4.5 Article

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

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JOURNAL OF WOOD SCIENCE
卷 68, 期 1, 页码 -

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SPRINGER JAPAN KK
DOI: 10.1186/s10086-022-02048-z

关键词

Coniferyl alcohol; Deuteration; Lignin; Dehydrogenative polymer; HSQC

资金

  1. JSPS KAKENHI [19K06161, 21H04730]

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By preparing highly deuterated monolignols, a facile methodology for elucidating the lignin chain-growth mechanism was established. This study demonstrated that highly deuterated monolignols can effectively suppress NMR signals and serve as a unique molecular tool to differentiate signals of interest.
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.

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