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Biomacromolecules. 2016 Jun 13;17(6):1921-9. doi: 10.1021/acs.biomac.6b00257. Epub 2016 Apr 26.

NMR Assignment for Diaryl Ether Structures (4-O-5 Structures) in Pine Wood Lignin.

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Wood Chemistry Laboratory, Department of Biomaterial Sciences, Graduate School of Agricultural and Life Sciences, The University of Tokyo , Bunkyo-ku, Tokyo 113-8657, Japan.
Japan Science and Technology Agency (JST), PRESTO, Kawaguchi, Saitama 332-0012, Japan.


A 4-O-5-tetramer lignin model compound carrying β-O-4 linkages on each of the side-chain moieties was synthesized, as well as 4-O-5-coupled dehydrodiconiferyl alcohol. By comparison with their NMR data, two cross-signals in the HSQC spectrum of pine milled wood lignin recorded in DMSO-d6 were assigned to H2/C2 and H6/C6 correlations on the aromatic rings of 4-O-5-linked units. Although the H2/C2 correlation peak appeared in the same region as syringyl units, nitrobenzene oxidation of the pine lignin did not yield any syringyl-type product, but did release a 4-O-5-type product.

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