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Synthesis and fundamental HSQC NMR data of monolignol β-glycosides, dihydromonolignol β-glycosides and p-hydroxybenzaldehyde derivative β-glycosides for the analysis of phenyl glycoside type lignin-carbohydrate complexes (LCCs)

  • Yasuyuki Miyagawa EMAIL logo , Takahito Mizukami , Hiroshi Kamitakahara and Toshiyuki Takano
Published/Copyright: February 21, 2014
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Abstract

Twelve monolignol (coniferyl alcohol, sinapyl alcohol and p-coumaryl alcohol) β-glycosides (β-glucosides, β-galactosides, β-xylosides and β-mannosides) were synthesised to obtain fundamental NMR data for the analysis of phenyl glycoside type lignin-carbohydrate complexes (LCCs). That is, the 1,2-trans glycosides (the β-glucosides, β-galactosides and β-xylosides) and the 1,2-cis glycosides (the β-mannosides) were synthesized by means of Koenig-Knorr glycosylation and β-selective Mitsunobu glycosylation strategies, respectively. In addition, dihydromonolignol and p-hydroxybenzaldehyde derivative β-glycosides were also prepared from the corresponding monolignol glycosides and their intermediates, respectively. The correlation observed for the C-H bonds of the sugar moieties in the HSQC spectra of the all β-glycosides varied and were in the range of δC/δH 96–104/4.7–5.4 ppm. Especially, it was found that the correlations derived from the C-H bonds of the guaiacyl and p-hydroxyphenyl β-mannosides were close to those derived from the C-H bonds of the 4-O-methyl-α-D-glucuronic acid moieties described in the literature.


Corresponding author: Yasuyuki Miyagawa, Division of Forest and Biomaterials Science, Graduate School of Agriculture, Kyoto University, Kyoto, Japan, e-mail:

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Received: 2013-8-30
Accepted: 2014-1-27
Published Online: 2014-2-21
Published in Print: 2014-10-1

©2014 by De Gruyter

Articles in the same Issue

  1. Frontmatter
  2. Original Articles
  3. Modeling of alkaline extraction chemistry and kinetics of softwood kraft pulp
  4. Synthesis and fundamental HSQC NMR data of monolignol β-glycosides, dihydromonolignol β-glycosides and p-hydroxybenzaldehyde derivative β-glycosides for the analysis of phenyl glycoside type lignin-carbohydrate complexes (LCCs)
  5. Iridoids from the stems of Viburnum erosum
  6. 6-Pentyl-α-pyrone as an anti-sapstain compound produced by Trichoderma gamsii KUC1747 inhibits the germination of ophiostomatoid fungi
  7. ESR studies on the free radical generation in wood by irradiation with selected sources from UV to IR wavelength regions
  8. Synthesis of aluminum hydroxide thin coating and its influence on the thermomechanical and fire-resistant properties of wood
  9. Lignin distribution in waterlogged archaeological Picea abies (L.) Karst degraded by erosion bacteria
  10. Assessment of covalent bond formation between coupling agents and wood by FTIR spectroscopy and pull strength tests
  11. Effect of hot water extracted hardwood and softwood chips on particleboard properties
  12. The interrelation between microfibril angle (MFA) and hygrothermal recovery (HTR) in compression wood and normal wood of Sugi and Agathis
  13. Chemical remediation of wood treated with micronised, nano or soluble copper preservatives
  14. Energetic investigation of the fatigue of wood
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  16. Short Note
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