Elucidation of LCC bonding sites via γ-TTSA lignin degradation: crude milled wood lignin (MWL) from Eucalyptus globulus for enrichment of lignin xylan linkages and their HSQC-NMR characterization

Daisuke Ando; Fumiaki Nakatsubo; Toshiyuki Takano; Hiroyuki Yano

doi:10.1515/hf-2015-0112

Article

Elucidation of LCC bonding sites via γ-TTSA lignin degradation: crude milled wood lignin (MWL) from Eucalyptus globulus for enrichment of lignin xylan linkages and their HSQC-NMR characterization

Daisuke Ando , Fumiaki Nakatsubo , Toshiyuki Takano and Hiroyuki Yano

Published/Copyright: October 20, 2015

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From the journal Holzforschung Volume 70 Issue 6

Abstract

The selective lignin degradation in a LCC was proceeded with the γ-TTSA method, which is a selective cleavage method for β-O-4 linkages in lignins, in order to obtain more precise information concerning LCC bonding sites. To this purpose, crude MWL from Eucalyptus globulus, containing lignin and xylan, was treated by the γ-TTSA method. This approach consists of four steps: (1) γ-tosylation, (2) thioetherification, (3) sulfonylation, and (4) mild alkali treatment. The degradation products were extracted consecutively with Et₂O, EtOAc, and THF for the lignin removal, and thus the residue was enriched in LCCs. The residue was characterized by HSQC-NMR. Results indicated that the residue contained xylan and β-β substructures, although lignin was degraded. It can be concluded that the β-β substructures play an important role in the bonding sites between lignin and xylan of Eucalyptus globulus.

Keywords: γ-TTSA method; cleavage of β-O-4 linkages; crude milled wood lignin (MWL); HSQC-NMR; lignin carbohydrate complex (LCC); lignin degradation

Corresponding author: Daisuke Ando, Division of Forest and Biomaterials Science, Graduate School of Agriculture, Kyoto University, Kyoto, Japan, Phone: +81-75-753-6256, Fax: +81-75-753-6300, e-mail: andodaisuke@rish.kyoto-u.ac.jp

Acknowledgments

We thank Dr. Kazutsune Tsurumi of Oji Holdings Corporation (Tokyo, Japan) for providing the wood sample of Eucalyptus globulus. We thank Dr. Hiroshi Nishimura and Prof. Masato Katahira for the HSQC-NMR experimental. We thank Dr. Tsukasa Mashima for teaching the sparky soft.

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Received: 2015-5-11

Accepted: 2015-9-15

Published Online: 2015-10-20

Published in Print: 2016-6-1

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Articles in the same Issue

https://doi.org/10.1515/hf-2015-0112

Keywords for this article

γ-TTSA method; cleavage of β-O-4 linkages; crude milled wood lignin (MWL); HSQC-NMR; lignin carbohydrate complex (LCC); lignin degradation