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Volumn 8, Issue , 2012, Pages 819-826

High-affinity multivalent wheat germ agglutinin ligands by one-pot click reaction

Author keywords

Carbohydrates; Click chemistry; Cluster effect; Lectins; Multivalency

Indexed keywords


EID: 84861882558     PISSN: None     EISSN: 18605397     Source Type: Journal    
DOI: 10.3762/bjoc.8.91     Document Type: Article
Times cited : (25)

References (60)
  • 1
    • 0001094662 scopus 로고    scopus 로고
    • doi:10.1021/cr940283b
    • Dwek, R. A. Chem. Rev. 1996, 96, 683-720. doi:10.1021/cr940283b
    • (1996) Chem. Rev. , vol.96 , pp. 683-720
    • Dwek, R.A.1
  • 3
    • 0032476812 scopus 로고    scopus 로고
    • doi:10.1002/(SICI)1521-3773(19981102)37:20<2754::AID-ANIE2754>3 .0.CO;2-3
    • Mammen, M.; Choi, S.-K.; Whitesides, G. M. Angew. Chem., Int. Ed. 1998, 37, 2754-2794. doi:10.1002/(SICI)1521-3773(19981102)37:20<2754::AID- ANIE2754>3 .0.CO;2-3
    • (1998) Angew. Chem., Int. Ed. , vol.37 , pp. 2754-2794
    • Mammen, M.1    Choi, S.-K.2    Whitesides, G.M.3
  • 6
    • 8844261143 scopus 로고    scopus 로고
    • Cell surface biology mediated by low affinity multivalent protein-glycan interactions
    • DOI 10.1016/j.cbpa.2004.10.004, PII S136759310400136X
    • Collins, B. E.; Paulson, J. C. Curr. Opin. Chem. Biol. 2004, 8, 617-625. doi:10.1016/j.cbpa.2004.10.004 (Pubitemid 39535723)
    • (2004) Current Opinion in Chemical Biology , vol.8 , Issue.6 , pp. 617-625
    • Collins, B.E.1    Paulson, J.C.2
  • 8
    • 0037012746 scopus 로고    scopus 로고
    • Multivalent cyclooligosaccharides: Versatile carbohydrate clusters with dual role as molecular receptors and lectin ligands
    • DOI 10.1002/1521-3765(20020503)8:9<1982::AID-CHEM1982>3.0.CO;2-5
    • Ortiz Mellet, C.; Defaye, J.; García Fernández, J. M. Chem.-Eur. J. 2002, 8, 1982-1990. doi:10.1002/1521-3765(20020503)8:9<1982:: AID-CHEM1982>3.0.CO;2-5 (Pubitemid 34534421)
    • (2002) Chemistry - A European Journal , vol.8 , Issue.9 , pp. 1982-1990
    • Mellet, C.O.1    Defaye, J.2    Garcia Fernandez, J.M.3
  • 9
    • 0000856193 scopus 로고    scopus 로고
    • doi:10.1007/3-540-45010-6-7
    • Lindhorst, T. K. Top. Curr. Chem. 2002, 218, 201-235. doi:10.1007/3-540-45010-6-7
    • (2002) Top. Curr. Chem. , vol.218 , pp. 201-235
    • Lindhorst, T.K.1
  • 11
    • 49749153118 scopus 로고    scopus 로고
    • doi:10.1021/bi801208b
    • Dam, T. K.; Brewer, C. F. Biochemistry 2008, 47, 8470-8476. doi:10.1021/bi801208b
    • (2008) Biochemistry , vol.47 , pp. 8470-8476
    • Dam, T.K.1    Brewer, C.F.2
  • 12
    • 67449085400 scopus 로고    scopus 로고
    • doi:10.1039/b901828j
    • Pieters, R. J. Org. Biomol. Chem. 2009, 7, 2013-2025. doi:10.1039/b901828j
    • (2009) Org. Biomol. Chem. , vol.7 , pp. 2013-2025
    • Pieters, R.J.1
  • 13
    • 8844220158 scopus 로고    scopus 로고
    • Synthetic approaches to study multivalent carbohydrate-lectin interactions
    • Schmuck, C.; Wennemers, H., Eds.; Wiley-VCH: Weinheim, Germany, doi:10.1002/3527603727.ch2g
    • Wittmann, V. Synthetic Approaches to Study Multivalent Carbohydrate-Lectin Interactions. In Highlights in Bioorganic Chemistry: Methods and Applications; Schmuck, C.; Wennemers, H., Eds.; Wiley-VCH: Weinheim, Germany, 2004; pp 203-213. doi:10.1002/3527603727.ch2g
    • (2004) Highlights in Bioorganic Chemistry: Methods and Applications , pp. 203-213
    • Wittmann, V.1
  • 18
    • 0000358206 scopus 로고
    • doi:10.1021/ar00056a001
    • Lee, Y. C.; Lee, R. T. Acc. Chem. Res. 1995, 28, 321-327. doi:10.1021/ar00056a001
    • (1995) Acc. Chem. Res. , vol.28 , pp. 321-327
    • Lee, Y.C.1    Lee, R.T.2
  • 19
    • 0036462602 scopus 로고    scopus 로고
    • The cluster glycoside effect
    • DOI 10.1021/cr000418f
    • Lundquist, J. J.; Toone, E. J. Chem. Rev. 2002, 102, 555-578. doi:10.1021/cr000418f (Pubitemid 35377623)
    • (2002) Chemical Reviews , vol.102 , Issue.2 , pp. 555-578
    • Lundquist, J.J.1    Toone, E.J.2
  • 22
    • 0032978202 scopus 로고    scopus 로고
    • A model of multivalent ligand-receptor equilibria which explains the effect of multivalent binding inhibitors
    • DOI 10.1016/S0161-5890(98)00116-3, PII S0161589098001163
    • Hubble, J. Mol. Immunol. 1999, 36, 13-18. doi:10.1016/S0161-5890(98) 00116-3 (Pubitemid 29148420)
    • (1999) Molecular Immunology , vol.36 , Issue.1 , pp. 13-18
    • Hubble, J.1
  • 24
    • 0346364990 scopus 로고    scopus 로고
    • Assessment of cooperativity in self-assembly
    • DOI 10.1021/ja038396c
    • Ercolani, G. J. Am. Chem. Soc. 2003, 125, 16097-16103. doi:10.1021/ja038396c (Pubitemid 37553728)
    • (2003) Journal of the American Chemical Society , vol.125 , Issue.51 , pp. 16097-16103
    • Ercolani, G.1
  • 25
    • 0347694971 scopus 로고    scopus 로고
    • On the nature of the multivalency effect: A thermodynamic model
    • DOI 10.1021/ja038223n
    • Kitov, P. I.; Bundle, D. R. J. Am. Chem. Soc. 2003, 125, 16271-16284. doi:10.1021/ja038223n (Pubitemid 38020650)
    • (2003) Journal of the American Chemical Society , vol.125 , Issue.52 , pp. 16271-16284
    • Kitov, P.I.1    Bundle, D.R.2
  • 28
    • 0031104859 scopus 로고    scopus 로고
    • Chemoenzymatic synthesis and lectin binding properties of dendritic N-acetyllactosamine
    • DOI 10.1021/bc970005u
    • Zanini, D.; Roy, R. Bioconjugate Chem. 1997, 8, 187-192. doi:10.1021/bc970005u (Pubitemid 27153292)
    • (1997) Bioconjugate Chemistry , vol.8 , Issue.2 , pp. 187-192
    • Zanini, D.1    Roy, R.2
  • 29
    • 0033238954 scopus 로고    scopus 로고
    • doi:10.1246/cl.1999.69
    • Furuike, T.; Aiba, S. Chem. Lett. 1999, 28, 69-70. doi:10.1246/cl.1999.69
    • (1999) Chem. Lett. , vol.28 , pp. 69-70
    • Furuike, T.1    Aiba, S.2
  • 31
  • 34
    • 35348855865 scopus 로고    scopus 로고
    • Probing multivalent carbohydrate-lectin interactions by an enzyme-linked lectin assay employing covalently immobilized carbohydrates
    • DOI 10.1016/j.bmc.2007.08.063, PII S0968089607007729
    • Maierhofer, C.; Rohmer, K.; Wittmann, V. Bioorg. Med. Chem. 2007, 15, 7661-7676. doi:10.1016/j.bmc.2007.08.063 (Pubitemid 47575921)
    • (2007) Bioorganic and Medicinal Chemistry , vol.15 , Issue.24 , pp. 7661-7676
    • Maierhofer, C.1    Rohmer, K.2    Wittmann, V.3
  • 37
    • 4544296729 scopus 로고    scopus 로고
    • Spatial screening of cyclic neoglycopeptides: Identification of polyvalent wheat-germ agglutinin ligands
    • DOI 10.1002/anie.200352055
    • Wittmann, V.; Seeberger, S. Angew. Chem., Int. Ed. 2004, 43, 900-903. doi:10.1002/anie.200352055 (Pubitemid 39256227)
    • (2004) Angewandte Chemie - International Edition , vol.43 , Issue.7 , pp. 900-903
    • Wittmann, V.1    Seeberger, S.2
  • 38
    • 0034605917 scopus 로고    scopus 로고
    • doi:10.1002/1521-3773(20001201)39:23<4348::AID-ANIE4348>3.0.CO ;2-X
    • Wittmann, V.; Seeberger, S. Angew. Chem., Int. Ed. 2000, 39, 4348-4352. doi:10.1002/1521-3773(20001201)39:23<4348::AID-ANIE4348>3.0.CO ;2-X
    • (2000) Angew. Chem., Int. Ed. , vol.39 , pp. 4348-4352
    • Wittmann, V.1    Seeberger, S.2
  • 39
    • 0019325835 scopus 로고
    • doi:10.1016/0022-2836(80)90181-3
    • Wright, C. S. J. Mol. Biol. 1980, 141, 267-291. doi:10.1016/0022-2836(80) 90181-3
    • (1980) J. Mol. Biol. , vol.141 , pp. 267-291
    • Wright, C.S.1
  • 46
    • 0030037338 scopus 로고    scopus 로고
    • doi:10.1002/pro.5560050803
    • Wright, C. S.; Kellogg, G. E. Protein Sci. 1996, 5, 1466-1476. doi:10.1002/pro.5560050803
    • (1996) Protein Sci. , vol.5 , pp. 1466-1476
    • Wright, C.S.1    Kellogg, G.E.2
  • 47
    • 0027098042 scopus 로고
    • Microcalorimetric study of wheat germ agglutinin binding to N- acetylglucosamine and its oligomers
    • DOI 10.1021/bi00165a012
    • Bains, G.; Lee, R. T.; Lee, Y. C.; Freire, E. Biochemistry 1992, 31, 12624-12628. doi:10.1021/bi00165a012 (Pubitemid 23016529)
    • (1992) Biochemistry , vol.31 , Issue.50 , pp. 12624-12628
    • Bains, G.1    Lee, R.T.2    Lee, Y.C.3    Freire, E.4
  • 50
    • 0037012920 scopus 로고    scopus 로고
    • Peptidotriazoles on solid phase: [1,2,3]-Triazoles by regiospecific copper(I)-catalyzed 1,3-dipolar cycloadditions of terminal alkynes to azides
    • DOI 10.1021/jo011148j
    • Tornøe, C. W.; Christensen, C.; Meldal, M. J. Org. Chem. 2002, 67, 3057-3064. doi:10.1021/jo011148j (Pubitemid 34457265)
    • (2002) Journal of Organic Chemistry , vol.67 , Issue.9 , pp. 3057-3064
    • Tornoe, C.W.1    Christensen, C.2    Meldal, M.3
  • 52
    • 51049094897 scopus 로고    scopus 로고
    • doi:10.1021/cr0783479
    • Meldal, M.; Tornøe, C. W. Chem. Rev. 2008, 108, 2952-3015. doi:10.1021/cr0783479
    • (2008) Chem. Rev. , vol.108 , pp. 2952-3015
    • Meldal, M.1    Tornøe, C.W.2
  • 54
    • 33947493431 scopus 로고    scopus 로고
    • I-catalysed Huisgen azide-alkyne 1,3-dipolar cycloaddition reaction in carbohydrate chemistry
    • DOI 10.1039/b618048p
    • Dedola, S.; Nepogodiev, S. A.; Field, R. A. Org. Biomol. Chem. 2007, 5, 1006-1017. doi:10.1039/b618048p (Pubitemid 46473921)
    • (2007) Organic and Biomolecular Chemistry , vol.5 , Issue.7 , pp. 1006-1017
    • Dedola, S.1    Nepogodiev, S.A.2    Field, R.A.3
  • 55
    • 4444324951 scopus 로고    scopus 로고
    • Polytriazoles as copper(I)-stabilizing ligands in catalysis
    • DOI 10.1021/ol0493094
    • Chan, T. R.; Hilgraf, R.; Sharpless, K. B.; Fokin, V. V. Org. Lett. 2004, 6, 2853-2855. doi:10.1021/ol0493094 (Pubitemid 39178025)
    • (2004) Organic Letters , vol.6 , Issue.17 , pp. 2853-2855
    • Chan, T.R.1    Hilgraf, R.2    Sharpless, K.B.3    Fokin, V.V.4
  • 59
    • 0034000691 scopus 로고    scopus 로고
    • A comparison of biological and calorimetric analyses of multivalent glycodendrimer ligands for concanavalin A
    • DOI 10.1016/S0957-4166(99)00589-3, PII S0957416699005893
    • Corbell, J. B.; Lundquist, J. J.; Toone, E. J. Tetrahedron: Asymmetry 2000, 11, 95-111. doi:10.1016/S0957-4166(99)00589-3 (Pubitemid 30116778)
    • (2000) Tetrahedron Asymmetry , vol.11 , Issue.1 , pp. 95-111
    • Corbell, J.B.1    Lundquist, J.J.2    Toone, E.J.3


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