Improvement of Lipase Catalytic Properties by Immobilization in Hybrid Matrices
Lipases are enzymes particularly amenable for
immobilization by entrapment methods, as they can work equally
well in aqueous or non-conventional media and long-time stability of
enzyme activity and enantioselectivity is needed to elaborate more
efficient bioprocesses. The improvement of Pseudomonas
fluorescens (Amano AK) lipase characteristics was investigated by
optimizing the immobilization procedure in hybrid organic-inorganic
matrices using ionic liquids as additives. Ionic liquids containing a
more hydrophobic alkyl group in the cationic moiety are beneficial
for the activity of immobilized lipase. Silanes with alkyl- or aryl
nonhydrolizable groups used as precursors in combination with
tetramethoxysilane could generate composites with higher
enantioselectivity compared to the native enzyme in acylation
reactions of secondary alcohols. The optimal effect on both activity
and enantioselectivity was achieved for the composite made from
octyltrimethoxysilane and tetramethoxysilane at 1:1 molar ratio (60%
increase of total activity following immobilization and enantiomeric
ratio of 30). Ionic liquids also demonstrated valuable properties as
reaction media for the studied reactions, comparable with the usual
organic solvent, hexane.
[1] European Technology Platform on Sustainable Chemistry (2007, May)
Industrial or white biotechnology: a driver of sustainable growth in
Europe. Available: http://www.europabio.org/TPWhite/IB_Vision.pdf.
[2] M. Breuer, K. Ditrich, T. Habicher, B. Hauer, M. Kesseler, R. St├╝rmer,
T. Zelinski, ÔÇ×Industrial methods for the production of optically active
intermediates", Angew. Chem. Int. Ed., vol. 43, nr. 7, pp. 788-824, 2004.
[3] K. Buchholz, V. Kasche, U.T. Bornscheuer, Biocatalysts and enzyme
technology, Weinheim: Wiley-VCH Verlag, 2004, pp. 197-279.
[4] C. Mateo, J.M. Palomo, G. Fernandez-Lorente, J.M. Guisan, R.
Fernandez-Lafuente, "Improvement of enzyme activity, stability and
selectivity via immobilization techniques", Enzyme Microb. Technol.,
vol. 40, pp. 1451-1463, 2007.
[5] L. Cao, Carrier-bound immobilized enzymes: principles, applications
and design, Weinheim: Wiley-VCH, Verlag, 2005, pp. 16-36.
[6] R.A. Sheldon, "Enzyme immobilization: the quest for optimum
performance", Adv. Synth. Catal., vol 349, pp. 1289-1307, 2007.
[7] L. Betancor, H.R. Luckarift, "Bioinspired enzyme encapsulation for
biocatalysis", Trends Biotechnol., vol. 26, nr. 10, pp. 566-572, 2008.
[8] J. Livage, T. Coradin, C. Roux, ÔÇ×Encapsulation of biomolecules in silica
gels", J. Phys.: Condens. Matter, vol. 13, pp. 673-691, 2001.
[9] M.T. Reetz, P. Tielmann, W. Wiesenhöfer, W. Könen, A. Zonta,
ÔÇ×Second generation sol-gel encapsulated lipases: robust heterogeneous
biocatalysts", Adv. Synth. Catal., vol. 345, pp. 717-728, 2003.
[10] F. Peter, L. Poppe, C. Kiss, E. Szocs-Bir├│, G. Preda, C. Zarcula, A.
Olteanu, "Influence of precursors and additives on microbial lipases
stabilized by sol-gel entrapment", Biocat. Biotrans., vol. 23, nr. 3/4, pp.
251-260, 2005.
[11] A.C. Pierre, "The sol-gel encapsulation of biocatalysts", Biocat.
Biotrans., vol. 22, nr.3, pp. 145-170, 2004.
[12] S.H. Lee, T.T.N. Doan, S.H. Ha, W.-J Chang, Y.-M Koo, "Influence of
ionic liquids as additives on sol-gel immobilized lipase", J. Mol. Cat. B:
Enzymatic., vol. 47 pp. 129-134, 2007.
[13] C. Kiss, C. Zarcula, C. Csunderlik, F. Peter, "Enantioselective acylation
of secondary alcohols by biocatalysis with sol-gel immobilized
Pseudomonas fluorescens lipase, Rev. Chim. (Bucharest), vol. 58, nr. 8,
pp. 799-804, 2007.
[14] G. C.-S Chen. Y. Fujimoto, G. Girdauskas, C.J. Sih, "Quantitative
analyses of biochemical kinetic resolutions of enantiomers", J. Am.
Chem. Soc., vol. 104, pp. 7294-7299, 1982.
[15] F.Van Rantwijk, R.M. Lau, R.A. Sheldon, "Biocatalytic transformations
in ionic liquids", Trends Biotechnol., vol, 21, pp. 131-138, 2003.
[16] S.H. Lee, T.T.N. Doan, S.H. Ha, W.-J. Chang, Y.-M. Koo, "Influence of
ionic liquids as additives on sol-gel immobilized lipase", J. Mol. Cat. B:
Enzymatic., vol. 47, pp. 129-134, 2007.
[17] Y. Zhou, J.H. Schattka, M. Antonietti, "Room-temeperature ionic liquids
as template to monolythic mesoporous silica with wormlike pores via a
sol-gel nanocasting technique", Nano Lett., vol. 4, nr. 3, pp. 477-481,
2004.
[18] A. Ghanem, W. Schurig, "Lipase-catalyzed irreversible
transesterification of secondary alcohols using isopropenyl acetate",
Chem. Monthly, vol. 134, pp. 1151-1157, 2003.
[19] Z. Yang, W. Pan, "Ionic liquids: green solvnets for nonaqueous
biocatalysis", Enzyme Microb. Technol., vol. 37, pp.19-28, 2005.
[1] European Technology Platform on Sustainable Chemistry (2007, May)
Industrial or white biotechnology: a driver of sustainable growth in
Europe. Available: http://www.europabio.org/TPWhite/IB_Vision.pdf.
[2] M. Breuer, K. Ditrich, T. Habicher, B. Hauer, M. Kesseler, R. St├╝rmer,
T. Zelinski, ÔÇ×Industrial methods for the production of optically active
intermediates", Angew. Chem. Int. Ed., vol. 43, nr. 7, pp. 788-824, 2004.
[3] K. Buchholz, V. Kasche, U.T. Bornscheuer, Biocatalysts and enzyme
technology, Weinheim: Wiley-VCH Verlag, 2004, pp. 197-279.
[4] C. Mateo, J.M. Palomo, G. Fernandez-Lorente, J.M. Guisan, R.
Fernandez-Lafuente, "Improvement of enzyme activity, stability and
selectivity via immobilization techniques", Enzyme Microb. Technol.,
vol. 40, pp. 1451-1463, 2007.
[5] L. Cao, Carrier-bound immobilized enzymes: principles, applications
and design, Weinheim: Wiley-VCH, Verlag, 2005, pp. 16-36.
[6] R.A. Sheldon, "Enzyme immobilization: the quest for optimum
performance", Adv. Synth. Catal., vol 349, pp. 1289-1307, 2007.
[7] L. Betancor, H.R. Luckarift, "Bioinspired enzyme encapsulation for
biocatalysis", Trends Biotechnol., vol. 26, nr. 10, pp. 566-572, 2008.
[8] J. Livage, T. Coradin, C. Roux, ÔÇ×Encapsulation of biomolecules in silica
gels", J. Phys.: Condens. Matter, vol. 13, pp. 673-691, 2001.
[9] M.T. Reetz, P. Tielmann, W. Wiesenhöfer, W. Könen, A. Zonta,
ÔÇ×Second generation sol-gel encapsulated lipases: robust heterogeneous
biocatalysts", Adv. Synth. Catal., vol. 345, pp. 717-728, 2003.
[10] F. Peter, L. Poppe, C. Kiss, E. Szocs-Bir├│, G. Preda, C. Zarcula, A.
Olteanu, "Influence of precursors and additives on microbial lipases
stabilized by sol-gel entrapment", Biocat. Biotrans., vol. 23, nr. 3/4, pp.
251-260, 2005.
[11] A.C. Pierre, "The sol-gel encapsulation of biocatalysts", Biocat.
Biotrans., vol. 22, nr.3, pp. 145-170, 2004.
[12] S.H. Lee, T.T.N. Doan, S.H. Ha, W.-J Chang, Y.-M Koo, "Influence of
ionic liquids as additives on sol-gel immobilized lipase", J. Mol. Cat. B:
Enzymatic., vol. 47 pp. 129-134, 2007.
[13] C. Kiss, C. Zarcula, C. Csunderlik, F. Peter, "Enantioselective acylation
of secondary alcohols by biocatalysis with sol-gel immobilized
Pseudomonas fluorescens lipase, Rev. Chim. (Bucharest), vol. 58, nr. 8,
pp. 799-804, 2007.
[14] G. C.-S Chen. Y. Fujimoto, G. Girdauskas, C.J. Sih, "Quantitative
analyses of biochemical kinetic resolutions of enantiomers", J. Am.
Chem. Soc., vol. 104, pp. 7294-7299, 1982.
[15] F.Van Rantwijk, R.M. Lau, R.A. Sheldon, "Biocatalytic transformations
in ionic liquids", Trends Biotechnol., vol, 21, pp. 131-138, 2003.
[16] S.H. Lee, T.T.N. Doan, S.H. Ha, W.-J. Chang, Y.-M. Koo, "Influence of
ionic liquids as additives on sol-gel immobilized lipase", J. Mol. Cat. B:
Enzymatic., vol. 47, pp. 129-134, 2007.
[17] Y. Zhou, J.H. Schattka, M. Antonietti, "Room-temeperature ionic liquids
as template to monolythic mesoporous silica with wormlike pores via a
sol-gel nanocasting technique", Nano Lett., vol. 4, nr. 3, pp. 477-481,
2004.
[18] A. Ghanem, W. Schurig, "Lipase-catalyzed irreversible
transesterification of secondary alcohols using isopropenyl acetate",
Chem. Monthly, vol. 134, pp. 1151-1157, 2003.
[19] Z. Yang, W. Pan, "Ionic liquids: green solvnets for nonaqueous
biocatalysis", Enzyme Microb. Technol., vol. 37, pp.19-28, 2005.
@article{"International Journal of Chemical, Materials and Biomolecular Sciences:49925", author = "C. Zarcula and R. Croitoru and L. Corîci and C. Csunderlik and F. Peter", title = "Improvement of Lipase Catalytic Properties by Immobilization in Hybrid Matrices", abstract = "Lipases are enzymes particularly amenable for
immobilization by entrapment methods, as they can work equally
well in aqueous or non-conventional media and long-time stability of
enzyme activity and enantioselectivity is needed to elaborate more
efficient bioprocesses. The improvement of Pseudomonas
fluorescens (Amano AK) lipase characteristics was investigated by
optimizing the immobilization procedure in hybrid organic-inorganic
matrices using ionic liquids as additives. Ionic liquids containing a
more hydrophobic alkyl group in the cationic moiety are beneficial
for the activity of immobilized lipase. Silanes with alkyl- or aryl
nonhydrolizable groups used as precursors in combination with
tetramethoxysilane could generate composites with higher
enantioselectivity compared to the native enzyme in acylation
reactions of secondary alcohols. The optimal effect on both activity
and enantioselectivity was achieved for the composite made from
octyltrimethoxysilane and tetramethoxysilane at 1:1 molar ratio (60%
increase of total activity following immobilization and enantiomeric
ratio of 30). Ionic liquids also demonstrated valuable properties as
reaction media for the studied reactions, comparable with the usual
organic solvent, hexane.", keywords = "Ionic liquids, lipase, enantioselectivity, sol-gelimmobilization", volume = "3", number = "4", pages = "203-6", }