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Volumn 24, Issue 4, 2013, Pages 544-549

Aniline-catalyzed reductive amination as a powerful method for the preparation of reducing end-"clickable" chitooligosaccharides

Author keywords

[No Author keywords available]

Indexed keywords

ANILINE; BIOACTIVITY; FUNCTIONAL MATERIALS; HYDROCARBONS; OLIGOSACCHARIDES; ORGANOCATALYST;

EID: 84876470073     PISSN: 10431802     EISSN: 15204812     Source Type: Journal    
DOI: 10.1021/bc3003716     Document Type: Article
Times cited : (36)

References (36)
  • 1
    • 79951517928 scopus 로고    scopus 로고
    • A perspective on 30 years research on chitin and chitosan
    • Domard, A. (2011) A perspective on 30 years research on chitin and chitosan Carbohydr. Polym. 84, 696-703
    • (2011) Carbohydr. Polym. , vol.84 , pp. 696-703
    • Domard, A.1
  • 2
    • 67349131901 scopus 로고    scopus 로고
    • Chitin and chitosan polymers: Chemistry, solubility and fiber formation
    • Pillai, C. K. S., Paul, W., and Sharma, C. P. (2009) Chitin and chitosan polymers: chemistry, solubility and fiber formation Prog. Polym. Sci. 34, 641-678
    • (2009) Prog. Polym. Sci. , vol.34 , pp. 641-678
    • Pillai, C.K.S.1    Paul, W.2    Sharma, C.P.3
  • 3
    • 0034616855 scopus 로고    scopus 로고
    • Chemical modification of chitosan: Preparation of chitosan-sialic acid branched polysaccharide hybrids
    • Sashiwa, H., Makimura, Y., Shigemasa, Y., and Roy, R. (2000) Chemical modification of chitosan: preparation of chitosan-sialic acid branched polysaccharide hybrids Chem. Commun. 11, 909-910
    • (2000) Chem. Commun. , vol.11 , pp. 909-910
    • Sashiwa, H.1    Makimura, Y.2    Shigemasa, Y.3    Roy, R.4
  • 6
    • 33845461876 scopus 로고    scopus 로고
    • Nucleophilic catalysis of hydrazone formation and transimination: Implications for dynamic covalent chemistry
    • Dirksen, A., Dirksen, S., Hackeng, T. M., and Dawson, P. E. (2006) Nucleophilic catalysis of hydrazone formation and transimination: implications for dynamic covalent chemistry J. Am. Chem. Soc. 128, 15602-15603
    • (2006) J. Am. Chem. Soc. , vol.128 , pp. 15602-15603
    • Dirksen, A.1    Dirksen, S.2    Hackeng, T.M.3    Dawson, P.E.4
  • 7
    • 58149099860 scopus 로고    scopus 로고
    • Rapid oxime and hydrazone ligations with aromatic aldehydes for biomolecular labeling
    • Dirksen, A. and Dawson, P. E. (2008) Rapid oxime and hydrazone ligations with aromatic aldehydes for biomolecular labeling Bioconjugate Chem. 19, 2543-2548
    • (2008) Bioconjugate Chem. , vol.19 , pp. 2543-2548
    • Dirksen, A.1    Dawson, P.E.2
  • 9
    • 34447629377 scopus 로고    scopus 로고
    • Synthesis of ATRP-induced dextran-b-polystyrene diblock copolymers and preliminary investigation of their self-assembly in water
    • Houga, C., Le Meins, J. F., Borsali, R., Taton, D., and Gnanou, Y. (2007) Synthesis of ATRP-induced dextran-b-polystyrene diblock copolymers and preliminary investigation of their self-assembly in water Chem. Commun. 29, 3063-3065
    • (2007) Chem. Commun. , vol.29 , pp. 3063-3065
    • Houga, C.1    Le Meins, J.F.2    Borsali, R.3    Taton, D.4    Gnanou, Y.5
  • 10
    • 33746304118 scopus 로고    scopus 로고
    • Microarrays of heparin oligosaccharides obtained by nitrous acid depolymerization of isolated heparin
    • de Paz, J. L., Spillmann, D., and Seeberger, P. H. (2006) Microarrays of heparin oligosaccharides obtained by nitrous acid depolymerization of isolated heparin Chem. Commun. 29, 3116-3118
    • (2006) Chem. Commun. , vol.29 , pp. 3116-3118
    • De Paz, J.L.1    Spillmann, D.2    Seeberger, P.H.3
  • 11
    • 55149125837 scopus 로고    scopus 로고
    • Syntheses of well-defined glyco-polyorganosiloxanes by "click" chemistry and their surfactant properties
    • Halila, S., Manguian, M., Fort, S., Cottaz, S., Hamaide, T., Fleury, E., and Driguez, H. (2008) Syntheses of well-defined glyco-polyorganosiloxanes by "click" chemistry and their surfactant properties Macromol. Chem. Phys. 209, 1282-1290
    • (2008) Macromol. Chem. Phys. , vol.209 , pp. 1282-1290
    • Halila, S.1    Manguian, M.2    Fort, S.3    Cottaz, S.4    Hamaide, T.5    Fleury, E.6    Driguez, H.7
  • 12
    • 77149126429 scopus 로고    scopus 로고
    • Thermoresponsive vesicular morphologies obtained by self-assemblies of hybrid oligosaccharide-block-poly (N -isopropylacrylamide) copolymer systems
    • Otsuka, I., Fuchise, K., Halila, S., Fort, S., Aissou, K., Pignot-Paintrand, I., Chen, Y., Narumi, A., Kakuchi, T., and Borsali, R. (2010) Thermoresponsive vesicular morphologies obtained by self-assemblies of hybrid oligosaccharide-block-poly (N -isopropylacrylamide) copolymer systems Langmuir 26, 2325-2332
    • (2010) Langmuir , vol.26 , pp. 2325-2332
    • Otsuka, I.1    Fuchise, K.2    Halila, S.3    Fort, S.4    Aissou, K.5    Pignot-Paintrand, I.6    Chen, Y.7    Narumi, A.8    Kakuchi, T.9    Borsali, R.10
  • 13
    • 41749104453 scopus 로고    scopus 로고
    • Preparation of a xanthate-terminated dextran by click chemistry: Application to the synthesis of polysaccharide-coated nanoparticles via surfactant-free ab initio emulsion polymerization of vinyl acetate
    • Bernard, J., Save, M., Arathoon, B., and Charleux, B. (2008) Preparation of a xanthate-terminated dextran by click chemistry: Application to the synthesis of polysaccharide-coated nanoparticles via surfactant-free ab initio emulsion polymerization of vinyl acetate J. Polym. Sci., Part A: Polym. Chem. 46, 2845-2857
    • (2008) J. Polym. Sci., Part A: Polym. Chem. , vol.46 , pp. 2845-2857
    • Bernard, J.1    Save, M.2    Arathoon, B.3    Charleux, B.4
  • 14
    • 0030759788 scopus 로고    scopus 로고
    • Gram scale synthesis of recombinant chitooligosaccharides in Escherichia coli
    • Samain, E., Drouillard, S., Heyraud, A., Driguez, H., and Geremia, R. A. (1997) Gram scale synthesis of recombinant chitooligosaccharides in Escherichia coli Carbohydr. Res. 302, 35-42
    • (1997) Carbohydr. Res. , vol.302 , pp. 35-42
    • Samain, E.1    Drouillard, S.2    Heyraud, A.3    Driguez, H.4    Geremia, R.A.5
  • 15
    • 2942529006 scopus 로고    scopus 로고
    • Ring-opening polymerization of α-chloro-ε-caprolactone and chemical modification of poly(α-chloro-ε-caprolactone) by atom transfer radical processes
    • Lenoir, S., Riva, R., Lou, X., Detrembleur, R., and Lecomte, P. (2004) Ring-opening polymerization of α-chloro-ε-caprolactone and chemical modification of poly(α-chloro-ε-caprolactone) by atom transfer radical processes Macromolecules 37, 4055-4061
    • (2004) Macromolecules , vol.37 , pp. 4055-4061
    • Lenoir, S.1    Riva, R.2    Lou, X.3    Detrembleur, R.4    Lecomte, P.5
  • 16
    • 27944446797 scopus 로고    scopus 로고
    • Combination of ring-opening polymerization and ″click″ chemistry towards functionalization of aliphatic polyesters
    • Riva, R., Schmeeits, S., Stoffelbach, F., Jéroîme, C., Jéroîme, R., and Lecomte, P. (2005) Combination of ring-opening polymerization and ″click″ chemistry towards functionalization of aliphatic polyesters Chem. Commun. 42, 5334-5336
    • (2005) Chem. Commun. , vol.42 , pp. 5334-5336
    • Riva, R.1    Schmeeits, S.2    Stoffelbach, F.3    Jéroîme, C.4    Jéroîme, R.5    Lecomte, P.6
  • 17
    • 0342997609 scopus 로고
    • Ambient-temperature Ullman reaction: 4,5,4′,5′-tetramethoxy- 1,1′-biphenyl-2,2′-dicarboxaldehyde
    • Ziegler, F. E., Fowler, K. W., Rodgers, W. B., and Wester, R. T. (1987) Ambient-temperature Ullman reaction: 4,5,4′,5′-tetramethoxy-1, 1′-biphenyl-2,2′-dicarboxaldehyde Org. Synth. 65, 108-118
    • (1987) Org. Synth. , vol.65 , pp. 108-118
    • Ziegler, F.E.1    Fowler, K.W.2    Rodgers, W.B.3    Wester, R.T.4
  • 18
    • 79551660012 scopus 로고    scopus 로고
    • Pushing the functionality of diamond nanoparticles to new horizons: Orthogonally functionalized nanodiamond using click chemistry
    • Meinhardt, T., Lang, D., Dill, H., and Krueger, H. (2011) Pushing the functionality of diamond nanoparticles to new horizons: orthogonally functionalized nanodiamond using click chemistry Adv. Funct. Mater. 21, 494-500
    • (2011) Adv. Funct. Mater. , vol.21 , pp. 494-500
    • Meinhardt, T.1    Lang, D.2    Dill, H.3    Krueger, H.4
  • 19
    • 0033048084 scopus 로고    scopus 로고
    • Production of O -acetylated and sulfated chitooligosaccharides by recombinant Escherichia coli strains harboring different combinations of nod genes
    • Samain, E., Chazalet, V., and Geremia, R. A. (1999) Production of O -acetylated and sulfated chitooligosaccharides by recombinant Escherichia coli strains harboring different combinations of nod genes J. Biotechnol. 72, 33-47
    • (1999) J. Biotechnol. , vol.72 , pp. 33-47
    • Samain, E.1    Chazalet, V.2    Geremia, R.A.3
  • 20
    • 24044511167 scopus 로고    scopus 로고
    • II-diacetylchitobiose (chitinbiose) and its utilization as a primer for the synthesis of complex carbohydrates
    • II-diacetylchitobiose (chitinbiose) and its utilization as a primer for the synthesis of complex carbohydrates Metab. Eng. 7, 311-317
    • (2005) Metab. Eng. , vol.7 , pp. 311-317
    • Cottaz, S.1    Samain, E.2
  • 22
    • 70350759887 scopus 로고    scopus 로고
    • Analysis of N -acetylaminosugars by CE: A comparative derivatization study
    • Rustighi, I., Campa, C., Rossi, M., Semeraro, S., Vetere, A., and Gamini, A. (2009) Analysis of N -acetylaminosugars by CE: a comparative derivatization study Electrophoresis 30, 2632-2639
    • (2009) Electrophoresis , vol.30 , pp. 2632-2639
    • Rustighi, I.1    Campa, C.2    Rossi, M.3    Semeraro, S.4    Vetere, A.5    Gamini, A.6
  • 23
    • 0030595326 scopus 로고    scopus 로고
    • Reductive amination of N -linked oligosaccharides using organic acid catalysts
    • Evangelista, R. A., Chen, F. -T. A., and Guttman, A. (1996) Reductive amination of N -linked oligosaccharides using organic acid catalysts J. Chromatogr., A 745, 273-280
    • (1996) J. Chromatogr., A , vol.745 , pp. 273-280
    • Evangelista, R.A.1    Chen, F.-T.A.2    Guttman, A.3
  • 24
    • 0029913245 scopus 로고    scopus 로고
    • Acid-catalyzed reductive amination of aldoses with 8-aminopyrene-1,3,6- trisulfonate
    • Evangelista, R. A., Guttman, A., and Chen, F. -T. A. (1996) Acid-catalyzed reductive amination of aldoses with 8-aminopyrene-1,3,6- trisulfonate Electrophoresis 17, 347-351
    • (1996) Electrophoresis , vol.17 , pp. 347-351
    • Evangelista, R.A.1    Guttman, A.2    Chen, F.-T.A.3
  • 25
    • 84981594097 scopus 로고
    • An infrared study of the basicity of non-aromatic imines: Relation to visual pigments
    • Favrot, J., Sandorfy, C., and Vocelle, D. (1978) An infrared study of the basicity of non-aromatic imines: relation to visual pigments Photochem. Photobiol. 28, 271-272
    • (1978) Photochem. Photobiol. , vol.28 , pp. 271-272
    • Favrot, J.1    Sandorfy, C.2    Vocelle, D.3
  • 26
    • 0000352887 scopus 로고
    • The mechanism of Schiff-base formation and hydrolysis
    • Cordes, E. H. and Jencks, W. P. (1962) The mechanism of Schiff-base formation and hydrolysis J. Am. Chem. Soc. 84, 832-837
    • (1962) J. Am. Chem. Soc. , vol.84 , pp. 832-837
    • Cordes, E.H.1    Jencks, W.P.2
  • 27
    • 0001340008 scopus 로고
    • Semicarbazine formation by anilines
    • Cordes, E. H. and Jencks, W. P. (1962) Semicarbazine formation by anilines J. Am. Chem. Soc. 84, 826-831
    • (1962) J. Am. Chem. Soc. , vol.84 , pp. 826-831
    • Cordes, E.H.1    Jencks, W.P.2
  • 29
    • 23944520858 scopus 로고    scopus 로고
    • Capillary electrophoresis separation of a mixture of chitin and chitosan oligosaccharides derivatized using a modified fluorophore conjugation procedure
    • Beaudoin, M. E., Gauthier, J., Boucher, I., and Waldron, K. (2005) Capillary electrophoresis separation of a mixture of chitin and chitosan oligosaccharides derivatized using a modified fluorophore conjugation procedure J. Sep. Sci. 28, 1390-1398
    • (2005) J. Sep. Sci. , vol.28 , pp. 1390-1398
    • Beaudoin, M.E.1    Gauthier, J.2    Boucher, I.3    Waldron, K.4
  • 30
    • 0035847525 scopus 로고    scopus 로고
    • An efficient method for the assembly of sulfated oligosaccharides using reductive amination
    • Koshida, S., Suda, Y., Arano, A., Sobel, M., and Kusumoto, S. (2001) An efficient method for the assembly of sulfated oligosaccharides using reductive amination Tetrahedron Lett. 42, 1293-1296
    • (2001) Tetrahedron Lett. , vol.42 , pp. 1293-1296
    • Koshida, S.1    Suda, Y.2    Arano, A.3    Sobel, M.4    Kusumoto, S.5
  • 32
    • 0035833843 scopus 로고    scopus 로고
    • Novel benzoxazine monomers containing p-phenyl propargyl ether polymerization of monomers and properties of polybenzoxazines
    • Agag, T. and Takeichi, T. (2001) Novel benzoxazine monomers containing p-phenyl propargyl ether polymerization of monomers and properties of polybenzoxazines Macromolecules 34, 7257-7263
    • (2001) Macromolecules , vol.34 , pp. 7257-7263
    • Agag, T.1    Takeichi, T.2
  • 33
    • 0033851083 scopus 로고    scopus 로고
    • A fluorescence-quenched chitopentaose for the study of endo-chitinases and chitobiosidases
    • Cottaz, S., Brasme, B., and Driguez, H. (2000) A fluorescence-quenched chitopentaose for the study of endo-chitinases and chitobiosidases Eur. J. Biochem. 267, 5593-5600
    • (2000) Eur. J. Biochem. , vol.267 , pp. 5593-5600
    • Cottaz, S.1    Brasme, B.2    Driguez, H.3
  • 34
    • 77957559065 scopus 로고    scopus 로고
    • Polysaccharide-containing block copolymers: Synthesis, properties and applications of an emerging family of glycoconjugates
    • Schatz, C. and Lecommandoux, S. (2010) Polysaccharide-containing block copolymers: synthesis, properties and applications of an emerging family of glycoconjugates Macromol. Rapid. Comunm. 31, 1664-1684
    • (2010) Macromol. Rapid. Comunm. , vol.31 , pp. 1664-1684
    • Schatz, C.1    Lecommandoux, S.2
  • 35
    • 77957877175 scopus 로고    scopus 로고
    • Structure-properties relationship of bio-sourced stereocontrolled polytriazoles from click chemistry step growth polymerization of diazide and dialkyne dianhydrohexitols
    • Besset, C., Pascault, J.-P., Fleury, E., Drockenmuller, E., and Bernard, J. (2010) Structure-properties relationship of bio-sourced stereocontrolled polytriazoles from click chemistry step growth polymerization of diazide and dialkyne dianhydrohexitols Biomacromolecules 11, 2797-2803
    • (2010) Biomacromolecules , vol.11 , pp. 2797-2803
    • Besset, C.1    Pascault, J.-P.2    Fleury, E.3    Drockenmuller, E.4    Bernard, J.5


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