 2008 258
13. n-Octane, DMF and 1,2-diemthoxyethane (anhydrous grade with water content less than 0.001% (v/v)) were obtained from Sigma Chemical (St. Louis, MO, USA). n-Propanol and tris(hydroxymethyl)aminomethane were obtained from Merck (Mumbai, India). PMDA was a product of Eastman Kodak Company (Rochester, NY, USA). P. cepacia lipase was a gift from Amano Enzyme Inc. (Nagoya, Japan). Tributyrin (>99%) was obtained from Himedia laboratories Pvt. Ltd. (Mumbai, India). Glutaraldehyde (25% w/v aqueous solution) was purchased from Merck (Hohenbrunn, Germany). All solvents were dried over molecular sieves before using. All other chemicals used were of analytical grade.
14. 11 PMDA solution prepared in dimethylsulfoxide (2 mM, 1 ml) was added dropwise at 4 °C to 0.04 mM enzyme solution (10 ml, prepared in 100 mM Tris-HCl buffer, pH 7.0) with stirring. The pH of the reaction was maintained at 7.0 using 20 mM NaOH. The reaction mixture was stirred for 2 h followed by its dialysis against 10 mM Tris-HCl buffer (pH 7.0).
15. M. Kreiner, B.D. Moore, and M.C. Parker Chem. Commun. 2001 1096
16. 15 except instead of n-propanol, 1,2-dimethoxyethane was used as precipitating and rinsing agent. The biocatalyst preparation was then rinsed thrice with corresponding dry organic solvent or organic solvent containing various amounts of water.
17. I. Roy, and M.N. Gupta Bioorg. Med. Chem. Lett. 14 2004 2191
18. S. Shah, and M.N. Gupta Biorg. Med. Chem. Lett. 17 2007 921
19. 18 (enzyme precipitated and rinsed with organic solvent).
20. S. Shah, A. Sharma, and M.N. Gupta Biocatal. Biotransform. 26 2008 266
21. Preparation of CLPCMC of lipase: The PCMC of lipase obtained were dispersed in 500 μl of 1,2-dimethoxyethane followed by addition of 10 μl of glutaraldehyde (25% v/v in water). The mixture was kept at 4 °C for 1 h with constant shaking at 300 rpm. The CLPCMC thus formed was then rinsed thrice with 1,2-dimethoxyethane followed by rinsing thrice with corresponding dry organic solvent or organic solvent containing various amounts of water and again centrifuged at 5000 g for 5 min at 4 °C to remove the organic solvents.
22. S.L. Synder, and P.Z. Sobocinski Anal. Biochem. 64 1975 284
23. W. Al-Azzam, E.A. Pastrana, Y. Ferrer, Q. Huang, R. Schweitzer-Stenner, and K. Griebenow Biophys. J. 83 2002 3637
24. A. Sugihara, M. Ueshima, Y. Shimada, S. Tsunasawa, and Y.J. Tominaga Biochemistry 112 1992 598
25. A.O. Triantafyllou, E. Wehtje, P. Adlercreutz, and B. Mattiasson Biotechnol. Bioeng. 45 1995 566
26. 25 Samples were taken at appropriate time intervals and analyzed by gas chromatography (GC).
27. 25
28. P. Jain, S. Jain, and M.N. Gupta Anal. Bioanal. Chem. 381 2005 1480
29. M.M. Bradford Anal. Biochem. 72 1976 248
30. M. Luic, S. Tuic, I. Lescic, E. Ljubovic, D. Sepac, V. Sunjic, L. Vitale, W. Saenger, and B. Kojic-Prodic Eur. J. Biochem. 268 2001 3964
31. C.H. Wong, S.T. Chen, W.J. Hennen, J.A. Bibbs, Y.-F. Wang, J.L.-C. Liu, M.W. Pantoliano, M. Whitlow, and P.N. Bryan J. Am. Chem. Soc. 112 1990 945
32. V.G.H. Eijsink, S. Gaseidnes, T.V. Borchert, and B. Van den Burg Biomol. Eng. 22 2005 21