Jump to ContentJump to Main Navigation
Show Summary Details
More options …

Holzforschung

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. / 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

12 Issues per year


IMPACT FACTOR 2016: 1.868
5-year IMPACT FACTOR: 1.875

CiteScore 2016: 1.83

SCImago Journal Rank (SJR) 2015: 0.817
Source Normalized Impact per Paper (SNIP) 2015: 0.954

Online
ISSN
1437-434X
See all formats and pricing
More options …
Volume 64, Issue 2 (Feb 2010)

Issues

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

Yuki Tobimatsu
  • Division of Forest and Biomaterials Science, Graduate School of Agriculture, Kyoto University, Kyoto, Japan
  • Department of Biochemistry, University of Wisconsin-Madison, Madison, WI, USA
  • Other articles by this author:
  • De Gruyter OnlineGoogle Scholar
/ Toshiyuki Takano
  • Division of Forest and Biomaterials Science, Graduate School of Agriculture, Kyoto University, Kyoto, Japan
  • Other articles by this author:
  • De Gruyter OnlineGoogle Scholar
/ Hiroshi Kamitakahara
  • Division of Forest and Biomaterials Science, Graduate School of Agriculture, Kyoto University, Kyoto, Japan
  • Other articles by this author:
  • De Gruyter OnlineGoogle Scholar
/ Fumiaki Nakatsubo
Published Online: 2010-01-14 | DOI: https://doi.org/10.1515/hf.2010.026

Abstract

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

About the article

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


Received: 2009-08-20

Accepted: 2009-09-09

Published Online: 2010-01-14

Published Online: 2010-01-14

Published in Print: 2010-02-01


Citation Information: Holzforschung, ISSN (Online) 1437-434X, ISSN (Print) 0018-3830, DOI: https://doi.org/10.1515/hf.2010.026.

Export Citation

Citing Articles

Here you can find all Crossref-listed publications in which this article is cited. If you would like to receive automatic email messages as soon as this article is cited in other publications, simply activate the “Citation Alert” on the top of this page.

[1]
Yuki Tobimatsu, Armin Wagner, Lloyd Donaldson, Prajakta Mitra, Claudiu Niculaes, Oana Dima, Jeong Im Kim, Nickolas Anderson, Dominique Loque, Wout Boerjan, Clint Chapple, and John Ralph
The Plant Journal, 2013, Volume 76, Number 3, Page 357
[2]
Yuki Tobimatsu, Sasikumar Elumalai, John H. Grabber, Christy L. Davidson, Xuejun Pan, and John Ralph
ChemSusChem, 2012, Volume 5, Number 4, Page 676
[3]
Yimin Zhu and John Ralph
Tetrahedron Letters, 2011, Volume 52, Number 29, Page 3729
[4]
Betty Cottyn, Albert Kollmann, Pierre Waffo-Teguo, and Paul-Henri Ducrot
Chemistry - A European Journal, 2011, Volume 17, Number 26, Page 7282

Comments (0)

Please log in or register to comment.
Log in