Catalytic effect of calix[n]arene based sol-gel encapsulated or covalent immobilized lipases on enantioselective hydrolysis of (R/S)-naproxen methyl ester

Journal of Inclusion Phenomena and Macrocyclic Chemistry

Volumn 72, Issue 1-2, 2012, Pages 189-196

  Erdemir, Serkan ^a   Yilmaz, Mustafa ^a  

^a SELCUK UNIVERSITY   (Turkey)

Author keywords

Calixarenes; Enantioselectivity; Naproxene; Silica; Sol gel

Indexed keywords

EID: 84862155186     PISSN: 09230750     EISSN: None     Source Type: Journal    
DOI: 10.1007/s10847-011-9962-1     Document Type: Article

References (46)

1. Benjamin, S., Pandey, A.: Candida rugosa lipases: molecular biology and versatility in biotechnology. Yeast 14, 1069 (1998)
2. Bornscheuer, U.T., Kazlanskas, R.J.: Hydrolases in Organic Syntheses Regio- and Stereoselective Biotransformations. Wiley- VCH, Weinheim (1999)
3. Collins, A.N., Sheldrake, G.N., Crosby, J.: Chirality in Industry, vol. II. Developments in the Manufacture and Applications of Optically Active Compounds. Wiley, New York (1997)
4. Secundo, F., Carrea, G.: Lipase activity and conformation in neat organic solvents. J. Mol. Catal. B: Enzymatic 19-20, 93-102 (2002) (Pubitemid 35304723)
5. Cao, L., Van Langen, L., Sheldon, R.A.: Immobilised enzymes: carrier-bound or carrier-free? Curr. Opin. Biotechnol. 14, 387-394 (2003) (Pubitemid 37011318)
6. Brinker, C.J., Scherer, G.W.: Sol-Gel Science: The Physics and Chemistry of Sol-Gel Processing. Academic Press, Boston (1990)
7. Glad, M., Norrlow, O., Sellergren, B., Siegbahn, N., Mosbach, K.: Use of silane monomers for molecular imprinting and enzyme entrapment in polysiloxane-coated porous silica. J. Chromatogr. A 347, 11-23 (1985)
8. Venton, D.L., Cheesman, K.L., Chatterton, R.T., Anderson, T.L.: Entrapment of a highly specific antiprogesterone antiserum using polysiloxane copolymers. Biochim. Biophys. Acta 797, 343-347 (1984) (Pubitemid 14194899)
9. Chevalier, Y.: New surfactants: new chemical functions and molecular architectures. Curr. Opin. Colloid Interface Sci. 7, 3-11 (2002) (Pubitemid 34605960)
10. Coradin, T., Lopez, P.J.: Biogenic silica patterning: simple chemistry or subtle biology? Chem. Biol. Chem. 4, 251-259 (2003) (Pubitemid 36505194)
11. Reetz, M.T., Tielmann, P., Wisenhofer, W., Konen, W., Zonta, A.: Second generation sol-gel encapsulated lipases: robust heterogeneous biocatalysts. Adv. Synth. Catal. 345, 717-728 (2003) (Pubitemid 37406649)
12. Zhou, Y., Schatka, J.H., Antonietti, M.: Room-temperature ionic liquids as template to monolithic mesoporous silica with wormlike pores via a sol-gel nanocasting technique. Nano Lett. 4, 477-481 (2004) (Pubitemid 38402636)
13. Reetz, M.T., Zonta, A., Simplekamp, J.: Efficient immobilization of lipases by entrapment in hydrophobic sol-gel materials. Bio-technol. Bioeng. 49, 527-534 (1996) (Pubitemid 26062610)
14. Luckarift, H.R., Spain, J.C., Naik, R.R., Stone, M.O.: Enzyme immobilization in a biomimetic silica support. Nat. Biotechnol. 22, 211-213 (2004) (Pubitemid 38160537)
15. Sun, Q., Vrieling, E.G., van Santen, R.A., Sommerdikj, N.A.J.M.: Bioinspired synthesis of mesoporous silicas. Curr. Opin. Solid State Mater. Sci. 8, 111-120 (2004) (Pubitemid 40134559)
16. Bassindale, A.R., Brandstadt, K.F., Lane, T.H., Taylor, P.G.: Biocatalysis of siloxane bonds. Polym. Preprints 44, 570-571 (2003)
17. Cha, J.N., Shimizu, K., Zhou, Y., Christiansen, S.C., Chmelka, B.F., Stucky, G.D., Morse, D.E.: Silicatein a: cathepsin L-like protein in sponge biosilica. Proc. Natl. Acad. Sci. 96, 361-365 (1999)
18. Bohmer, V.: Calixarenes, macrocycles with (almost) unlimited possibilities. Angew. Chem. Int. Ed. Engl. 34, 713-745 (1995)
19. Asfari, Z., Bohmer, V., Harrowfield, J., Vicans, J.: Calixarenes 2001, pp. 71-88. Kluwer, Dordrecht (2001)
20. Gokel, G.W.: Crown Ethers and Cryptands, pp. 66-73. Royal Society of Chemistry, Cambridge (1991)
21. Wenz, G.: Cyclodextrins as building blocks for supramolecular structures and functional units. Angew. Chem. Int. Ed. Engl. 33, 803-822 (1994) (Pubitemid 24986848)
22. Yilmaz, M., Memon, S., Tabakci, M., Bartsch, R.A.: Design of polymer appended calixarenes as ion carriers. In: Bregg, R.K. (ed.) New Frontiers in Polymer Research. Nova Publishers, NewYork (2006)
23. Gutsche, C.D., Iqbal, M., Stewart, D.: Calixarenes. 18. Synthesis procedures for p-tert-butylcalix[4]arene. J. Org. Chem. 51, 742-745 (1986)
24. Erdemir, S., Tabakci, M., Yilmaz, M.: Synthesis and chiral recognition abilities of new calix[6]arenes bearing amino alcohol moieties. Tetrahedron Asymmetr. 17, 1258-1263 (2006) (Pubitemid 43776352)
25. Memon, S., Akceylan, E., Sap, B., Tabakci, M., Roundhill, D.M., Yilmaz, M.: Polymer supported calix[4]arene derivatives for the extraction of metals and dichromate anions. J. Polym. Environ. 11, 67-74 (2003) (Pubitemid 38149298)
26. Erdemir, S., Yilmaz, M.: Synthesis of calix[n]arene-based silica polymers for lipase immobilization. J. Mol. Catal. B: Enzym. 58, 29-35 (2009)
27. Wu, J.Y., Liu, S.W.: Influence of alcohol concentration on lipase-catalyzed enantioselective esterification of racemic naproxen in isooctane: under controlled water activity. Enzyme Microb. Tech. 26, 124-130 (2000)
28. Takac, S., Bakkal, M.: Impressive effect of immobilization conditions on the catalytic activity and enantioselectivity of Candida rugosa lipase toward S-naproxen production. Process Biochem 42, 1021-1027 (2007) (Pubitemid 46702769)
29. Bradford, M.M.A.: A rapid and sensitive method for the quanti-tation of microgram quantities of protein utilizing the principle of protein-dye binding. Anal. Biochem. 72, 248-254 (1976)
30. Chiou, S.H., Wu, W.T.: Immobilization of Candida rugosa lipase on chitosan with activation of the hydroxyl groups. Biomaterials 25, 197-204 (2004)
31. Johri, S., Verma, V., Parshad, R., Koul, S., Taneja, S.C., Qazi, G.N.: Purification and characterisation of an ester hydrolase from a strain of Arthrobacter species: Its application in asymmetrisa-tion of 2-benzyl-1,3-propanediol acylates. Bioorg. Med. Chem. 9, 269-273 (2001) (Pubitemid 32244026)
32. Sahin, O., Erdemir, S., Uyanik, A., Yilmaz, M.: Enantioselective hydrolysis of (R/S)-naproxen methyl ester with sol-gel encapsulated lipase in presence of calix[n]arene derivatives. Appl. Catal. A: Gen. 369, 36-41 (2009)
33. Chen, C.S., Fujimoto, Y., Girdaukas, G., Sih, C.J.: Quantitative analyses of biochemical kinetic resolutions of enantiomers. J. Am. Chem. Soc. 104, 7294-7299 (1982)
34. Reinhoudt, D.N., Eendebak, A.M., Nijenhuis, W.F., Verboom, W., Kloosterman, M., Schoemaker, H.E.J.: The effect of crown ethers on enzyme-catalyzed reactions in organic solvents. Chem. Soc. Chem. Commun. 399-400 (1989)
35. Griebenow, K., Laureano, Y.D., Santos, A.M., Clemente, I.M., Rodriguez, L., Vidal, M.W., Barletta, G.: Improved enzyme activity and enantioselectivity in organic solvents by methyl-P-cyclodextrin. J. Am. Chem. Soc. 121, 8157-8163 (1999)
36. Khmelnitsky, Y.L., Welch, S.H., Clark, D.S., Dordick, J.S.: Salts dramatically enhance activity of enzymes suspended in organic solvents. J. Am. Chem. Soc. 116, 2647-2648 (1994)
37. Liu, Y.Y., Xu, J.H., Hu, Y.: Enhancing effect of Tween-80 on lipase performance in enantioselective hydrolysis of ketoprofen ester. J. Mol. Catal. B: Enzym 10, 523-529 (2000) (Pubitemid 30628638)
38. Gutsche, C.D.: Calixarenes Revisited. The Royal Society of Chemistry, Cambridge (1998)
39. Asfari, Z., Bohmer, V., Harrowfield, J., Vicens, J.: Calixarenes 2001, pp. 199-218. Kluwer, Dordrecht (2001)
40. Oshima, T., Sato, M., Shikaze, Y., Ohto, K., Inoue, K., Baba, Y.: Enzymatic polymerization of o-phenylendiamine with cyto-chrome c activated by a calixarene derivative in organic media. Biochem. Eng. J. 35, 66-70 (2007) (Pubitemid 46590822)
41. Oshima, T., Suetsugu, A., Baba, Y., Shikaze, Y., Ohto, K., Inoue, K.: Liquid membrane transport of cytochrome c using a calix[6]arene carboxylic acid derivative as a carrier. J. Membr. Sci. 307, 284-291 (2008) (Pubitemid 350256907)
42. Norde, W.: Adsorption of proteins from solution at the solidliquid interface. Adv. Colloid Interfac. 25, 267-340 (1986)
43. Wu, J.C., Selvam, V., Teo, H.H., Chow, Y., Talukder, M.M.R., Choi, W.J.: Immobilization of Candida rugosa lipase by cross-linking with glutaraldehyde followed by entrapment in alginate beads. Biocatal. Biotransform. 24, 352-357 (2006) (Pubitemid 44615047)
44. Liu, X., Guan, Y., Shen, R., Liu, H.: Immobilization of lipase onto micron-size magnetic beads. J. Chromatogr. B 822, 91-97 (2005) (Pubitemid 40994039)
45. Villeneuve, P., Muderhwa, J.M., Graille, J.M., Haas, M.J.: Customizing lipases for biocatalysis: a survey of chemical, physical and molecular biological approaches. J. Mol. Catal. B Enzym. 9, 113-148 (2000) (Pubitemid 30195728)
46. Huang, X.J., Ge, D., Xu, Z.K.: Preparation and characterization of stable chitosan nanofibrous membrane for lipase immobilization. Eur. Polym. J. 43, 3710-3718 (2007) (Pubitemid 47332449)