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Synthesis of highly deuterated coniferyl alcohol for silencing of NMR signals in the resulting dehydrogenative polymer
| 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 | | Deuteration | | Lignin | | Dehydrogenative polymer | | HSQC |
| 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 |
| URI: | http://hdl.handle.net/2115/86743 |
| 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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