在酚醛末端单元合成带有选择性氘标记甲氧基的 β-O-4 连接模式低聚木酚

IF 2.2 3区农林科学 Q2 FORESTRY

Holzforschung Pub Date : 2024-01-14 DOI:10.1515/hf-2023-0095

Taiki Nishimoto, Kyoka Takagi, Dan Aoki, Kazuhiko Fukushima, Yasuyuki Matsushita

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引用次数: 0

摘要

我们合成了一种木质素模型低聚物，该低聚物只有 β-O-4 连接，并且在酚末端单元上有一个选择性氘标记的甲氧基，以明确低聚木酚酚末端的行为。首先，通过已知的亲核加成法合成 t-丁氧羰基甲基香兰素并使其低聚。然后将低聚物的末端与[3-OCD3]苄基香兰素进行亲核加成，以实现末端单元的选择性标记。通过去苄基化和随后的还原，得到了氘标记的木质素模型低聚物（D-LM）。甲基化后的硫代酸解结果显示，聚合度约为 5，氘标记的苯基丙烷单元仅位于酚醛末端分子。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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Synthesis of β-O-4 linked model oligolignol with a selectively deuterium-labelled methoxy group at the phenolic terminal unit

A lignin model oligomer with only β-O-4 linkages and a selectively deuterium-labelled methoxy group at the phenolic terminal units was synthesised to clarify the behaviour of the phenolic end of oligolignols. First, t-butoxycarbonylmethyl vanillin was synthesised and oligomerised by nucleophilic addition, a known method. The terminal of the oligomers was then subjected to nucleophilic addition to [3-OCD3]benzyl vanillin to achieve selective labelling of the terminal units. A deuterium-labelled lignin model oligomer (D-LM) was obtained through debenzylation and subsequent reduction. The results of thioacidolysis after methylation revealed that the degree of polymerisation was about five, and the deuterium-labelled phenylpropane unit was located only at the phenolic terminal moiety.

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来源期刊

Holzforschung 工程技术-材料科学：纸与木材

CiteScore

4.60

自引率

4.20%

发文量

审稿时长

3.3 months

期刊介绍： Holzforschung is an international scholarly journal that publishes cutting-edge research on the biology, chemistry, physics and technology of wood and wood components. High quality papers about biotechnology and tree genetics are also welcome. Rated year after year as one of the top scientific journals in the category of Pulp and Paper (ISI Journal Citation Index), Holzforschung represents innovative, high quality basic and applied research. The German title reflects the journal''s origins in a long scientific tradition, but all articles are published in English to stimulate and promote cooperation between experts all over the world. Ahead-of-print publishing ensures fastest possible knowledge transfer.