ON THE MECHANISM OF FORMATION OF NONCYCLIC BENZYL ETHERS DURING LIGNIN BIOSYNTHESIS .3. THE REACTIVITY OF A BETA-O-4-TYPE QUINONE METHIDE WITH METHYL-ALPHA-D-GLUCOPYRANOSIDE IN COMPETITION WITH VANILLYL ALCOHOL - THE FORMATION AND THE STABILITY OF BENZYL ETHERS BETWEEN LIGNIN AND CARBOHYDRATES | Health & Environmental Research Online (HERO)

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HERO ID

3579608

Reference Type

Journal Article

Title

ON THE MECHANISM OF FORMATION OF NONCYCLIC BENZYL ETHERS DURING LIGNIN BIOSYNTHESIS .3. THE REACTIVITY OF A BETA-O-4-TYPE QUINONE METHIDE WITH METHYL-ALPHA-D-GLUCOPYRANOSIDE IN COMPETITION WITH VANILLYL ALCOHOL - THE FORMATION AND THE STABILITY OF BENZYL ETHERS BETWEEN LIGNIN AND CARBOHYDRATES

Author(s)

Sipila, J; Brunow, G

Year

1991

Is Peer Reviewed?

Journal

Holzforschung
ISSN: 0018-3830
EISSN: 1437-434X

Volume

Page Numbers

3-7

Web of Science Id

WOS:A1991GM99800003

Abstract

The reactions of a beta-O-4-type quinone methide with methyl-alpha-D-glucopyranoside in the presence of vanillyl alcohol has been determined in water-dioxane solutions of different acidities in order to investigate the formation of LCC during lignin biosynthesis. It was found that the carbohydrate could not compete with phenols or water in reactions with the quinone methide neither in neutral nor in acidic solutions. The products found in these experiments were benzyl aryl ethers, benzyl alcohols and polymers. When the stability of the ether bond between the benzylic carbon and the C-6 of the carbohydrate was investigated, it was found that the linkage was comparatively stable even in moderately acidic or alkaline solutions at ambient temperature. A convenient method for the synthesis of the lignin-carbohydrate model is introduced.

Keywords

LIGNIN BIOSYNTHESIS; LIGNIN MODEL; BETA-O-4 QUINONE METHIDE; LCC; METHYL-ALPHA-D-GLUCOPYRANOSIDE; PHENOLS; ALCOHOLS; H-1 NMR; C-13 NMR; 2-D NMR