Kishimoto Takao, Uraki Yasumitsu, Ubukata Makoto
Laboratory of Wood Chemistry, Research Group of Bioorganic Chemistry, Division of Applied Bioscience, Graduate School of Agriculture, Hokkaido University, Sapporo 060-8589, Japan.
Org Biomol Chem. 2005 Mar 21;3(6):1067-73. doi: 10.1039/b416699j. Epub 2005 Feb 15.
The beta-O-4 structure is the most abundant substructure in lignin. Lignin related polymers composed of only the beta-O-4 structure were prepared using simple aromatic compounds as starting materials. Acetophenone derivatives were brominated, polymerized in the presence of K2CO3 and reduced with NaBH4 to give the lignin related polymers. These are linear polymers which resemble natural lignins in their structures, although they do not have a gamma-hydroxymethyl group. The number average degree of polymerization (DPn) was determined with peracetate of the polymers by gel permeation chromatography. The DPn of guaiacyl type polymers ranged from 15.2-21.4, where the value for the syringyl type was 11.3 and for the p-hydroxyphenyl type 16.9. The Guaiacyl type polymer was very soluble in usual lignin solvents such as 1, 4-dioxane-water (96 : 4, v/v) and DMSO, but only slightly soluble in acetone-water (9 : 1, v/v).
β-O-4结构是木质素中含量最为丰富的亚结构。以简单的芳香族化合物为起始原料制备了仅由β-O-4结构组成的木质素相关聚合物。苯乙酮衍生物经溴化、在碳酸钾存在下聚合，并用硼氢化钠还原，得到木质素相关聚合物。这些是线性聚合物，其结构类似于天然木质素，尽管它们没有γ-羟甲基。通过凝胶渗透色谱法用聚合物的过乙酸酯测定数均聚合度（DPn）。愈创木基型聚合物的DPn范围为15.2 - 21.4，其中紫丁香基型的值为11.3，对羟基苯基型为16.9。愈创木基型聚合物在常用的木质素溶剂如1,4 - 二氧六环 - 水（96 : 4，v/v）和二甲基亚砜中非常易溶，但在丙酮 - 水（9 : 1，v/v）中仅微溶。
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