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

Author:
Matsushita, Yasuyuki, Okayama, Masaya, Aoki, Dan, Yagami, Sachie, Fukushima, Kazuhiko
Source:
Holzforschung 2019 v.73 no.2 pp. 189-195
ISSN:
1437-434X
Subject:
coniferyl alcohol, dehydrogenation, lignin, molecular weight, polymerization, reaction kinetics
Abstract:
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.
Agid:
6296245