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- Title
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).
- Authors
Miyagawa, Yasuyuki; Mizukami, Takahito; Kamitakahara, Hiroshi; Takano, Toshiyuki
- 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 C1β-H1β 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 C1β-H1β bonds of the guaiacyl and p-hydroxyphenyl β-mannosides were close to those derived from the C1α-H1α bonds of the 4- O-methyl-α-D-glucuronic acid moieties described in the literature.
- Subjects
QUANTUM coherence; HETERONUCLEAR diatomic molecules; GLYCOSIDES; BENZALDEHYDE; PHENYL compounds; LIGNINS; CARBOHYDRATES
- Publication
Holzforschung: International Journal of the Biology, Chemistry, Physics, & Technology of Wood, 2014, Vol 68, Issue 7, p747
- ISSN
0018-3830
- Publication type
Article
- DOI
10.1515/hf-2013-0164