Studies on the dehydrogenative polymerizations (DHPs) of monolignol β-glycosides: Part 4. Horseradish peroxidase-catalyzed copolymerization of isoconiferin and isosyringin
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Yuki Tobimatsu
Abstract
Horseradish peroxidase (HRP)-catalyzed dehydrogenative copolymerization of guaiacyl (G)-type monolignol glycoside (isoconiferin, coniferyl alcohol γ-O-β-d-glucopyranoside, iso-G) and syringyl (S)-type monolignol glycoside (isosyringin, sinapyl alcohol γ-O-β-d-glucopyranoside, iso-S) were performed in continuous dehydrogenation mode (end-wise polymerization) to result in the formation of water-soluble lignin-like copolymers (iso-G/S-DHPs) in a homogeneous phase. The yield of iso-G/S-DHP increased with increasing iso-G content in the mixture of monomers from 23% (iso-G/iso-S 0:100) to 81% (iso-G/iso-S 50:50). The degree of polymerization (DP) of the resulting iso-G/S-DHP also increased proportionally from 7 (iso-G/iso-S 0:100) to 27 (iso-G/iso-S 50:50) as the iso-G content increased. It is obvious that iso-G plays an important role in the polymerization of iso-S. A similar tendency was also observed in conventional copolymerization of coniferyl alcohol (G-alc) and sinapyl alcohol (S-alc). The highest DP for DHP obtained in the conventional system was only ∼10 due to the heterogeneous reaction system. As the HRP-catalyzed monomer consumption rate of iso-S was greatly enhanced by addition of iso-G as a co-monomer, radical transfer from iso-G to iso-S seems to be plausible. Conventional copolymerization of G-alc and S-alc also supports this view. Spectroscopic studies and alkaline nitrobenzene oxidation analyses indicated that iso-G/S-DHPs had typical lignin structures composed of both G and S units. It was confirmed that the copolymerization behavior of the glycosides iso-G and iso-S in a homogeneous phase are well reflected by that of the monolignols G-alc and S-alc in a heterogeneous phase. Results also indicated that the presence of G-type co-monomers sensitively affects the polymerization of S-type monomers.
©2008 by Walter de Gruyter Berlin New York
Articles in the same Issue
- Original Papers
- Studies on the dehydrogenative polymerizations (DHPs) of monolignol β-glycosides: Part 4. Horseradish peroxidase-catalyzed copolymerization of isoconiferin and isosyringin
- Studies on the dehydrogenative polymerization of monolignol β-glycosides: Part 5. UV spectroscopic monitoring of horseradish peroxidase-catalyzed polymerization of monolignol glycosides
- Monolignol dehydrogenative polymerization in vitro in the presence of dioxane and a methylated β-β′ dimer model compound
- Structural characterization of milled wood lignins from different eucalypt species
- FTIR spectroscopy in combination with principal component analysis or cluster analysis as a tool to distinguish beech (Fagus sylvatica L.) trees grown at different sites
- Hydrothermal dissolution of mixed southern hardwoods
- Characterisation of fines from unbleached kraft pulps and their impact on sheet properties
- Effects of refining steam pressure on the properties of loblolly pine (Pinus taeda L.) fibers
- Elastic deformation mechanisms of softwoods in radial tension – Cell wall bending or stretching?
- Fiberboard bending properties as a function of density, thickness, resin, and moisture content
- Modification of Fagus sylvatica (L.) with 1,3-dimethylol-4,5-dihydroxyethylene urea (DMDHEU): Part 1. Estimation of heat adsorption by the isosteric method (Hailwood-Horrobin model) and by solution calorimetry
- Development of wooden block shear wall – Improvement of stiffness by utilizing elements of densified wood
- Significance of the heating rate on the physical properties of carbonized maple wood
- Exploring Scots pine fibre development mechanisms during TMP processing: Impact of cell wall ultrastructure (morphological and topochemical) on negative behaviour
- Pentachlorphenol migration from treated wood exposed to simulated rainfall
- Resistance of Trichoderma harzianum to the biocide tebuconazol – Proposed biodegradation pathways
- Short Notes
- On the variation of acid-labile aryl ether unit content in wood lignin
- Coumarins and secoiridoid glucosides from bark of Fraxinus rhynchophylla Hance
- Antifungal activities of heartwood extracts of Port-Orford cedar extractives
- Antifungal secoabietane dialdehyde and bisabolane-type terpenoids from the heartwood of Cryptomeria japonica D. Don
- Meetings
- Meetings
Articles in the same Issue
- Original Papers
- Studies on the dehydrogenative polymerizations (DHPs) of monolignol β-glycosides: Part 4. Horseradish peroxidase-catalyzed copolymerization of isoconiferin and isosyringin
- Studies on the dehydrogenative polymerization of monolignol β-glycosides: Part 5. UV spectroscopic monitoring of horseradish peroxidase-catalyzed polymerization of monolignol glycosides
- Monolignol dehydrogenative polymerization in vitro in the presence of dioxane and a methylated β-β′ dimer model compound
- Structural characterization of milled wood lignins from different eucalypt species
- FTIR spectroscopy in combination with principal component analysis or cluster analysis as a tool to distinguish beech (Fagus sylvatica L.) trees grown at different sites
- Hydrothermal dissolution of mixed southern hardwoods
- Characterisation of fines from unbleached kraft pulps and their impact on sheet properties
- Effects of refining steam pressure on the properties of loblolly pine (Pinus taeda L.) fibers
- Elastic deformation mechanisms of softwoods in radial tension – Cell wall bending or stretching?
- Fiberboard bending properties as a function of density, thickness, resin, and moisture content
- Modification of Fagus sylvatica (L.) with 1,3-dimethylol-4,5-dihydroxyethylene urea (DMDHEU): Part 1. Estimation of heat adsorption by the isosteric method (Hailwood-Horrobin model) and by solution calorimetry
- Development of wooden block shear wall – Improvement of stiffness by utilizing elements of densified wood
- Significance of the heating rate on the physical properties of carbonized maple wood
- Exploring Scots pine fibre development mechanisms during TMP processing: Impact of cell wall ultrastructure (morphological and topochemical) on negative behaviour
- Pentachlorphenol migration from treated wood exposed to simulated rainfall
- Resistance of Trichoderma harzianum to the biocide tebuconazol – Proposed biodegradation pathways
- Short Notes
- On the variation of acid-labile aryl ether unit content in wood lignin
- Coumarins and secoiridoid glucosides from bark of Fraxinus rhynchophylla Hance
- Antifungal activities of heartwood extracts of Port-Orford cedar extractives
- Antifungal secoabietane dialdehyde and bisabolane-type terpenoids from the heartwood of Cryptomeria japonica D. Don
- Meetings
- Meetings
