Studies on the dehydrogenative polymerization of monolignol β-glycosides: Part 5. UV spectroscopic monitoring of horseradish peroxidase-catalyzed polymerization of monolignol glycosides

Holzforschung

Volumn 62, Issue 5, 2008, Pages 501-507

  Tobimatsu, Yuki ^a   Takano, Toshiyuki ^a   Kamitakahara, Hiroshi ^a   Nakatsubo, Fumiaki ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

Copolymerization; Dehydrogenation polymer (DHP); Dehydrogenative polymerization; Horseradish peroxidase (HRP); Lignin; Monolignol D glucoside; Quinone methide; UV spectroscopy

Indexed keywords

CARBOHYDRATES; CHEMICAL REACTIONS; HOMOPOLYMERIZATION; MONOMERS; POLYMERIZATION; SUGARS; ULTRAVIOLET SPECTROSCOPY;

ABSORBANCE BANDS; AQUEOUS PHASE; CATALYZED POLYMERIZATION; COPOLYMERIZATION; DEHYDROGENATION POLYMER; DEHYDROGENATION POLYMER (DHP); DEHYDROGENATIVE POLYMERIZATION; GUAIACYL; HORSE RADISH PEROXIDASE; HORSERADISH PEROXIDASE (HRP); LIGNIN; LIGNIN POLYMERS; QUINONE METHIDE; SPECTROSCOPIC MONITORING; UV SPECTROSCOPY;

POLYMERS;

ARMORACIA RUSTICANA;

EID: 48649101951     PISSN: 00183830     EISSN: 1437434X     Source Type: Journal    
DOI: 10.1515/HF.2008.094     Document Type: Article

References (40)

1. 13C labelled coniferyl alcohol to detect "end-wise" polymerization in the formation of DHPs. Holzforschung 54:604-608.
2. Aoyama, W., Sasaki, S., Matsumura, S., Mitsunaga, T., Hirai, H., Tsutsumi, Y., Nishida, T. (2002) Sinapyl alcohol-specific peroxidase isoenzyme catalyzes the formation of the dehydrogenative polymer from sinapyl alcohol. J. Wood Sci. 48: 497-504.
3. Boerjan, W., Ralph, J., Baucher, M. (2003) Lignin biosynthesis. Annu. Rev. Plant. Biol. 54:519-546.
4. Brunow, G., Sipila, J., Makela, T. (1989) On the mechanism of formation of noncyclic benzyl ethers during lignin biosynthesis. Part 1. The reactivity of β-O-4-quinone methides with phenols and alcohols. Holzforschung 43:55-59.
5. Brunow, G., Karlsson, O., Lundquist, K., Sipila, J. (1993) On the distribution of the diastereomers of the structural elements in lignins: the steric course of reactions mimicking lignin biosynthesis. Wood Sci. Technol. 27:281-286.
6. Capanema, E.A., Balakshin, M.Y., Kadla, J.F. (2004) A comprehensive approach for quantitative lignin characterization by NMR spectroscopy. J. Agric. Food Chem. 52:1850-1860.
7. 31P and 2D NMR spectroscopy. The occurrence of ester bonds and α-O-4 substructures. J. Agric. Food Chem. 45:1212-1219.
8. Faix, O., Besold, G. (1978) Characterisation of dehydrogenation polymers prepared from p-hydroxy-cinnamic alcohols (DHPs) with special focus on polymerisates composed only of 4-hydrox-phenyl- or guaiacyl- or syringyl-propane units. Holzforschung 32:1-7 (in German).
9. Fournand, D., Cathala, B., Lapierre, C. (2003) Initial steps of the peroxidase-catalyzed polymerization of coniferyl alcohol and/or sinapyl aldehyde capillary zone electrophoresis study of pH effect. Phytochemistry 62:139-146.
10. Freudenberg, K., Hübner, H.H. (1952) Hydroxycinnamyl alcohols and their dehydrogenation polymers. Chem. Ber. 85:1181-1191.
11. Grabber, J.H. (2005) How do lignin composition, structure, and cross-linking affect degradability? A review of cell wall model studies. Crop Sci. 45:820-831.
12. 2 as the oxidant. J. Wood Sci. 51:607-614.
13. 13C-NMR characterization of guaiacyl, guaiacyl/syringyl, and syringyl dehydrogenation polymers. Holzforschung 52:160-170.
14. Lu, F., Ralph, J. (2002) Preliminary evidence for sinapyl acetate as a lignin monomer in kenaf. Chem. Commun. 90-91.
15. Lu, F., Ralph, J., Morreel, K., Messens, E., Boerjan, W. (2004) Preparation and relevance of a cross-coupling product between sinapyl alcohol and sinapyl p-hydroxybenzoate. Org. Biomol. Chem. 2:2888-2890.
16. Nakatsubo, F., Sato, K., Higuchi, T. (1975) Synthesis of guaiacylglycerol-β-guaiacyl ether. Holzforschung 29:165-168.
17. Nakatsubo, F., Sato, K., Higuchi, T. (1976) Enzymic dehydrogenation of p-coumaryl alcohol. IV. Reactivity of quinonemethide. Mokuzai Gakkaishi 22:29-33.
18. Pew, J.C., Connors, W.J., Kunishi, A. (1964) Enzymic dehydrogenation of lignin model phenols. In: Actes du Symposium International Chimie et Biochimie de la Lignine, de la Cellulose et des Hemicelluloses, Grenoble, France. pp. 229-245.
19. Quideau, S., Ralph, J. (1992) Facile large-scale synthesis of coniferyl, sinapyl, and p-coumaryl alcohol. J. Agric. Food Chem. 40:1108-1110.
20. a-values of guaiacyl and syringyl phenols related to lignin. J. Wood Chem. Technol. 20:277-305.
21. Ralph, J., Young, R.A. (1983) Stereochemical aspects of addition reactions involving lignin model quinone methides. J. Wood Chem. Technol. 3:161-181.
22. Ralph, J., Lundquist, K., Brunow, G., Lu, F., Kim, H., Schatz, P.F., Marita, J.M., Hatfield, R.D., Ralph, S.A., Christensen, J.H., Boerjan, W. (2004) Lignins: Natural polymers from oxidative coupling of 4-hydroxyphenylpropanoids. Phytochem. Rev. 3:29-60.
23. 31P NMR spectroscopy. Phytochemistry 43:499-507.
24. Sasaki, S., Nishida, T., Tsutsumi, Y., Kondo, R. (2004) Lignin dehydrogenative polymerization mechanism: a poplar cell wall peroxidase directly oxidizes polymer lignin and produces in vitro dehydrogenative polymer rich in β-O-4 linkage. FEBS Lett. 562:197-201.
25. Schweers, W., Faix, O. (1973) Polymer models of lignins (DHPs) of different composition. I. Preparation of polymer models of lignins with different ratios of the three monolignols p-coumaryl alcohol, coniferyl alcohol, and sinapyl alcohol. Holzforschung 27:208-213 (in German).
26. Sipilä, J., Brunow, G. (1991) On the mechanism of formation of non-cyclic benzyl ethers during lignin biosynthesis. Part 2. The effect of pH on the reaction between a β-O-4-type quinone methide and vanillyl alcohol in water-dioxane solutions. The stability of non-cyclic benzyl aryl ethers during lignin biosynthesis. Holzforschung 45:275-278.
27. Sipilä, J., Brunow, G. (1992) Quinone methide reactivity as a tool in investigating lignin biosynthesis. Bull. Liaison-Groupe Polyphenols 16:140-143.
28. 13C NMR spectroscopic characterisation of six dimeric arylglycerol-β-aryl ether model compounds representative of syringyl and p-hydroxyphenyl structures in lignins. On the aldol reaction in β-ether preparation. Holzforschung 49:325-331.
29. Sterjiades, R., Dean, J.F.D., Gamble, G., Himmelsbach, D.S., Eriksson, K.E.L. (1993) Extracellular laccases and peroxidases from sycamore maple (Acer pseudoplatanus) cell-suspension cultures. Reactions with monolignols and lignin model compounds. Planta 190:75-87.
30. Takahama, U., Oniki, T., Shimokawa, H. (1996) A possible mechanism for the oxidation of sinapyl alcohol by peroxidase-dependent reactions in the apoplast: enhancement of the oxidation by hydroxycinnamic acids and components of the apoplast. Plant Cell Physiol. 37:499-504.
31. Takano, T., Tobimatsu, Y., Hosoya, T., Hattori, T., Ohnishi, J., Takano, M., Kamitakahara, H., Nakatsubo, F. (2006) Studies on the dehydrogenative polymerizations of monolignol β-glycosides. Part 1. Syntheses of monolignol b-glycosides, (E)-isoconiferin, (E)-isosyringin, and (E)-triandrin. J. Wood Chem. Technol. 26:215-229.
32. Tanahashi, M., Higuchi, T. (1990) Effect of the hydrophobic regions of hemicelluloses on dehydrogenative polymerization of sinapyl alcohol. Mokuzai Gakkaishi 36:424-428.
33. Tanahashi, M., Takeuchi, H., Higuchi, T. (1976) Dehydrogenative polymerization of 3,5-substituted p-coumaryl alcohols. Wood Res. 61:44-53.
34. Tobimatsu, Y., Takano, T., Kamitakahara, H., Nakatsubo, F. (2006) Studies on the dehydrogenative polymerizations of monolignol β-glycosides. Part 2: Horseradish peroxidase-catalyzed dehydrogenative polymerization of isoconiferin. Holzforschung 60:513-518.
35. Tobimatsu, Y., Takano, T., Kamitakahara, H., Nakatsubo, F. (2008a) Azide ion as a quinone methide scavenger in the horseradish peroxidase-catalyzed polymerization of sinapyl alcohol. J. Wood Sci. 54:87-89.
36. Tobimatsu, Y., Takano, T., Kamitakahara, H., Nakatsubo, F. (2008b) Studies on the dehydrogenative polymerizations of monolignol β-glycosides. Part 3. Horseradish peroxidase-catalyzed polymerizations of triandrin and isosyringin. J. Wood Chem. Technol., in press.
37. Tobimatsu, Y., Takano, T., Kamitakahara, H., Nakatsubo, F. (2008c) Studies on dehydrogenative polymerizations of monolignol β-glycosides. Part 4. Horseradish peroxidase-catalyzed copolymerization of isoconiferin and isosyringin. Holzforschung, in press.
38. Yamasaki, T., Hata, K., Higuchi, T. (1976) Dehydrogenation polymer of sinapyl alcohol by peroxidase and hydrogen peroxide. Mokuzai Gakkaishi 22:582-588.
39. Yoshida, S., Chatani, A., Tanahashi, M., Honda, Y., Watanabe, T., Kuwahara, M. (1998) Preparation of synthetic lignin by manganese peroxidase of Bjerkandera adusta in organic solvents. Holzforschung 52:282-286.
40. Weymouth, N., Dean, J.F.D., Eriksson, K.E.L., Morrison, W.H. III, Himmelsbach, D.S., Hartley, R.D. (1993) Synthesis and spectroscopic characterization of p-hydroxyphenyl, guaiacyl and syringyl lignin polymer models (DHPs). Nordic Pulp Paper Res. J. 8:344-349, 383.