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Volumn 26, Issue 3, 2006, Pages 215-229

Studies on the dehydrogenative polymerizations of monolignol β-glycosides. Part 1. Syntheses of monolignol β-glycosides, (E)-isoconiferin, (E)-isosyringin, and (E)-triandrin

Author keywords

DHP; Imidate method; Isoconiferin; Isosyringin; Lignin; Triandrin

Indexed keywords

DEHYDROGENATION; LIGNIN; POLYMERIZATION; SYNTHESIS (CHEMICAL);

EID: 33747425726     PISSN: 02773813     EISSN: 15322319     Source Type: Journal    
DOI: 10.1080/02773810601023305     Document Type: Article
Times cited : (17)

References (40)
  • 1
    • 0000700532 scopus 로고
    • Effect of the hydrophobic regions of hemicelluloses on dehydrogenative polymerization of sinapyl alcohol
    • Tanahashi, M. and Higuchi, T. (1990) Effect of the hydrophobic regions of hemicelluloses on dehydrogenative polymerization of sinapyl alcohol Mokuzai Gakkaishi, 36(5), pp. 424-428.
    • (1990) Mokuzai Gakkaishi , vol.36 , Issue.5 , pp. 424-428
    • Tanahashi, M.1    Higuchi, T.2
  • 2
    • 0003056602 scopus 로고
    • 2 in a dialysis tube I. Preparation of highly polymerized DHPs
    • 2 in a dialysis tube I. Preparation of highly polymerized DHPs Wood Res., 67, pp. 29-42.
    • (1981) Wood Res. , vol.67 , pp. 29-42
    • Tanahashi, M.1    Higuchi, T.2
  • 3
    • 33747385143 scopus 로고
    • Formation of glycosidic lignin-carbohydrate complex in the enzymatic dehydrogenative polymerization of coniferyl alcohol
    • Kondo, R. and Sako, T. and Iimori, T. and Imamura, H. (1990) Formation of glycosidic lignin-carbohydrate complex in the enzymatic dehydrogenative polymerization of coniferyl alcohol Mokuzai Gakkaishi, 36(4), pp. 332-338.
    • (1990) Mokuzai Gakkaishi , vol.36 , Issue.4 , pp. 332-338
    • Kondo, R.1    Sako, T.2    Iimori, T.3    Imamura, H.4
  • 4
    • 33750691816 scopus 로고
    • Enzymatic degradation of acidic polysaccharide in Bjorkman LCC. I. Presence of glycosidic linkage between lignin and polysaccharide
    • Yaku, F. and Koshijima, T. (1972) Enzymatic degradation of acidic polysaccharide in Bjorkman LCC. I. Presence of glycosidic linkage between lignin and polysaccharide Mokuzai Gakkaishi, 18(10), pp. 519-520.
    • (1972) Mokuzai Gakkaishi , vol.18 , Issue.10 , pp. 519-520
    • Yaku, F.1    Koshijima, T.2
  • 5
    • 85004262813 scopus 로고    scopus 로고
    • The structure and physiological activity of phenyl propanoid glycosides in the Lemon (Citrus limon Burum f.), Unshiu (Citrus unshiu) and Kinkan (Fortunella japonica) peelings
    • Sawabe, A. and Matsubara, Y. and Iizuka, Y. and Okamoto, K. (1998) The structure and physiological activity of phenyl propanoid glycosides in the Lemon (Citrus limon Burum f.), Unshiu (Citrus unshiu) and Kinkan (Fortunella japonica) peelings Nippon Nogeikagaku Kaishi, 62(7), pp. 1067-1071.
    • (1998) Nippon Nogeikagaku Kaishi , vol.62 , Issue.7 , pp. 1067-1071
    • Sawabe, A.1    Matsubara, Y.2    Iizuka, Y.3    Okamoto, K.4
  • 6
    • 0032942885 scopus 로고    scopus 로고
    • Inhibitory effects of constituents from Cynomorium songaricum and related triterpene derivatives on HIV-I protease, Chem
    • Chaomei, M. and Nakamura, N. and Miyashiro, H. and Hattori, M. and Shimamoto, K. (1999) Inhibitory effects of constituents from Cynomorium songaricum and related triterpene derivatives on HIV-I protease, Chem Pharm. Bull., 47(2), pp. 141-145.
    • (1999) Pharm. Bull. , vol.47 , Issue.2 , pp. 141-145
    • Chaomei, M.1    Nakamura, N.2    Miyashiro, H.3    Hattori, M.4    Shimamoto, K.5
  • 8
    • 0001040560 scopus 로고
    • Structure and physiological activity of phenyl propanoid glycosides in Lemon (Citrus limon Burum f.) peel
    • Matsubara, Y. and Yusa, T. and Sawabe, A. and Iizuka, Y. and Okamoto, K. (1991) Structure and physiological activity of phenyl propanoid glycosides in Lemon (Citrus limon Burum f.) peel Agric. Biol. Chem., 55(3), pp. 647-650.
    • (1991) Agric. Biol. Chem. , vol.55 , Issue.3 , pp. 647-650
    • Matsubara, Y.1    Yusa, T.2    Sawabe, A.3    Iizuka, Y.4    Okamoto, K.5
  • 9
    • 0010668065 scopus 로고
    • cis-coniferylalcohol and its glucoside from the bark of beech (Fagus silvatica L.)
    • Harmatha, J. and Lübke, H. and Rybárik, I. and Mahdalik, M. (1978) cis-Coniferyl alcohol and its glucoside from the bark of beech (Fagus silvatica L.) Collection Czechoslov. Chem. Commun., 43, pp. 774-780.
    • (1978) Collection Czechoslov. Chem. Commun. , vol.43 , pp. 774-780
    • Harmatha, J.1    Lübke, H.2    Rybárik, I.3    Mahdalik, M.4
  • 10
    • 0024274895 scopus 로고
    • Exclusive accumulation of Z-isomers of monolignols and their glucosides in bark of Fagus gradifolia
    • Lewis, N. and Inciong, M. and Ohashi, H. and Towers, G. and Yamamoto, E. (1988) Exclusive accumulation of Z-isomers of monolignols and their glucosides in bark of Fagus gradifolia Phytochemistry, 27(7), pp. 2119-2121.
    • (1988) Phytochemistry , vol.27 , Issue.7 , pp. 2119-2121
    • Lewis, N.1    Inciong, M.2    Ohashi, H.3    Towers, G.4    Yamamoto, E.5
  • 11
    • 0343247680 scopus 로고    scopus 로고
    • Phenols from Fagus sylvatica and their role in defence against Cryptococcus fagisuga
    • Dübeler, A. and Voltmer, G. and Gora, V. and Lunderstädt, J. and Zeeck, A. (1997) Phenols from Fagus sylvatica and their role in defence against Cryptococcus fagisuga Phytochemistry, 45(1), pp. 51-57.
    • (1997) Phytochemistry , vol.45 , Issue.1 , pp. 51-57
    • Dübeler, A.1    Voltmer, G.2    Gora, V.3    Lunderstädt, J.4    Zeeck, A.5
  • 12
    • 0000785783 scopus 로고
    • Monolignol glucosides as specific recognition messengers in fugus-plant symbioses
    • Chapela, I. and Petrini, O. and Hagmann, L. (1991) Monolignol glucosides as specific recognition messengers in fugus-plant symbioses Physiological and Molecular Plant Pathology, 39, pp. 289-298.
    • (1991) Physiological and Molecular Plant Pathology , vol.39 , pp. 289-298
    • Chapela, I.1    Petrini, O.2    Hagmann, L.3
  • 14
    • 0008507082 scopus 로고    scopus 로고
    • Structural characterization and antifungal activity of compounds from Pistia stratiotes exudates
    • Dellagreca, M. and Florentino, A. and Monaco, P. and Pinto, G. and Pollio, A. and Previtera, L. and Zarrelli, A. (1998) Structural characterization and antifungal activity of compounds from Pistia stratiotes exudates Allelopathy J., 5(1), pp. 53-66.
    • (1998) Allelopathy J. , vol.5 , Issue.1 , pp. 53-66
    • Dellagreca, M.1    Florentino, A.2    Monaco, P.3    Pinto, G.4    Pollio, A.5    Previtera, L.6    Zarrelli, A.7
  • 15
    • 5844250268 scopus 로고
    • Die Phenolglykoside der Salicaceen
    • Thieme, H. (1963) Die Phenolglykoside der Salicaceen Pharmazie, 18, pp. 770-774.
    • (1963) Pharmazie , vol.18 , pp. 770-774
    • Thieme, H.1
  • 16
    • 0002974170 scopus 로고
    • The effect of the sample preparation method of extractable phenolics of Salicaceae species
    • Julkunen-Tiitto, R. and Tahvanainen, J. (1989) The effect of the sample preparation method of extractable phenolics of Salicaceae species Planta Medica, 55, pp. 55-58.
    • (1989) Planta Medica , vol.55 , pp. 55-58
    • Julkunen-Tiitto, R.1    Tahvanainen, J.2
  • 17
    • 0026687864 scopus 로고
    • Further studies on drying willow (Salix) twigs: The effect of low drying temperature on labile phenolics
    • Julkunen-Tiitto, R. and Gebhardt, K. (1992) Further studies on drying willow (Salix) twigs: The effect of low drying temperature on labile phenolics Planta Medica, 58, pp. 385-387.
    • (1992) Planta Medica , vol.58 , pp. 385-387
    • Julkunen-Tiitto, R.1    Gebhardt, K.2
  • 18
    • 1842640245 scopus 로고    scopus 로고
    • Determination of triandrin and salicin in Salix viminalis L. by reversed-phase high-performance liquid chromatography
    • Minakhmetov, R. and Onuchak, L. and Kurkin, V. and Zapesochnaya, G. and Medvedeva, S. (2002) Determination of triandrin and salicin in Salix viminalis L. by reversed-phase high-performance liquid chromatography Journal of Analytical Chemistry, 57(4), pp. 338-341.
    • (2002) Journal of Analytical Chemistry , vol.57 , Issue.4 , pp. 338-341
    • Minakhmetov, R.1    Onuchak, L.2    Kurkin, V.3    Zapesochnaya, G.4    Medvedeva, S.5
  • 20
    • 0005335107 scopus 로고
    • Exocapric acid and other compounds from tubers and inflorescences of Sarcophyte sanguinea
    • Naidoo, L. and Drewes, S. and Staden, J. and Hutchings, A. (1992) Exocapric acid and other compounds from tubers and inflorescences of Sarcophyte sanguinea Phytochemistry, 31(11), pp. 3929-3931.
    • (1992) Phytochemistry , vol.31 , Issue.11 , pp. 3929-3931
    • Naidoo, L.1    Drewes, S.2    Staden, J.3    Hutchings, A.4
  • 21
    • 0032924664 scopus 로고    scopus 로고
    • A new gallic acid fructose ester from Saxifraga stellaris
    • Chevalley, I. and Marston, A. and Hostettmann, K. (1999) A new gallic acid fructose ester from Saxifraga stellaris Phytochemistry, 50, pp. 151-154.
    • (1999) Phytochemistry , vol.50 , pp. 151-154
    • Chevalley, I.1    Marston, A.2    Hostettmann, K.3
  • 22
    • 0001505450 scopus 로고
    • Glucosylation of lignin precursors by uridine diphosphate glucose: Coniferyl alcohol glucosyltransferase in higher plants
    • Bd
    • Ibrahim, R. (1977) Glucosylation of lignin precursors by uridine diphosphate glucose: Coniferyl alcohol glucosyltransferase in higher plants Z. Pflanzenphysiol, 85, pp. S.253-262. Bd
    • (1977) Z. Pflanzenphysiol , vol.85
    • Ibrahim, R.1
  • 23
    • 0012820835 scopus 로고
    • Enzymatic synthesis of glucosides of monomeric lignin model compounds with commercial β-glucosidase
    • Kondo, R. and Iimori, T. and Imamura, H. (1988) Enzymatic synthesis of glucosides of monomeric lignin model compounds with commercial β-glucosidase Mokuzai Gakkaishi, 34(9), pp. 724-731.
    • (1988) Mokuzai Gakkaishi , vol.34 , Issue.9 , pp. 724-731
    • Kondo, R.1    Iimori, T.2    Imamura, H.3
  • 24
    • 0000249132 scopus 로고
    • High-performance liquid chromatographic separation of E- and Z-monolignols and their glucosides
    • Lewis, N. and Inciong, M. and Dhara, K. and Yamamoto, E. (1989) High-performance liquid chromatographic separation of E- and Z-monolignols and their glucosides Journal of Chromatography, 479, pp. 245-352.
    • (1989) Journal of Chromatography , vol.479 , pp. 245-352
    • Lewis, N.1    Inciong, M.2    Dhara, K.3    Yamamoto, E.4
  • 25
    • 0030734364 scopus 로고    scopus 로고
    • Silica gel-catalyzed β-O-glucosylation of alcohols with 1,2-anhydro-3,4,6-tri-O-pivaloyl-α-D-glucopyranose
    • Matsushita, Y. and Sugamoto, K. and Kita, Y. and Matsui, T. (1997) Silica gel-catalyzed β-O-glucosylation of alcohols with 1,2-anhydro-3,4,6-tri-O-pivaloyl-α-D-glucopyranose Tetrahedron Letters, 38(50), pp. 8709-8712.
    • (1997) Tetrahedron Letters , vol.38 , Issue.50 , pp. 8709-8712
    • Matsushita, Y.1    Sugamoto, K.2    Kita, Y.3    Matsui, T.4
  • 27
    • 0028350514 scopus 로고
    • A mild synthesis of coumaryl, coniferyl, sinapyl aldehydes and alcohols
    • Daubresse, N. and Francesch, C. and Mhamdi, F. and Rolando, C. (1994) A mild synthesis of coumaryl, coniferyl, sinapyl aldehydes and alcohols Synthesis, pp. 369-371.
    • (1994) Synthesis , pp. 369-371
    • Daubresse, N.1    Francesch, C.2    Mhamdi, F.3    Rolando, C.4
  • 28
    • 0003350727 scopus 로고    scopus 로고
    • Facile synthesis of 4-hydroxycinnamyl p-coumarates
    • Lu, F. and Ralph, J. (1998) Facile synthesis of 4-hydroxycinnamyl p-coumarates J. Agric. Food Chem., 46, pp. 2911-2913.
    • (1998) J. Agric. Food Chem. , vol.46 , pp. 2911-2913
    • Lu, F.1    Ralph, J.2
  • 29
    • 84981422033 scopus 로고
    • Glycosidsynthese mit 2,3,4,6-tetra-O-pivaloyl-α-D-glucopyranosylbromid
    • Kunz, H. and Harreus, A. (1982) Glycosidsynthese mit 2,3,4,6-tetra-O-pivaloyl-α-D-glucopyranosylbromid Liebigs. Ann. Chem., pp. 41-48.
    • (1982) Liebigs. Ann. Chem. , pp. 41-48
    • Kunz, H.1    Harreus, A.2
  • 30
    • 0742287093 scopus 로고    scopus 로고
    • Sugar conjugates of fulvestrant (ICI 182,780): Efficient general procedures for glycosylation of the fulvestrant core
    • Thompson, M. and Hutchinson, E. and Stratford, T. and Bowler, W. and Blackburn, G. (2004) Sugar conjugates of fulvestrant (ICI 182,780): Efficient general procedures for glycosylation of the fulvestrant core Tetrahedron Letters, 45, pp. 1207-1210.
    • (2004) Tetrahedron Letters , vol.45 , pp. 1207-1210
    • Thompson, M.1    Hutchinson, E.2    Stratford, T.3    Bowler, W.4    Blackburn, G.5
  • 31
    • 0000541455 scopus 로고
    • Tetra-O-acetyl-α-D-glucopyranosyl bromide
    • In New York and London: Academic Press Inc
    • Lemieux, R. (1963) Tetra-O-acetyl-α-D-glucopyranosyl bromide. In Methods in Carbohydrate Chemistry Volume II. (pp. 221-222). New York and London: Academic Press Inc.
    • (1963) Methods in Carbohydrate Chemistry , vol.2 , pp. 221-222
    • Lemieux, R.1
  • 32
    • 0010441094 scopus 로고
    • Synthese des formentariols. Eine neue mehode zur darstellung von zimtalkoholen
    • Steglich, W. and Zechlin, L. (1978) Synthese des formentariols. Eine neue mehode zur darstellung von zimtalkoholen Chem. Ber., 111, pp. 3939-3948.
    • (1978) Chem. Ber. , vol.111 , pp. 3939-3948
    • Steglich, W.1    Zechlin, L.2
  • 33
    • 0002015726 scopus 로고
    • Chemoselective reduction of carboxylic acids into alcohols using N,N-dimethylchloromethyleniminium chloride and sodium borohydraide
    • Fujiwara, T. and Mori, T. and Sato, T. (1983) Chemoselective reduction of carboxylic acids into alcohols using N,N-dimethylchloromethyleniminium chloride and sodium borohydraide Chemistry Letters, pp. 835-838.
    • (1983) Chemistry Letters , pp. 835-838
    • Fujiwara, T.1    Mori, T.2    Sato, T.3
  • 34
    • 0000865362 scopus 로고
    • Direct and chemoselective conversion of carboxylic acids into aldehydes
    • Fujiwara, T. and Mori, T. and Tsuge, S. and Sato, T. (1983) Direct and chemoselective conversion of carboxylic acids into aldehydes Tetrahedron Letters, 24(14), pp. 1543-1546.
    • (1983) Tetrahedron Letters , vol.24 , Issue.14 , pp. 1543-1546
    • Fujiwara, T.1    Mori, T.2    Tsuge, S.3    Sato, T.4
  • 35
    • 33750707748 scopus 로고
    • Formation of O-glycosidic bond, general discussion
    • In Oxford: Pergamon Press
    • Schuerch, C. (1979) Formation of O-glycosidic bond, general discussion. In Chemistry of the O-glycosidic Bond. (pp. 16-35). Oxford: Pergamon Press.
    • (1979) Chemistry of the O-glycosidic Bond , pp. 16-35
    • Schuerch, C.1
  • 36
    • 33750728729 scopus 로고
    • Koenigs-knorr reactions. Part II. A mechanistic study of mercury (II) cyanide-promoted reactions of 2,3,4,6-tetra-O-methyl-α-D-glucopyranosyl bromide with cyclohexanol in benzene-nitromethane
    • Wallace, J. and Schroeder, L. (1976) Koenigs-knorr reactions. Part II. A mechanistic study of mercury (II) cyanide-promoted reactions of 2,3,4,6-tetra-O-methyl-α-D-glucopyranosyl bromide with cyclohexanol in benzene-nitromethane J. Chem. Soc. Perkin II, pp. 1632-1636.
    • (1976) J. Chem. Soc. Perkin II , pp. 1632-1636
    • Wallace, J.1    Schroeder, L.2
  • 37
    • 33750707748 scopus 로고
    • Formation of O-glycosidic bond, general discussion
    • In Oxford: Pergamon Press
    • Schuerch, C. (1979) Formation of O-glycosidic bond, general discussion. In In Chemistry of the O-glycosidic Bond. (pp. 35-48). Oxford: Pergamon Press.
    • (1979) In Chemistry of the O-glycosidic Bond , pp. 35-48
    • Schuerch, C.1
  • 38
    • 0000013034 scopus 로고
    • An efficient approach to stereoselective glycosylation of ceramide derivatives: Use of pivaloyl group as a stereocontrolling auxiliary
    • Sato, S. and Nunomura, S. and Nakano, T. and Ito, Y. and Ogawa, T. (1988) An efficient approach to stereoselective glycosylation of ceramide derivatives: Use of pivaloyl group as a stereocontrolling auxiliary Tetrahedron Letters, 29(33), pp. 4097-4100.
    • (1988) Tetrahedron Letters , vol.29 , Issue.33 , pp. 4097-4100
    • Sato, S.1    Nunomura, S.2    Nakano, T.3    Ito, Y.4    Ogawa, T.5
  • 39
    • 84985624827 scopus 로고
    • Facile synthesis of α- and β-O-glycosyl imidates; preparation of glycosides and disaccharaides
    • Schmidt, R. and Michel, J. (1980) Facile synthesis of α- and β-O-glycosyl imidates; preparation of glycosides and disaccharaides Angew. Chem. in. Ed. Engl., 19(9), pp. 731-732.
    • (1980) Angew. Chem. In. Ed. Engl. , vol.19 , Issue.9 , pp. 731-732
    • Schmidt, R.1    Michel, J.2
  • 40
    • 0011985729 scopus 로고
    • Synthetic studies of cellulose VI, Effect of the substituent groups of the glycon on β-glycosylation
    • Takano, T. and Harada, Y. and Nakatsubo, F. and Murakami, K. (1990) Synthetic studies of cellulose VI, Effect of the substituent groups of the glycon on β-glycosylation Cellulose Chem. Technol., 24, pp. 333-341.
    • (1990) Cellulose Chem. Technol. , vol.24 , pp. 333-341
    • Takano, T.1    Harada, Y.2    Nakatsubo, F.3    Murakami, K.4


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