Reactivity of secondary hydroxyl groups in methyl β-D-xylopyranoside toward a β-O-4-type quinone methide

Journal of Wood Science

Volumn 48, Issue 1, 2002, Pages 32-37

  Kishimoto, Takao ^a,c   Ikeda, Tsutomu ^a,d   Karlsson, Olov ^a,e   Magara, Kengo ^a   Hosoya, Shuji ^a,b  

^a FORESTRY AND FOREST PRODUCTS RESEARCH INSTITUTE   (Japan)

^b UNIVERSITY OF TSUKUBA   (Japan)

^c HOKKAIDO UNIVERSITY   (Japan)

^d NORTH CAROLINA STATE UNIVERSITY   (United States)

^e LULEÅ UNIVERSITY OF TECHNOLOGY   (Sweden)

Author keywords

Lignin carbohydrate complex; Model compound; Ozonation; Xylan; Xylose

Indexed keywords

BIOSYNTHESIS; CARBOHYDRATES; CATALYSTS;

ELUCIDATION;

WOOD;

BIOSYNTHESIS; CARBONATES; CATALYSTS; REACTIVITY; WOOD;

EID: 0042297768     PISSN: 14350211     EISSN: None     Source Type: Journal    
DOI: 10.1007/BF00766235     Document Type: Article

References (15)

1. Taneda H, Nakano J, Hosoya S, Chang H-M (1987) Stability of α-ether type model compounds during chemical pulping processes. J Wood Chem Technol 7:485-498
2. Minor JL (1986) Chemical linkage of polysaccharides to residual lignin in loblolly pine kraft pulp. J Wood Chem Technol 6:185-121
3. Watanabe T, Onishi J, Yamasaki Y, Kaizu S, Koshijima T (1989) Binding-site analysis of the ether linkages between lignin and hemicelluloses in lignin-carbohydrate complexes by DDQ-oxidation. Agric Biol Chem 53:2233-2252
4. Karlsson O, Ikeda T, Kishimoto T, Magara K, Matsumoto Y, Hosoya S (2000) Ozonation of a lignin-carbohydrate complex model compound of the benzyl ether type. J Wood Sci 46:263-265
5. Tanaka K, Nakatsubo F, Higuchi T (1979) Reactions of guaiacylglycerol- β-guaiacyl ether with several sugars. II. Reactions of quinone methide with pyranohexoses. Mokuzai Gakkaishi 25:653-659
6. Tokimatsu T, Umezawa T, Shimada M (1996) Synthesis of four diastereomeric lignin carbohydrate complexes (LCC) model compounds composed of a β-O-4 lignin model linked to methyl β-D-glucoside. Holzforschung 50:156-160
7. Tanahashi M, Higuchi T (1982) Possible formation of LCC via quinone methide intermediates of lignols. In: Proceedings of the Canadian Wood Chemistry Symposium, pp 67-70
8. Toikka M, Sipila J, Teleman A, Brunow G (1998) Lignin-carbohydrate model compounds: formation of lignin-methyl arabinoside and lignin-methyl galactoside benzyl ethers via quinone methide intermediates. J Chem Soc Perkin Trans 1:3813-3818
9. Taneda H, Ishizu A (1989) Reactivity of quinone methide with sugars and lignin model compounds in dimethyl sulfoxide. Mokuzai Gakkaishi 35:996-1000
10. Toikka M, Brunow G (1999) Lignin-carbohydrate model compounds: reactivity of methyl 3-O-(α-L-arabinofuranosyl)-β-D-xylopyranoside and methyl β-D-xylopyranoside towards a β-O-4-quinone methide. J Chem Soc Perkin Trans 1:1877-1883
11. Sipila J, Brunow G (1991) On the mechanism of formation of non-cyclic benzyl ethers during lignin biosynthesis. Part 3. The reactivity of a β-O-4-type quinone methide with methyl-α-D-glucopyranoside in competition with vanillyl alcohol: the formation and the stability of benzyl ethers between lignin and carbohydrates. Holzforschung 45(suppl):3-7
12. 1H NMR spectroscopic investigation of the distribution of erythro and threo forms of β-O-4 structures in lignins. Acta Chem Scand B40:31-35
13. Perrin DD, Dempsey B, Serjeant EP (1981) pKa prediction for organic acids and bases, Chapman & Hall, London
14. Hosoya S, Kanazawa K, Kaneko H, Nakano J (1980) Synthesis of guaiacylglycerol-β-guaiacyl ether. Mokuzai Gakkaishi 26:118-121
15. Ralph J, Young RA (1983) Stereochemical aspects of addition reactions involving lignin model quinone methides. J Wood Chem Technol 3:161-181