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<p>The 5–5’-type substructure in lignin is an important structure in that it can contribute to molecular branching as well as being condensed structure. To validate the involvement of the 5–5’-type dimer in lignin formation, 5,5’-dehydrodiconiferyl alcohol (bisCA) was synthesized, and its dehydrogenative polymerization was performed in mixed systems with coniferyl alcohol or deuterated ferulic acid (FA-<i>d</i><sub>5</sub>) using horseradish peroxidase–H<sub>2</sub>O<sub>2</sub>. Interestingly, bisCA formed not only copolymers with coniferyl alcohol but also dehydrogenative polymers independently. The resulting products exhibited interunit linkages characteristic of lignin, such as β-β’ or dibenzodioxocin-type linkages. The dehydrogenative polymerization conducted with FA-<i>d</i><sub>5</sub> demonstrated chain growth from both side chains, which is essential for the formation of the internal 5–5’ substructure. These findings suggest that this dimeric substance is capable of contributing to the lignin formation in terms of reactivity.</p>

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5,5’-type coniferyl alcohol dimer as a potential lignin precursor: an investigation of reactivity in dehydrogenative polymerization

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  • 发表日期：

    2025年7月7日

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  • Kengo Shigetomi,
  • Yasumitsu Uraki

摘要

The 5–5’-type substructure in lignin is an important structure in that it can contribute to molecular branching as well as being condensed structure. To validate the involvement of the 5–5’-type dimer in lignin formation, 5,5’-dehydrodiconiferyl alcohol (bisCA) was synthesized, and its dehydrogenative polymerization was performed in mixed systems with coniferyl alcohol or deuterated ferulic acid (FA-d5) using horseradish peroxidase–H2O2. Interestingly, bisCA formed not only copolymers with coniferyl alcohol but also dehydrogenative polymers independently. The resulting products exhibited interunit linkages characteristic of lignin, such as β-β’ or dibenzodioxocin-type linkages. The dehydrogenative polymerization conducted with FA-d5 demonstrated chain growth from both side chains, which is essential for the formation of the internal 5–5’ substructure. These findings suggest that this dimeric substance is capable of contributing to the lignin formation in terms of reactivity.