Enantioselective acetylation of (R,S)-atenolol: The use of Candida rugosa lipases immobilized onto magnetic chitosan nanoparticles in enzyme-catalyzed biotransformation

Journal of Molecular Catalysis B: Enzymatic

Volumn 134, Issue , 2016, Pages 43-50

  Sikora, Adam ^a   Chełminiak Dudkiewicz, Dorota ^b   Siódmiak, Tomasz ^a   Tarczykowska, Agata ^a   Sroka, Wiktor Dariusz ^a   Ziegler Borowska, Marta ^b   Marszałł, Michał Piotr ^a  

^a NICOLAUS COPERNICUS UNIVERSITY   (Poland)

^b NICOLAUS COPERNICUS UNIVERSITY   (Poland)

Author keywords

(R,S) atenolol; Enantioselective acetylation; Lipase; Magnetic nanoparticles

Indexed keywords

ACETYLATION; CANDIDA; CATALYST ACTIVITY; CHITIN; CHITOSAN; ENANTIOSELECTIVITY; ENZYME IMMOBILIZATION; ENZYMES; MAGNETISM; NANOMAGNETICS; NANOPARTICLES; YEAST;

ATENOLOL; CANDIDA RUGOSA LIPASE; CHITOSAN DERIVATIVES; ENANTIOMERIC EXCESS; ENANTIOSELECTIVE; IMMOBILIZATION PROTOCOLS; LIPASE FROM CANDIDA RUGOSA; MAGNETIC NANO-PARTICLES;

LIPASES;

EID: 84988410967     PISSN: 13811177     EISSN: 18733158     Source Type: Journal    
DOI: 10.1016/j.molcatb.2016.09.017     Document Type: Article

References (34)

1. [1] Siodmiak, T., Mangelings, D., Vander Heyden, Y., Ziegler-Borowska, M., Marszall, M.P., High enantioselective novozym 435-catalyzed esterification of (R,S)-flurbiprofen monitored with a chiral stationary phase. Appl. Biochem. Biotechnol. 175:5 (2015), 2769–2785.
2. [2] Saxena, R.K., Ghosh, P.K., Gupta, R., Davidson, W.S., Bradoo, S., Gulati, R., Microbial lipases: potential biocatalysts for the future industry. Curr. Sci. 77:1 (1999), 101–115.
3. [3] Sabuzi, F., Churakova, E., Galloni, P., Wever, R., Hollmann, F., Floris, B., Conte, V., Thymol bromination—a comparison between enzymatic and chemical catalysis. Eur. J. Inorg. Chem. 21 (2015), 3519–3525.
4. [4] Sikora, A., Siodmiak, T., Marszall, M.P., Kinetic resolution of profens by enantioselective esterification catalyzed by Candida antarctica and Candida rugosa lipases. Chirality 26:10 (2014), 663–669.
5. [5] Siodmiak, T., Ruminski, J.K., Marszall, M.P., Application of lipases from Candida rugosa in the enantioselective esterification of (R,S)-ibuprofen. Curr. Org. Chem. 16:8 (2012), 972–977.
6. [6] Barbosa, O., Ariza, C., Ortiz, C., Torres, R., Kinetic resolution of (R/S)-propranolol (1-isopropylamino-3-(1-naphtoxy)-2-propanolol) catalyzed by immobilized preparations of Candida antarctica lipase B (CAL-B). New Biotechnol. 27:6 (2010), 844–850.
7. [7] Contesini, F.J., Carvalho, P.d.O., Esterification of (RS)-ibuprofen by native and commercial lipases in a two-phase system containing ionic liquids. Tetrahedron: Asymmetry 17:14 (2006), 2069–2073.
8. [8] Carvalho, P.d.O., Contesini, F.J., Ikegaki, M., Enzymatic resolution of (R,S)-ibuprofen and (R,S)-ketoprofen by microbial lipases from native and commercial sources. Braz. J. Microbiol. 37:3 (2006), 329–337.
9. [9] Ong, A.L., Kamaruddin, A.H., Bhatia, S., Aboul-Enein, H.Y., Enantioseparation of (R,S)-ketoprofen using Candida antarctica lipase B in an enzymatic membrane reactor. J. Sep. Sci. 31:13 (2008), 2476–2485.
10. [10] Wu, J.C., Low, H.R., Leng, Y., Chow, Y., Li, R., Talukder, M.M.R., Choi, W.J., Ketoprofen resolution by enzymatic esterification and hydrolysis of the ester product. Biotechnol. Bioproc.: E. 11:3 (2006), 211–214.
11. [11] Chen, C.S., Fujimoto, Y., Girdaukas, G., Sih, C.J., Quantitative-analyses of biochemical kinetic resolutions of enantiomers. J. Am. Chem. Soc. 104:25 (1982), 7294–7299.
12. [12] Xie, W.L., Wang, J.L., Enzymatic production of biodiesel from soybean oil by using immobilized lipase on Fe3O4/poly(styrene-rnethacrylic acid) magnetic microsphere as a biocatalyst. Energy Fuels 28:4 (2014), 2624–2631.
13. [13] Xie, W.L., Wang, J.L., Immobilized lipase on magnetic chitosan microspheres for transesterification of soybean oil. Biomass Bioenergy 36 (2012), 373–380.
14. [14] Bayramoglu, G., Arica, M.Y., Preparation of poly (glycidylmethacrylate-methylmethacrylate) magnetic beads: application in lipase immobilization. J. Mol. Catal. B: Enzym. 55:1–2 (2008), 76–83.
15. [15] Mateo, C., Palomo, J.M., Fernandez-Lorente, G., Guisan, J.M., Fernandez-Lafuente, R., Improvement of enzyme activity, stability and selectivity via immobilization techniques. Enzyme Microb. Technol. 40:6 (2007), 1451–1463.
16. [16] Ziegler-Borowska, M., Chelminiak, D., Siodmiak, T., Sikora, A., Marszall, M.P., Kaczmarek, H., Synthesis of new chitosan coated magnetic nanoparticles with surface modified with long-distanced amino groups as a support for bioligands binding. Mater. Lett. 132 (2014), 63–65.
17. [17] Ling, D., Lee, N., Hyeon, T., Chemical synthesis and assembly of uniformly sized iron oxide nanoparticles for medical applications. Acc. Chem. Res. 48:5 (2015), 1276–1285.
18. [18] Moaddel, R., Marszall, M.P., Bighi, F., Yang, Q., Duan, X., Wainer, I.W., Automated ligand fishing using human serum albumin-coated magnetic beads. Anal. Chem. 79:14 (2007), 5414–5417.
19. [19] Siodmiak, T., Ziegler-Borowska, M., Marszall, M.P., Lipase-immobilized magnetic chitosan nanoparticles for kinetic resolution of (R,S)-ibuprofen. J. Mol. Catal. B: Enzym. 94 (2013), 7–14.
20. [20] Zhang, D.-H., Yuwen, L.-X., Xie, Y.-L., Li, W., Li, X.-B., Improving immobilization of lipase onto magnetic microspheres with moderate hydrophobicity/hydrophilicity. Colloids Surf. B: Biointerfaces 89 (2012), 73–78.
21. [21] Liu, X.Q., Guan, Y.P., Shen, R., Liu, H.Z., Immobilization of lipase onto micron-size magnetic beads. J. Chromatogr. B: Anal. Technol. Biomed. Life Sci. 822:1–2 (2005), 91–97.
22. [22] Yucel, Y., Biodiesel production from pomace oil by using lipase immobilized onto olive pomace. Bioresour. Technol. 102:4 (2011), 3977–3980.
23. [23] Xie, W.L., Zang, X.Z., Immobilized lipase on core-shell structured Fe3O4-MCM-41 nanocomposites as a magnetically recyclable biocatalyst for interesterification of soybean oil and lard. Food Chem. 194 (2016), 1283–1292.
24. [24] Carlberg, B., Samuelsson, O., Lindholm, L.J., Atenolol in hypertension: is it a wise choice?. Lancet 364:9446 (2004), 1684–1689.
25. [25] Dwivedee, B.P., Ghosh, S., Bhaumik, J., Banoth, L., Banerjee, U.C., Lipase-catalyzed green synthesis of enantiopure atenolol. RSC Adv. 5:21 (2015), 15850–15860.
26. [26] Zelaszczyk, D., Kiec-Kononowicz, K., Biocatalytic approaches to optically active beta-blockers. Curr. Med. Chem. 14:1 (2007), 53–65.
27. [27] Escorcia, A.M., Molina, D., Daza, M.C., Doerr, M., Acetylation of (R,S)-propranolol catalyzed by Candida antarctica lipase B: an experimental and computational study. J. Mol. Catal. B: Enzym. 98 (2013), 21–29.
28. [28] Narina, S.V., Sudalai, A., Enantioselective synthesis of (S)-timolol via kinetic resolution of terminal epoxides dihydroxylation of allylamines (vol 63, pg. 3026, 2007). Tetrahedron, 63(29), 2007, 6938.
29. [29] Ziegler-Borowska, M., Chelminiak, D., Kaczmarek, H., Kaczmarek-Kedziera, A., Effect of side substituents on thermal stability of the modified chitosan and its nanocomposites with magnetite. J. Therm. Anal. Calorim. 124:3 (2016), 1267–1280.
30. [30] Zhu, Y.T., Ren, X.Y., Liu, Y.M., Wei, Y., Qing, L.S., Liao, X., Covalent immobilization of porcine pancreatic lipase on carboxyl-activated magnetic nanoparticles: characterization and application for enzymatic inhibition assays. Mater. Sci. Eng. C: Mater. Biol. Appl. 38 (2014), 278–285.
31. [31] Osuna, Y., Sandoval, J., Saade, H., Lopez, R.G., Martinez, J.L., Colunga, E.M., de la Cruz, G., Segura, E.P., Arevalo, F.J., Zon, M.A., Fernandez, H., Ilyina, A., Immobilization of Aspergillus niger lipase on chitosan-coated magnetic nanoparticles using two covalent-binding methods. Bioprocess Biosyst. Eng. 38:8 (2015), 1437–1445.
32. [32] Velasco-Lozano, S., Lopez-Gallego, F., Rocha-Martin, J., Guisan, J.M., Favela-Torres, E., Improving enantioselectivity of lipase from Candida rugosa by carrier-bound and carrier-free immobilization. J. Mol. Catal. B: Enzym. 130 (2016), 32–39.
33. [33] Mukherjee, J., Gupta, M.N., Lipase coated clusters of iron oxide nanoparticles for biodiesel synthesis in a solvent free medium. Bioresour. Technol. 209 (2016), 166–171.
34. [34] Xie, W.L., Ma, N., Immobilized lipase on Fe3O4 nanoparticles as biocatalyst for biodiesel production. Energy Fuels 23 (2009), 1347–1353.