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Synthesis of highly deuterated coniferyl alcohol for silencing of NMR signals in the resulting dehydrogenative polymer

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Title: Synthesis of highly deuterated coniferyl alcohol for silencing of NMR signals in the resulting dehydrogenative polymer
Authors: Shigetomi, Kengo Browse this author →KAKEN DB
Tokizawa, Mana Browse this author
Uraki, Yasumitsu Browse this author →KAKEN DB
Keywords: Coniferyl alcohol
Dehydrogenative polymer
Issue Date: Dec-2022
Publisher: Springer
Journal Title: Journal of wood science
Volume: 68
Issue: 1
Start Page: 45
Publisher DOI: 10.1186/s10086-022-02048-z
Abstract: To establish a facile methodology for the elucidation of the lignin chain-growth mechanism, the preparation of monolignol that does not show NMR signals in the dehydrogenative polymer (DHP) was attempted. As a monolignol of which aliphatic moieties were deuterated, coniferyl alcohol-d(7) was successfully synthesized from protocatechualdehyde and malonic acid via the modified Knoevenagel-Doebner reaction and the Luche reduction. The process achieved high to excellent deuteration efficiencies at the aimed positions (i.e., methoxy: > 99%D, alpha: > 99%D, beta: 92%D, and gamma: 98%D). DHP was prepared solely from coniferyl alcohol-d(7), and its NMR spectra were compared with those from coniferyl alcohol. The results indicated that: (1) the deuterium atoms at methoxy group, alpha- and beta-positions were highly retained even in the DHP, and their signals were effectively suppressed; (2) a part of the deuterium at gamma-position was replaced with H through the reaction; (3) meanwhile, the formation of gamma-CH2 was negligible. This study demonstrated that coniferyl alcohol-d(7) could silence the majority of the signals even when converted to DHP. Highly deuterated monolignols can be a unique molecular tool that can differentiate the signals of interest from those derived from monolignols.
Type: article
Appears in Collections:農学院・農学研究院 (Graduate School of Agriculture / Faculty of Agriculture) > 雑誌発表論文等 (Peer-reviewed Journal Articles, etc)

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