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Licensed Unlicensed Requires Authentication Published by De Gruyter January 27, 2021

Reactivity of a benzylic lignin-carbohydrate model compound during enzymatic dehydrogenative polymerisation of coniferyl alcohol

  • Kimiaki Shimizu , Yasuyuki Matsushita EMAIL logo , Dan Aoki , Hayato Mitsuda and Kazuhiko Fukushima
From the journal Holzforschung


Lignin is thought to be covalently bound to carbohydrates like hemicellulose during biosynthesis to form a lignin-carbohydrate complex (LCC). However, successive polymerisation with monolignols after the formation of LCC has not yet been clarified. To investigate the reaction of LCC, its enzymatic dehydrogenative polymerisation was conducted using deuterium-labelled coniferyl alcohol and model compounds, i.e., a lignin model (β-O-4 dimer model) compound (LM) and an LCC model (benzyl ether type) compound (LCCM). The obtained polymers (DHPs) were methylated and subjected to thioacidolysis, and the degradation products were quantified by gas chromatography-mass spectrometry (GC-MS). The results showed that the amount of coniferyl alcohol connected to the LCCM via β-O-4 binding was almost the same as that bound to the LM. However, the amount of unreacted LCCM was larger than that of LM, suggesting that the LCCM is less likely to form condensed structures, i.e., 5-5, β-5, and 4-O-5 structures. This could be due to the steric hindrance of the carbohydrate at the benzylic position.

Corresponding author: Yasuyuki Matsushita, Graduate School of Bioagricultural Sciences, Nagoya University, Nagoya464-8601, Japan, E-mail:

Award Identifier / Grant number: 18H03959

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

  2. Research funding: This research was supported by Japan Society for the Promotion of Science (18H03959).

  3. Conflict of interest statement: The authors declare no conflicts of interest regarding this article.


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Supplementary Material

The online version of this article offers supplementary material (

Received: 2020-09-30
Accepted: 2020-12-15
Published Online: 2021-01-27
Published in Print: 2021-08-26

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