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Isolation of lignin-carbohydrate bonds in wood: model experiments and preliminary application to pine wood
Luleå University of Technology, Department of Engineering Sciences and Mathematics, Wood Science and Engineering.ORCID iD: 0000-0002-7711-9267
Wood Chemistry Laboratory.
Wood Chemistry Laboratory.
Wood Chemistry Laboratory.
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2004 (English)In: Journal of Wood Science, ISSN 1435-0211, E-ISSN 1611-4663, Vol. 50, no 2, p. 141-150Article in journal (Refereed) Published
Abstract [en]

A novel method for analysis of benzylic ether type lignin-carbohydrate bonds has been developed by using model compounds. Four diastereomers of model compound 3-(4-hydroxy-3-methoxyphenyl)-2-(2-methoxyphenoxy)-3-(methyl -d-glucopyranoside-6-O-yl)-1-propanol (GGMGP), were ozonized in acetic acid/water/methanol 16:3:1 for 1h at 0°C. The product from ozonation of each diastereomer was saponified and the corresponding -etherified tetronic acid (TAMGP) was isolated using ion exchange chromatography. Minor amounts of methyl -d-glucopyranoside (MGP) and small amounts of a gluconic acid etherified with tetronic acid (TAGLCA), tetronic acid, gluconic acid, and glyceric acid were detected in the product mixture of ozonated benzylic ether type model compounds. The results suggest that a benzyl ether bond between lignin and carbohydrate is rather stable during the ozone treatment. Acid treatments with sulfuric acid or trifluoroacetic acid of the derived TAMGP led to cleavage of the glucosidic bond but only a small amount of products (tetronic acid and glucose) resulting from cleavage of the -ether bond were formed. The successful chemical treatments were used for studies of benzylic ether bonds in Japanese red pine. The results suggest the presence of benzylic ether bonds to polysaccharides in the wood.

Place, publisher, year, edition, pages
2004. Vol. 50, no 2, p. 141-150
National Category
Bio Materials
Research subject
Wood Physics
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URN: urn:nbn:se:ltu:diva-3587DOI: 10.1007/s10086-003-0542-xLocal ID: 169d0280-0a8c-11dc-9854-000ea68e967bOAI: oai:DiVA.org:ltu-3587DiVA, id: diva2:976445
Note
Validerad; 2004; 20070525 (cira)Available from: 2016-09-29 Created: 2016-09-29 Last updated: 2017-11-24Bibliographically approved

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Karlsson, Olov

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