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On the distribution of the diastereomers of the structural elements in lignins: the steric course of reactions mimicking lignin biosynthesis
University of Helsinki.
Luleå University of Technology, Department of Engineering Sciences and Mathematics, Wood Science and Engineering.ORCID iD: 0000-0002-7711-9267
Chalmers University of Technology.
University of Helsinki.
1993 (English)In: Wood Science and Technology, ISSN 0043-7719, E-ISSN 1432-5225, Vol. 27, no 4, p. 281-286Article in journal (Refereed) Published
Abstract [en]

Stereochemical studies on the formation of the diastereomers of arylglycerol-β-aryl ether structures during lignin biosynthesis have been carried out with model compounds. The addition of water to quinone methides of the β-syringyl ether type gives arylglycerol β-syringyl ethers with a predominance of the erythro isomer when the pH of the medium is low. Since erythro forms of arylglycerol β-syringyl ethers are prevalent in hardwood lignins, this indicates that the pH of the medium in which lignin biosynthesis occurs is lower than has been assumed until now. Equilibration studies with non-phenolic model compounds of the arylglycerolβ-guaiacyl ether and β-syringyl ether types under acidolysis conditions indicate that the erythro predominance observed in the syringyl ethers in lignins does not correspond to equilibrium conditions. A remarkable resistance to acidolysis is observed in the model compounds of etherified syringylglycerol β-syringyl ether type.

Place, publisher, year, edition, pages
1993. Vol. 27, no 4, p. 281-286
National Category
Bio Materials
Research subject
Wood Physics
Identifiers
URN: urn:nbn:se:ltu:diva-5146DOI: 10.1007/BF00195305Local ID: 32d1c260-fe96-11dd-95be-000ea68e967bOAI: oai:DiVA.org:ltu-5146DiVA: diva2:978020
Note
Godkänd; 1993; 20090219 (olokar)Available from: 2016-09-29 Created: 2016-09-29 Last updated: 2017-11-24Bibliographically approved

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