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International Journal of the Biology, Chemistry, Physics, and Technology of Wood

Editor-in-Chief: Faix, Oskar

Editorial Board Member: Daniel, Geoffrey / Militz, Holger / Rosenau, Thomas / Salmen, Lennart / Sixta, Herbert / Vuorinen, Tapani / Argyropoulos, Dimitris S. / Balakshin, Yu / Barnett, J. R. / Berry, Richard / Burgert, Ingo / Evans, Robert / Evtuguin, Dmitry V. / Frazier, Charles E. / Fukushima, Kazuhiko / Gellerstedt, Göran / Gindl-Altmutter, Wolfgang / Glasser, W. G. / Heitner, Cyril / Holmbom, Bjarne / Isogai, Akira / Kadla, John F. / Kleen, Marjatta / Koch, Gerald / Lachenal, Dominique / Mansfield, Shawn D. / Morrell, J.J. / Niemz, Peter / Pizzi, Antonio / Ragauskas, Arthur J. / Ralph, John / Rice, Robert W. / Salin, Jarl-Gunnar / Schmitt, Uwe / Schultz, Tor P. / Schwanninger, Manfred / Sipilä, Jussi / Tamminen, Tarja / Viikari, Liisa / Welling, Johannes / Willför, Stefan / Yoshihara, Hiroshi

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Studies on the dehydrogenative polymerization of monolignol β-glycosides. Part 6: Monitoring of horseradish peroxidase-catalyzed polymerization of monolignol glycosides by GPC-PDA

Yuki Tobimatsu1, 2 / Toshiyuki Takano1 / Hiroshi Kamitakahara1 / Fumiaki Nakatsubo3

1Division of Forest and Biomaterials Science, Graduate School of Agriculture, Kyoto University, Kyoto, Japan

2Department of Biochemistry, University of Wisconsin-Madison, Madison, WI, USA

3Research Institute for Sustainable Humanosphere, Kyoto University, Kyoto, Japan

Corresponding author. Division of Forest and Biomaterials Science, Graduate School of Agriculture, Kyoto University, Kitashirakawa-oiwakecho Sakyo-ku, Kyoto, 606-8502, Japan Phone: +81-75-753-6255 Fax: +81-75-753-6300

Citation Information: Holzforschung. Volume 64, Issue 2, Pages 173–181, ISSN (Online) 1437-434X, ISSN (Print) 0018-3830, DOI: 10.1515/hf.2010.026, January 2010

Publication History

Published Online:


Horseradish peroxidase (HRP)-catalyzed dehydrogenative polymerization of guaiacyl (G) and syringyl (S)-type monolignol γ-O-glucosides, isoconiferin (iso-G) and isosyringin (iso-S), which contain a hydrophilic glucosyl unit on γ-position of coniferyl alcohol and sinapyl alcohol, respectively, was monitored by gel permeation chromatography coupled with photodiode array detection (GPC-PDA). Contrary to the conventional dehydrogenative polymerization of monolignols, the polymerization of the glycosides produces water-soluble synthetic lignins (DHPs) in a homogeneous aqueous phase. Taking advantage of this unique reaction system, the method was developed to follow the changes of molecular weights in the course of DHP formations. Moreover, PDA detection permits determination of oligomeric S-type quinone methide intermediates (QMs) formed as stable transient compounds during polymerization of iso-S. A detailed comparison of the polymerization profiles revealed entirely different behaviors of G- and S-type monomers. The data strongly support the view that the low reactivity of oligomeric S-type QMs impedes the formation of DHPs from S-type monomers. In copolymerization of G- and S-type monomers, it is conceivable that G-type phenolic hydroxyl groups serve as good nucleophilic reactants to scavenge S-type QMs resulting in efficient production of DHPs. As a consequence, the present approach can be a powerful tool to study the in vitro dehydrogenative polymerization providing further mechanistic insights into lignin polymerization in vivo.

Keywords: dehydrogenation polymer (DHP); dehydrogenative polymerization; gel permeation chromatography (GPC); horseradish peroxidase (HRP); lignin biosynthesis; monolignol β-d-glucoside; photodiode array (PDA) detection; quinone methide (QM); syringyl lignin

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