Studies of the chemoenzymatic modification of cellulosic pulps by the laccase-TEMPO system

Holzforschung

Volumn 65, Issue 4, 2011, Pages 475-481

  Patel, Ilabahen ^a   Ludwig, Roland ^a,b   Haltrich, Dietmar ^a   Rosenau, Thomas ^a   Potthast, Antje ^a  

^a UNIVERSITY OF NATURAL RESOURCES AND LIFE SCIENCES   (Austria)

^b RESEARCH CENTRE APPLIED BIOCATALYSIS   (Austria)

Author keywords

carbonyl content; carboxyl content; cellulose; gel permeation chromatography (GPC); laccase; laccase mediator system (LMS); TEMPO oxidation

Indexed keywords

CARBONYL CONTENT; CARBOXYL CONTENTS; GEL PERMEATION CHROMATOGRAPHY (GPC); LACCASE-MEDIATOR SYSTEM; LACCASES; TEMPO OXIDATION;

ALDEHYDES; CARBONYLATION; CELLULOSE; FUNCTIONAL GROUPS; GEL PERMEATION CHROMATOGRAPHY; IONS; METHANOL; SIZE EXCLUSION CHROMATOGRAPHY;

OXIDATION;

EID: 79959381412     PISSN: 00183830     EISSN: 1437434X     Source Type: Journal    
DOI: 10.1515/HF.2011.035     Document Type: Conference Paper

References (37)

1. Arends, I.W.C.E., Li, Y., Ausan, R., Sheldon, R.A. (2006a) Comparison of TEMPO and its derivatives as mediators in laccase catalysed oxidation of alcohols. Tetrahedron 62:6659-6665. (Pubitemid 43831944)
2. Arends, I.W.C.E., Li, Y.-X., Sheldon, R.A. (2006b) Stabilities and rates in the laccase/TEMPO-catalyzed oxidation of alcohols. Biocatal. Biotransform. 24:443-448. (Pubitemid 44921875)
3. Bohrn, R., Potthast, A., Schiehser, S., Rosenau, T., Sixta, H., Kosma, P. (2006) The FDAM method: determination of carboxyl profiles in cellulosic materials by combining group-selective fluorescence labeling with GPC. Biomacromolecules 7:1743-1750. (Pubitemid 43985093)
4. Bragd, P.L., van Bekkum, H., Besemer, A.C. (2004) TEMPO-mediated oxidation of polysaccharides: survey of methods and applications. Topics Catal. 27:49-66.
5. Cantarella, G., Galli, C., Gentili, P. (2004) Oxidation of non-phenolic substrates with the laccase/N-hydroxyacetanilide system: structure of the key intermediate from the mediator and mechanistic insight. New J. Chem. 28:366-372. (Pubitemid 38373023)
6. de Nooy, A.E.J., Bensemer, A.C., van Bekkum, H. (1995) Highly selective nitroxyl radical-mediated oxidation of primary alcohol groups in water-soluble glucans. Carbohydr. Res. 269:89-98.
7. de Nooy, A.E.J., Besemer, A.C., van Bekkum, H., van Dijk, J.A.P.P., Smit, J.A.M. (1996) TEMPO-mediated oxidation of pullulan and influence of ionic strength and linear charge density on the dimensions of the obtained polyelectrolyte chains. Macromolecules 29:6541-6547. (Pubitemid 126536624)
8. Fabbrini, M., Galli, C., Gentili, P., Macchitella, D. (2001) An oxidation of alcohols by oxygen with the enzyme laccase and mediation by TEMPO. Tetrahedron Lett. 42:7551-7553. (Pubitemid 32946953)
9. Fukuzumi, H., Saito, T., Iwata, T., Kumamoto, Y., Isogai, A. (2009) Transparent and high gas barrier films of cellulose nanofibers prepared by TEMPO-mediated oxidation. Biomacromolecules 10:162-165.
10. Galhaup, C., Goller, S., Peterbauer, C.K., Strass, J., Haltrich, D. (2002) Characterization of the major laccase isoenzyme from Trametes pubescens and regulation of its synthesis by metal ions. Microbiology SGM 148:2159-2169. (Pubitemid 34785299)
11. Goldstein, S., Merenyi, G., Russo, A., Samuni, A. (2003) The role of oxoammonium cation in the SOD-mimic activity of cyclic nitroxides. J. Am. Chem. Soc. 125:789-795. (Pubitemid 36109941)
12. 2 catalyzed by TEMPO and NaClO under acid-neutral conditions. Carbohydr. Polym. 78: 330-335.
13. Isogai, A., Kato, Y. (1998) Preparation of polyuronic acid from cellulose by TEMPO-mediated oxidation. Cellulose 5:153-164. (Pubitemid 128514301)
14. Isogai, T., Yanagisawa, M., Isogai, A. (2009) Degrees of polymerization (DP) and DP distribution of cellouronic acids prepared from alkali-treated celluloses and ball-milled native celluloses by TEMPO-mediated oxidation. Cellulose 16:117-127.
15. Isogai, T., Saito, T., Isogai, A. (2010) TEMPO electromediated oxidation of some polysaccharides including regenerated cellulose fiber. Biomacromolecules 11:1593-1599.
16. Marzorati, M., Danieli, B., Haltrich, D., Riva, S. (2005) Selective laccase-mediated oxidation of sugars derivatives. Green Chem. 7:310-315. (Pubitemid 40745560)
17. Mayer, A.M., Staples, R.C. (2002) Laccase: new functions for an old enzyme. Phytochemistry 60:551-565. (Pubitemid 34832184)
18. Patel, I., Ludwig, R., Mueangtoom, K., Haltrich, D., Rosenau, T., Potthast, A. (2009) Comparing soluble Trametes pubescens laccase and cross-linked enzymes crystals (CLECs) for enzymatic modification of cellulose. Holzforschung 63:715-720.
19. Potthast, A., Rosenau, T., Chen, C.L., Gratzl, J.S. (1996) A novel method for the conversion of benzyl alcohols to benzaldehydes by laccase-catalyzed oxidation. J. Mol. Catal. A: Chem. 108: 5-9. (Pubitemid 126654430)
20. Potthast, A., Röhrling, J., Rosenau, T., Borgards, A., Sixta, H., Kosma, P. (2003) A novel method for the determination of carbonyl groups in cellulosics by fluorescence labeling. 3. Monitoring oxidative processes. Biomacromolecules 4:743-749. (Pubitemid 36701247)
21. Potthast, A., Kostic, M., Schiehser, S., Kosma, P., Rosenau, T. (2007) Studies on oxidative modifications of cellulose in the periodate system - molecular weight distribution and carbonyl group profiles. Holzforschung 61:662-667. (Pubitemid 350059604)
22. Potthast, A., Schiehser, S., Rosenau, T., Kostic, M. (2009) Oxidative modification of cellulose in the periodate system - reduction and beta-elimination reactions. Holzforschung 63:12-17.
23. Röhrling, J., Potthast, A., Rosenau, T., Adorjan, I., Hofinger, A., Kosma, P. (2002) Synthesis of methyl β-D-glucopyranosides and methyl β-D-glucopyranosyl-(1→4)-β-D-glucopyranosides as substrates for fluorescence labeling reactions. Carbohydr. Res. 337:691-700. (Pubitemid 34304178)
24. Ruijssenaars, H.J., Hartmans, S. (2004) A cloned Bacillus halodurans multicopper oxidase exhibiting alkaline laccase activity. Appl. Microbiol. Biotechnol. 65:177-182. (Pubitemid 39062479)
25. Saito, T., Isogai, A. (2004) TEMPO-mediated oxidation of native cellulose. The effect of oxidation conditions on chemical and crystal structures of the water-insoluble fractions. Biomacro-molecules 5:1983-1989. (Pubitemid 39335240)
26. Saito, T., Isogai, A. (2006a) Introduction of aldehyde groups on surfaces of native cellulose fibers by TEMPO-mediated oxidation. Coll. Surf. A: Physicochem. Eng. Aspects 289:219-225. (Pubitemid 44441893)
27. Saito, T., Isogai, A. (2006b) Introduction of aldehyde groups on surfaces of native cellulose fibers by TEMPO-mediated oxidation. Coll. Surf. A: Physicochem. Eng. Aspects 289:219-225. (Pubitemid 44441893)
28. Saito, T., Nishiyama, Y., Putaux, J.-L., Vignon, M., Isogai, A. (2006c) Homogeneous suspensions of individualized microfibrils from TEMPO-catalyzed oxidation of native cellulose. Biomacromolecules 7:1687-1691. (Pubitemid 43985084)
29. Sheldon, R.A., Arends, I.W.C.E. (2004) Organocatalytic oxidations mediated by nitroxyl radicals. Adv. Synth. Catal. 346: 1051-1071. (Pubitemid 39345664)
30. Shibata, I., Isogai, A. (2003a) Depolymerization of cellouronic acid during TEMPO-mediated oxidation. Cellulose 10:151-158. (Pubitemid 36861749)
31. Shibata, I., Isogai, A. (2003b) Nitroxide-mediated oxidation of cellulose using TEMPO derivates: HPSEC and NMR analyses of the oxidized products. Cellulose 10:335-341. (Pubitemid 37529416)
32. Shibata, I., Yanagisawa, M., Saito, T., Isogai, A. (2006) SEC-MALS analysis of cellouronic acid prepared from regenerated cellulose by TEMPO-mediated oxidation. Cellulose 13:73-80.
33. Shleev, S., Wang, Y., Gorbacheva, M., Christenson, A., Haltrich, D., Ludwig, R., Ruzgas, T., Gorton, L. (2008) Direct heterogeneous electron transfer reactions of Bacillus halodurans bacterial blue multicopper oxidase. Electroanalysis 20:963-969.
34. 2 under acid conditions. Carbohydr. Polym. 81: 592-598.
35. Viikari, L., Kruus, K., Buchert, J. (1999) Method for modification of cellulose WO/1999/23117 (PCT/FI1999/000861). Valtion Teknillinen Tutkimuskeskus, Finland.
36. Wells, A., Teria, M., Eve, T. (2006) Green oxidations with laccase-mediator systems. Biochem. Soc. Trans. 34:304-308.
37. 13C NMR and deuterium isotope effects on tautomeric equilibria. J. Org. Chem. 66:6244-6251. (Pubitemid 32868355)