Abstract
The selective oxidation of hydrocarbons is an important value-enhancing chemical transformation in particular with respect to fine chemicals and pharmaceuticals production. Enzymatic oxidations operate under mild reaction conditions and produce little if any waste. However, its industrial use is still limited mainly due to their high cost and the low space time yields. In the present work, chloroperoxiase from Calariomyces fumago immobilized on the mesoporous molecular sieve SBA-15 was applied for the oxidation of indole to 2-oxoindole using hydrogen peroxide or tert.-butyl hydroperoxide as oxidants. The performance of the immobilized enzyme was found to be superior to native chloroperoxidase with respect to maximum conversion and pH range applicable. However, immobilized CPO is still sensitive to high concentrations of hydrogen peroxide. The use of tert.-buty hydroperoxide is found to avoid this problem, but the reaction rate is significantly reduced.
Similar content being viewed by others
References
D.R. Morris and L.P. Hager, J. Biol. Chem. 241, 1763 (1966).
M.P.J. van Deurzen, F. van Rantwijk, and R.A. Sheldon, Tetrahedron 53, 13183 (1997).
S. Colonna, N. Gaggero, C. Richelmi, and P. Pasta, Trends Biotechnol. 17, 163 (1999).
W. Adam, M. Lazarus, C.R. Saha-Möller, O. Weichold, U. Hoch, D. Häring, and P. Schreier, Adv. Biochem. Eng. Biotechnol. 63, 73 (1999).
F. van Rantwijk and R.A. Sheldon, Curr. Opin. Biotechnol. 11, 554 (2000).
R. Vazquez-Duhalt, M. Ayala, and F.J. Marquez-Rocha, Phytochemistry 58, 929 (2001).
S. Colonna, N. Gaggero, L. Casella, G. Carrera, and P. Pasta, Tetrahedron Asymmetry 3, 95 (1992).
L.P. Hager, F.J. Lakner, and A. Basavapathruni, J. Mol. Catal. B: Enzym. 5, 95 (1998).
M.D. Corbett and B.R. Chipko, Biochem. J. 183, 269 (1979).
T.A. Kadima and M.A. Pickard, Appl. Environ. Microbiol. 56, 3474 (1990).
S. Aoun and M. Baboulene, J. Mol. Catal. B: Enzym. 4, 101 (1998).
Y.J. Han, J.T. Watson, G. D. Stucky, and A. Butler, J. Mol. Catal. B: Enzym. 17, 1 (2002).
M. Bakker, F. van de Velde, F. van Ranwijk, and R.A. Sheldon, Biotechnol. Bioeng. 70, 342 (2000).
A. Petri, T. Gambicorti, and P. Salvadori, J. Mol. Catal. B: Enzym. 27, 103 (2004).
A. Borole, S. Dai, C.L. Cheng, M. Rodriguez, and B.H. Davison, Appl. Biochem. Biotechnol. 273, 113 (2004).
V. Trevisan, M. Signoretto, S. Colonna, V. Pironti, and G., Strukul, Angew, Chem. Int. Ed. 43, 4097 (2004).
M. Hartmann and A. Vinu, Langmuir 18, 8010 (2002).
D.Y. Zhao, Q.S. Huo, J.L. Feng, B.F. Chmelka, and G.D. Stucky, J. Am. Chem. Soc. 120, 6024 (1998).
D.Y. Zhao, J.L. Feng, Q.S. Huo, N. Melosh, G.H. Fredrickson, B.F. Chmelka, and G.D. Stucky, Science 279, 548 (1998).
K.S.W. Sing, D.H. Everett, R.A.W. Haul, L. Moscow, R.A. Pierotti, J. Rouquérol, and T. Siemieniewska, Pure Appl. Chem. 57, 603 (1985).
M. Imperor-Clerc, P. Davidson, and A. Davidson, J. Am. Chem. Soc. 122, 11925 (2000).
P. Selvam, S.K. Bhatia, and C.G. Sonwane, Ind. Eng. Chem. Res. 40, 3237 (2001).
E. Torres, B. Siminovich, E. Barzana, and R. Vazquez-Duhalt, J. Mol. Catal. B: Enzym. 4, 155 (1998).
F. van de Velde, M. Bakker, F. van Rantwijk, and R.A. Sheldon, Biotechnol. Bioeng. 72, 523 (2001).
L. Santhanam and J.S. Dordick, Biocatal. Biotransform. 20, 265 (2002).
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Hartmann, M., Streb, C. Selective oxidation of indole by chloroperoxidase immobilized on the mesoporous molecular sieve SBA-15. J Porous Mater 13, 347–352 (2006). https://doi.org/10.1007/s10934-006-8029-y
Issue Date:
DOI: https://doi.org/10.1007/s10934-006-8029-y