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Wood Research and Technology


Cellulose – Hemicelluloses – Lignin – Wood Extractives

Editor-in-Chief: Salmén, Lennart

Editorial Board: Daniel, Geoffrey / Militz, Holger / Rosenau, Thomas / Sixta, Herbert / Vuorinen, Tapani / Argyropoulos, Dimitris S. / Balakshin, Yu / Barnett, J. R. / Burgert, Ingo / Rio, Jose C. / Evans, Robert / Evtuguin, Dmitry V. / Frazier, Charles E. / Fukushima, Kazuhiko / Gindl-Altmutter, Wolfgang / Glasser, W. G. / Holmbom, Bjarne / Isogai, Akira / Kadla, John F. / Koch, Gerald / Lachenal, Dominique / Laine, Christiane / Mansfield, Shawn D. / Morrell, J.J. / Niemz, Peter / Potthast, Antje / Ragauskas, Arthur J. / Ralph, John / Rice, Robert W. / Salin, Jarl-Gunnar / Schmitt, Uwe / Schultz, Tor P. / Sipilä, Jussi / Takano, Toshiyuki / Tamminen, Tarja / Theliander, Hans / Welling, Johannes / Willför, Stefan / Yoshihara, Hiroshi

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Volume 73, Issue 2


Radical transfer system in the enzymatic dehydrogenative polymerization (DHP formation) of coniferyl alcohol (CA) and three dilignols

Yasuyuki Matsushita
  • Corresponding author
  • Graduate School of Bioagricultural Sciences, Nagoya University, Nagoya 464-8601, Japan, Phone/Fax: +81-52-789-4174
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/ Masaya Okayama / Dan Aoki / Sachie Yagami / Kazuhiko Fukushima
Published Online: 2018-08-13 | DOI: https://doi.org/10.1515/hf-2018-0044


No clear picture has yet been elaborated concerning the mechanism of lignin growth, and thus this topic is the focus of the present paper. Namely, the enzymatic dehydrogenative polymerization (DHP formation) of coniferyl alcohol (CA, as a monolignol) and three dilignols and their reaction kinetics were investigated. The dilignols [guaiacylglycerol-β-coniferyl ether (IβO4), dehydrodiconiferyl alcohol (IIβ5), and pinoresinol (IIIββ)] and CA as a monolignol [(3-OCD3)-coniferyl alcohol (CAOCD3)] were synthesized and subjected to enzymatic DHP formation. The dilignol derived from CAOCD3 could be identified by its higher molecular weight in comparison with the starting dilignols (IβO4, IIβ5, and IIIββ). Based on the observed consumption rate of the CA and its dilignols, it was proposed that a radical transfer system exists between the dilignols, which is generated from the CA and the starting substrates.

Keywords: coniferyl alcohol; dehydrodiconiferyl alcohol; dilignol; enzymatic dehydrogenative polymerization; guaiacylglycerol-β-coniferyl ether; monolignol; pinoresinol; radical transfer


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About the article

Received: 2018-03-06

Accepted: 2018-07-18

Published Online: 2018-08-13

Published in Print: 2019-02-25

Author contributions: All the authors have accepted responsibility for the entire content of this submitted manuscript and approved submission.

Research funding: None declared.

Employment or leadership: None declared.

Honorarium: None declared.

Citation Information: Holzforschung, Volume 73, Issue 2, Pages 189–195, ISSN (Online) 1437-434X, ISSN (Print) 0018-3830, DOI: https://doi.org/10.1515/hf-2018-0044.

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