Increasing the activity and enantioselectivity of lipases by sol-gel immobilization: Further advancements of practical interest

Nanoscale

Volumn 6, Issue 12, 2014, Pages 6220-6228

  Tielmann, Patrick ^a   Kierkels, Hans ^b   Zonta, Albin ^a   Ilie, Adriana ^a,c   Reetz, Manfred T ^a,c  

^a MAX PLANCK INSTITUT FÜR KOHLENFORSCHUNG   (Germany)

^b DSM RESEARCH   (Netherlands)

^c PHILIPPS UNIVERSITY MARBURG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ENANTIOSELECTIVITY; SILICATES; SOL-GEL PROCESS; SOL-GELS;

BURKHOLDERIA CEPACIA; HYDROPHOBIC SILICATE; KINETIC RESOLUTION; LIPASE IMMOBILIZATION; RECYCLING EXPERIMENTS; SECOND GENERATION; SOL-GEL ENTRAPMENT; SOL-GEL IMMOBILIZATION;

LIPASES;

IMMOBILIZED ENZYME; NANOPARTICLE; TRIACYLGLYCEROL LIPASE;

ADSORPTION; CHEMISTRY; CRYSTALLIZATION; ENZYME ACTIVATION; ENZYME SPECIFICITY; PHASE TRANSITION; PROCEDURES; ULTRASTRUCTURE;

ADSORPTION; CRYSTALLIZATION; ENZYME ACTIVATION; ENZYMES, IMMOBILIZED; LIPASE; NANOPARTICLES; PHASE TRANSITION; SUBSTRATE SPECIFICITY;

EID: 84901762882     PISSN: 20403364     EISSN: 20403372     Source Type: Journal    
DOI: 10.1039/c3nr06317h     Document Type: Review

References (94)

1. K. Drauz, H. Gröger and O. May, Enzyme Catalysis in Organic Synthesis, VCH, Weinheim, 3rd edn, 2012, vol. I-III
2. K. Faber, Biotransformations in Organic Chemistry, Springer, Berlin, 6th edn, 2011
3. A. Liese, K. Seelbach and C. Wandrey, Industrial Biotransformations, Wiley-VCH, Weinheim, 2006
4. M. T. Reetz J. Am. Chem. Soc. 2013 135 12480 12496
5. A. M. Klibanov Nature 2001 409 241 246
6. G. Carrea S. Riva Angew. Chem., Int. Ed. 2000 39 2226 2254
7. R. D. Schmid R. Verger Angew. Chem., Int. Ed. 1998 37 1608 1633
8. K.-E. Jaeger B. W. Dijkstra M. T. Reetz Annu. Rev. Microbiol. 1999 53 315 351
9. U. T. Bornscheuer and R. J. Kazlauskas, Hydrolases in Organic Synthesis: Regio- and Stereoselective Biotransformations, Wiley-VCH, Weinheim, Germany, 1999
10. S. Naik A. Basu R. Saikia B. Madan P. Paul R. Chaterjee J. Brask A. Svendsen J. Mol. Catal. B: Enzym. 2010 65 18 23
11. D. Sharma B. Sharma A. K. Shukla Biotechnology 2011 10 23 40
12. A. Baldessari Methods Mol. Biol. 2012 861 445 456
13. B. Andualema A. Gessesse Biotechnology 2012 11 100 118
14. A. Bassegoda S. Cesarini P. Diaz Comput. Struct. Biotechnol. J. 2012 2 e201209005
15. X. Song X. Qi B. Hao Y. Qu Eur. J. Lipid Sci. Technol. 2008 110 1095 1101
16. M. Paravidino, P. Böhm, H. Gröger and U. Hanefeld, Hydrolysis and Formation of Carboxylic Acid Esters, in Enzyme Catalysis in Organic Synthesis, ed., K. Drauz, H. Gröger, and, O. May, Wiley-VCH, Weinheim, Germany, 3rd edn, 2012, pp. 251-362
17. F. Balkenhohl K. Ditrich B. Hauer W. Ladner J. Prakt. Chem. 1997 339 381 384
18. A. M. Brzozowski U. Derewenda Z. S. Derewenda G. G. Dodson D. M. Lawson J. P. Turkenburg F. Bjorkling B. Huge-Jensen S. A. Patkar L. Thim Nature 1991 351 491 494
19. H. van Tilbeurgh M.-P. Egloff C. Martinez N. Rugani R. Verger C. Cambillau Nature 1993 362 81 820
20. J. M. Guisan, Immobilization of Enzymes and Cells; Methods in Molecular Biology, Springer, New York, 3rd edn, 2013, vol. 1051
21. D. Avnir S. Braun O. Lev M. Ottolenghi Chem. Mater. 1994 6 1605 1614
22. P. Johnson T. L. Whateley J. Colloid Interface Sci. 1971 37 557 563
23. M. Glad O. Norrlöw B. Sellergren N. Siegbahn K. Mosbach J. Chromatogr. 1985 347 11 23
24. D. Avnir Acc. Chem. Res. 1995 28 328 334
25. D. Avnir T. Coradin O. Lev J. Livage J. Mater. Chem. 2006 16 1013 1030
26. L. L. Hench J. K. West Chem. Rev. 1990 90 33 72
27. C. J. Brinker and G. W. Scherer, Sol-Gel Science: The Physics and Chemistry of Sol-Gel Processing, Academic Press, Boston, 1990
28. M. T. Reetz A. Zonta J. Simpelkamp Angew. Chem., Int. Ed. Engl. 1995 34 301 303
29. M. T. Reetz A. Zonta J. Simpelkamp Biotechnol. Bioeng. 1996 49 527 534
30. M. T. Reetz A. Zonta J. Simpelkamp W. Könen Chem. Commun. 1996 1397 1398
31. M. T. Reetz Adv. Mater. 1997 9 943 954
32. J. Livage C. R. Acad. Sci., Ser. IIb: Mec., Phys., Chim., Astron. 1996 322 417 427
33. I. Gill Chem. Mater. 2001 13 3404 3421
34. W. Jin J. D. Brennan Anal. Chim. Acta 2002 461 1 36
35. A. C. Pierre Biocatal. Biotransform. 2004 22 145 170
36. M. T. Reetz, Practical Protocols for Lipase Immobilization via Sol-Gel Techniques, in Immobilization of Enzymes and Cells; Methods in Molecular Biology, ed., J. M. Guisan, Springer, New York, 3rd edn, 2013, vol. 1051, pp. 241 254
37. D. N. Reinhoudt A. M. Eendebak W. F. Nijenhuis W. Verboom M. Kloosterman H. E. Schoemaker J. Chem. Soc., Chem. Commun. 1989 399 400
38. D.-J. van Unen J. F. J. Engbersen D. N. Reinhoudt Biotechnol. Bioeng. 2002 77 248 255
39. K. Griebenow Y. D. Laureano A. M. Santos I. M. Clemente L. Rodríguez M. W. Vidal G. Barletta J. Am. Chem. Soc. 1999 121 8157 8163
40. Y. L. Khmelnitsky S. H. Welch D. S. Clark J. S. Dordick J. Am. Chem. Soc. 1994 116 2647 2648
41. Y.-Y. Liu J.-H. Xu Y. Hu J. Mol. Catal. B: Enzym. 2000 10 523 529
42. F. Theil Tetrahedron 2000 56 2905 2919
43. M. T. Reetz P. Tielmann W. Wiesenhöfer W. Könen A. Zonta Adv. Synth. Catal. 2003 345 717 728
44. K. Mori Tetrahedron 1989 45 3233 3298
45. K. Mori H. Kikuchi Liebigs Ann. Chem. 1989 1267 1269
46. S. Liang L. A. Paquette Tetrahedron: Asymmetry 1990 1 445 452
47. S.-L. Chen Q.-H. Hu T.-P. Loh Org. Lett. 2004 6 3365 3367
48. A. Arnone P. Bravo W. Panzeri F. Viani M. Zanda Eur. J. Org. Chem. 1999 117 127
49. S. G. Davies G. D. Smyth J. Chem. Soc., Perkin Trans. 1 1996 2467 2477
50. S. G. Davies G. D. Smyth Tetrahedron: Asymmetry 1996 7 1005 1006
51. A. Belan J. Bolte A. Fauve J. G. Gourcy H. Veschambre J. Org. Chem. 1987 52 256 260
52. T. M. Stokes A. C. Oehlschlager Tetrahedron Lett. 1987 28 2091 2094
53. T. Sugai O. Katoh H. Ohta Tetrahedron 1995 51 11987 11998
54. E. Vänttinen L. T. Kanerva Tetrahedron: Asymmetry 1995 6 1779 1786
55. F. Secundo G. Ottolina S. Riva G. Carrea Tetrahedron: Asymmetry 1997 8 2167 2173
56. Y. Kita Y. Takebe S. Murata T. Naka S. Akai Tetrahedron Lett. 1996 37 7369 7372
57. Y. Kita Y. Takebe K. Murata T. Naka S. Akai J. Org. Chem. 2000 65 83 88
58. K. Nakamura M. Kinoshita A. Ohno Tetrahedron 1995 51 8799 8808
59. C.-S. Chen C. J. Sih Angew. Chem., Int. Ed. Engl. 1989 28 695 707
60. P. Tielmann, Dr. rer. nat. thesis, Ruhr-Universität Bochum, Germany, 2002
61. B. Tamburini, A. Perboni, T. Rossi, D. Donati, D. Andreotti, G. Gaviraghi, R. Carleso and C. Bismara, EP0416953A2, 1991
62. B. Tamburini, T. Rossi, D. Donati, G. Gaviraghi and G. Tarzi, Recent Advances in the Chemistry of Anti-Infective Agents, ed., P. H. Bently, and, R. Ponsford, Royal Society of Chemistry, Cambridge, 1993, pp. 21-35
63. K. E. Laumen D. Breitgoff R. Seemayer M. P. Schneider J. Chem. Soc., Chem. Commun. 1989 148 150
64. H. Hönig P. Seufer-Wasserthal Synthesis 1990 1137 1140
65. D. Basavaih P. R. Krishna Tetrahedron 1994 50 10521 10530
66. P. Stead H. Marley M. Mahmoudian G. Webb D. Noble Y. T. Ip E. Piga T. Rossi S. Roberts M. J. Dawson Tetrahedron: Asymmetry 1996 7 2247 2250
67. P. M. Jackson S. M. Roberts S. Davalli D. Donati C. Marchiroro A. Perboni S. Proviera T. Rossi J. Chem. Soc., Perkin Trans. 1 1996 2029 2030
68. S. Nanda A. I. Scott J. Mol. Catal. B: Enzym. 2004 30 1 12
69. A. Tomin D. Weiser G. Hellner Z. Bata L. Corici F. Péter B. Koczba L. Poppe Process Biochem. 2011 46 52 58
70. D. Weiser Z. Boros G. Hornyanszky A. Toth L. Poppe Process Biochem. 2012 47 428 434
71. H. Noureddini X. Gao R. S. Philkana Bioresour. Technol. 2005 96 769 777
72. A. Ursoiu C. Paul C. Marcu F. Peter World Acad. Sci. Eng. Tech. 2011 76 70 74
73. S. Sayin E. Yilmaz M. Yilmaz Org. Biomol. Chem. 2011 9 4021 4024
74. E. Yilmaz M. Sezgin Appl. Biochem. Biotechnol. 2012 166 1927 1940
75. M. Päiviö P. Perkiö L. T. Kanerva Tetrahedron: Asymmetry 2012 23 230 236
76. J. Hetfleijs G. Kuncova S. Sabata V. Blechta J. Brus J. Sol-Gel Sci. Technol. 2006 38 121 131
77. R. C. Pinheiro C. M. F. Soares O. A. A. dos Santos H. F. de Castro F. F. de Moraes G. M. Zanin J. Mol. Catal. B: Enzym. 2008 52-53 27 33
78. P. Hara U. Hanefeld L. T. Kanerva J. Mol. Catal. B: Enzym. 2008 50 80 86
79. J. Brem M. C. Turcu C. Paizs K. Lundell M.-I. Toşa F.-D. Irimie L. T. Kanerva Process Biochem. 2012 47 119 126
80. M. Stoytcheva, G. Montero, L. Toscano, V. Gochev and B. Valdez, The Immobilized Lipases in Biodiesel Production, in Biodiesel-Feedstocks and Processing Technologies, ed., M. Stoytcheva, and, G. Montero, InTech, Croatia, Rijeka, 2011, pp. 397-410
81. P. Adlercreutz Chem. Soc. Rev. 2013 42 6406 6436
82. R. A. Sheldon S. van Pelt Chem. Soc. Rev. 2013 42 6223 6235
83. S. Furukawa T. Ono H. Ijima K. Kawakami J. Mol. Catal. B: Enzym. 2002 17 23 28
84. X. Cao J. Yang L. Shu B. Yu Y. Yan Process Biochem. 2009 44 177 182
85. G. Kuncova J. Szilva J. Hetflejs S. Sabata J. Sol-Gel Sci. Technol. 2003 26 1183 1187
86. A. Tomin G. Hornyánszky K. Kupai Z. Dorkó L. Ürge F. Darvas L. Poppe Process Biochem. 2010 45 859 865
87. M. T. Reetz W. Wiesenhöfer G. Francio W. Leitner Chem. Commun. 2002 992 993
88. M. T. Reetz A. Zonta V. Vijayakrishnan K. Schimossek J. Mol. Catal. A: Chem. 1998 134 251 258
89. M. T. Reetz R. Wenkel D. Avnir Synthesis 2000 781 783
90. M. T. Reetz Angew. Chem., Int. Ed. 2011 50 138 174
91. A. G. Sandström Y. Wikmark K. Engström J. Nyhlen J.-E. Bäckvall Proc. Natl. Acad. Sci. U. S. A. 2012 109 78 83
92. Q. Wu P. Soni M. T. Reetz J. Am. Chem. Soc. 2013 135 1872 1881
93. A. Svendsen Biochim. Biophys. Acta 2000 1543 223 238
94. T. Ema T. Fujii M. Ozaki T. Korenaga T. Sakai Chem. Commun. 2005 4650 4651