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Laccase-catalysed functionalisation of TMP with tyramine

  • Stina Grönqvist , Kari Rantanen , Raimo Alén , Maija-Liisa Mattinen , Johanna Buchert and Liisa Viikari
Published/Copyright: August 16, 2006
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Holzforschung
From the journal Volume 60 Issue 5

Abstract

Modified wood fibres open new perspectives to create value-added products based on renewable raw materials. An interesting option is the targeted modification of fibre surfaces by oxidative enzymes. This two-stage functionalisation method consists of enzymatic activation of fibre surfaces followed by addition of radicalised compounds reacting preferentially by radical coupling. In this work, the activation of bleached and unbleached softwood TMPs with laccase isolated from Trametes hirsuta was studied. The formation and stability of the radicals were studied by EPR spectroscopy. The reaction of the radicals with 3-hydroxytyramine hydrochloride and the type of chemical linkages were investigated. EPR, ESCA and FTIR spectroscopy were used for analysis. Bleached TMP was radicalised more efficiently than unbleached TMP. The radicals were unstable, as 90% of them were quenched within a few hours. Their lifetime was, however, found to be adequately long for performing coupling reactions. Bonding of new compounds to pulps via radical reactions thus seems to be possible.

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Corresponding author. VTT Technical Research Centre of Finland, P.O. Box 1000, FI-02044 VTT, Espoo, Finland

References

Alén, R. (2000) Structure and chemical composition of wood. In: Forest Products Chemistry. Ed. Stenius, P. Fapet Oy, Jyväskylä. pp. 12–57.Search in Google Scholar

Brunow, G., Kilpeläinen, I., Sipilä, J., Syrjänen, K., Karhunen, P., Setälä, H., Rummakko, P. (1998) Oxidative coupling of phenols and the biosynthesis of lignin. In: Lignin and Lignan Biosythesis, ACS Symposium Series Vol. 697. Eds. Lewis, N., Sarkanen, S. American Chemical Society, Washington, DC. pp. 131–147.10.1021/bk-1998-0697.ch010Search in Google Scholar

Buchert, J., Mustranta, A., Tamminen, T., Spetz, P., Holmbom, B. (2002) Modification of spruce lignans with Trametes hirsuta laccase. Holzforschung56:579–584.10.1515/HF.2002.088Search in Google Scholar

Chandra, R., Ragauskas, A. (2001) Sculpting the molecular weight of lignin via laccase. In: Proceedings of the 11th International Symposium on Wood and Pulp Chemistry, Nice, France, 2001, Part II. pp. 39–42.Search in Google Scholar

Chandra, R., Ragauskas, A. (2002a) Fibre modification with laccase: you say you want a revolution. In: Abstracts of the 223rd ACS National Meeting, book 1. American Chemical Society, Washington, DC. p. 104.Search in Google Scholar

Chandra, R., Ragauskas, A. (2002b) Evaluating laccase-catalysed coupling of phenolic acids to high-yield kraft pulps. Enzyme Microb. Technol.30:855–861.10.1016/S0141-0229(02)00020-0Search in Google Scholar

Chandra, R., Lehtonen, L., Ragauskas, A. (2004a) Modification of high lignin content kraft pulps with laccase to improve paper strength properties. 1. Laccase treatment in the presence of gallic acid. Biotechnol. Prog.20:255–261.10.1021/bp0300366Search in Google Scholar

Chandra, R., Felby, C., Ragauskas, A. (2004b) Improving laccase-facilitated grafting of 4-hydroxybenzoic acid to high-kappa pulps. J. Wood Chem. Technol.24:69–81.10.1081/WCT-120035945Search in Google Scholar

Felby, C., Pedersen, L.S., Nielsen, B.R. (1997a) Enhanced auto adhesion of wood fibres using phenol oxidases. Holzforschung51:281–286.10.1515/hfsg.1997.51.3.281Search in Google Scholar

Felby, C., Nielsen, B.R., Olesen, P.O., Skibsted, L.H. (1997b) Identification and quantification of radical reaction intermediates by electron spin resonance spectrometry of laccase-catalysed oxidation of wood fibres from beech (Fagus sylvatica). Appl. Microbiol. Biotechnol.48:459–464.10.1007/s002530051080Search in Google Scholar

Felby, C., Hassinboe, J., Lund, M. (2002) Pilot-scale production of fibreboards made by laccase oxidised wood fibres: board properties and evidence for crosslinking of lignin. Enzyme Microb. Technol.31:736–741.10.1016/S0141-0229(02)00111-4Search in Google Scholar

Gajhede, M. (2001) Horseradish peroxidase. In: Handbook of Metalloproteins. Eds. Messerchmidt, A., Huber, R., Poulos, T., Wieghardt, K. John Wiley & Sons, Chichester. pp. 195–210.Search in Google Scholar

Gianfreda, L., Xu, F., Bollag, J.M. (1999) Laccases: A useful group of oxidoreductive enzymes. Bioremediation J.31:1–25.10.1080/10889869991219163Search in Google Scholar

Grönqvist, S., Suurnäkki, A., Niku-Paavola, M.-L., Kruus, K., Buchert, J., Viikari, L. (2003a) Lignocellulose processing with oxidative enzymes. In: Applications of Enzymes to Lignocellulosics, ACS Symposium Series, Vol. 855. Eds. Mansfield, S.D., Saddler, J.N. American Chemical Society, Washington, DC. pp. 46–65.10.1021/bk-2003-0855.ch003Search in Google Scholar

Grönqvist, S., Buchert, J., Rantanen, K., Viikari, L., Suurnäkki, A. (2003b) Activity of laccase on unbleached and bleached thermomechanical pulp. Enzyme Microb. Technol.32:439–445.10.1016/S0141-0229(02)00319-8Search in Google Scholar

Grönqvist, S., Viikari, L., Niku-Paavola, M.-L., Orlandi, M., Canevali, C., Buchert, J. (2005) Oxidation of milled wood lignin with laccase, tyrosinase and horseradish peroxidase. Appl. Microbiol. Biotechnol.67:489–494.10.1007/s00253-004-1800-6Search in Google Scholar PubMed

Huttermann, A., Mai, C., Kharazipour, A. (2001) Modification of lignin for the production of new compounded materials. Appl. Microbiol. Biotechnol.55:387–395.10.1007/s002530000590Search in Google Scholar PubMed

Johansson, L.-S., Campbell, J., Koljonen, K., Kleen, M., Buchert, J. (2004) On surface distributions in natural cellulosic fibres. Surf. Interface Anal.36:706–710.10.1002/sia.1741Search in Google Scholar

Kirk, T.K., Cullen, D. (1998) Enzymology and molecular genetics of wood degradation by white-rot fungi. In: Environmentally Friendly Technologies for the Pulp and Paper Industry. Eds. Young, R.A., Akhtar, M. John Wiley & Sons, New York. pp. 273–307.Search in Google Scholar

Kirk, T., Farrell, R. (1987) Enzymatic “combustion”: The microbial degradation of lignin, Annu. Rev. Microbiol.41:465–505.10.1146/annurev.mi.41.100187.002341Search in Google Scholar PubMed

Lund, M., Felby, C., Bjerrum, M. (1998) Modification of kraft pulp and lignin by co-polymerisation of phenolic compounds initiated by laccase. In: Proceedings of the 7th International Conference on Biotechnology in the Pulp and Paper Industry, Vol. C, Vancouver. pp. C139–C142.Search in Google Scholar

Niku-Paavola, M.-L., Karhunen, E., Salola, P., Raunio, V. (1998) Lignolytic enzymes of the white-rot fungus Phlebia radiata. Biochem. J.254:877–884.Search in Google Scholar

Poppius-Levlin, K., Whang, W., Tamminen, T., Hortling, B., Viikari, L., Niku-Paavola, M.-L. (1999) Effects of laccase/HBT treatment on pulp and lignin structures. J. Pulp Pap. Sci.3:90–94.Search in Google Scholar

Sjöström, E. Wood Chemistry, Fundamentals and Applications, 2nd edition. Academic Press, New York, 1993.Search in Google Scholar

Thurston, C.F. (1994) The structure and function of fungal laccases. Microbiology140:19–26.10.1099/13500872-140-1-19Search in Google Scholar

Widsten, P., Laine, J.E., Tuominen, S. (2002) Radical formation on laccase treatment of softwoods defibrated at high temperatures. II. Studies with softwood fibres. Cellulose Chem. Technol.36:161–172.Search in Google Scholar

Published Online: 2006-08-16
Published in Print: 2006-08-01

©2006 by Walter de Gruyter Berlin New York

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