Facile synthesis of cyclopeptide-centered multivalent glycoclusters with 'click chemistry' and molecular recognition study by surface plasmon resonance

Bioorganic and Medicinal Chemistry Letters

Volumn 19, Issue 14, 2009, Pages 3775-3778

  Chen, Yong Xiang ^a   Zhao, Lei ^a   Huang, Zhi Ping ^a   Zhao, Yu Fen ^a   Li, Yan Mei ^a  

^a Tsinghua University   (China)

Author keywords

Carbohydrate protein interaction; Click chemistry; Cyclopeptide; Glycocluster; SPR

Indexed keywords

ALKYNE; AZIDE; CONCANAVALIN A; COPPER; CYCLOPEPTIDE; MANNOSE;

ARTICLE; BINDING AFFINITY; CHEMICAL STRUCTURE; CYCLOADDITION; MOLECULAR RECOGNITION; PEPTIDE SYNTHESIS; PROTEIN CARBOHYDRATE INTERACTION; SURFACE PLASMON RESONANCE;

ALKYNES; AZIDES; CATALYSIS; CONCANAVALIN A; COPPER; GLYCOCONJUGATES; PEPTIDES, CYCLIC; PROTEIN BINDING; SURFACE PLASMON RESONANCE;

EID: 67649656011     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2009.04.090     Document Type: Article

References (37)

1. Bertozzi C.R., and Kiessling L.L. Science 291 (2001) 2357
2. Lis H., and Sharon N. Chem. Rev. 98 (1998) 637
3. Lee Y.C., and Lee R.T. Acc. Chem. Res. 28 (1995) 321
4. Mammen M., Choi S.K., and Whitesides G.M. Angew. Chem., Int. Ed. 37 (1998) 2755
5. Ohta T., Miura N., Fujitani N., Nakajima F., Niikura K., Sadamoto R., Guo C.T., Suzuki T., Suzuki Y., Monde K., and Nishimura S.I. Angew. Chem., Int. Ed. 42 (2003) 5186
6. Renaudet O., and Dumy P. Org. Lett. 5 (2003) 243
7. Renaudet O., and Dumy P. Tetrahedron Lett. 45 (2004) 65
8. Renaudet O., and Dumy P. Bioorg. Med. Chem. Lett. 15 (2005) 3619
9. Renaudet O., and Dumy P. Org. Biomol. Chem. 4 (2006) 2628
10. Singh Y., Renaudet O., Defrancq E., and Dumy P. Org. Lett. 7 (2005) 1359
11. Wittmann V., and Seeberger S. Angew. Chem., Int. Ed. 39 (2000) 4348
12. Ambrosi M., Cameron N.R., Davis B.G., and Stolnik S. Org. Biomol. Chem. 3 (2005) 1476
13. Thoma G., Streiff M.B., Katopodis A.G., Duthaler R.O., Voelcker N.H., Ehrhardt C., and Masson C. Chem. Eur. J. 12 (2005) 99
14. Andre S., Kaltner H., Furuike T., Nishimura S.I., and Gabius H.J. Bioconjugate. Chem. 15 (2004) 87
15. Carpenter C., and Nepogodiev S.A. Eur. J. Org. Chem. (2005) 3286
16. Fulton D.A., Pease A.R., and Stoddart J.F. Isr. J. Chem. 40 (2000) 325
17. Fulton D.A., and Stoddart J.F. J. Org. Chem. 66 (2001) 8309
18. Fulton D.A., and Stoddart J.F. Bioconjugate Chem. 12 (2001) 655
19. Dondoni A., and Marra A. J. Org. Chem. 71 (2006) 7546
20. Gao Y.J., Eguchi A., Kakehi K., and Lee Y.C. Bioorg. Med. Chem. 13 (2005) 6151
21. Kohn M., Benito J.M., Mellet C.O., Lindhorst T.K., and Fernandez J.M.G. Chem. Biochem. 5 (2004) 771
22. Kamiya N., Tominaga M., Sato S., and Fujita M. J. Am. Chem. Soc. 129 (2007) 3816
23. Rostovtsev V.V., Green L.G., Fokin V.V., and Sharpless K.B. Angew. Chem., Int. Ed. 41 (2002) 2596
24. Tornoe C.W., Christensen C., and Meldal M. J. Org. Chem. 67 (2002) 3057
25. Dondoni A., Giovannini P.P., and Massi A. Org. Lett. 6 (2004) 2929
26. Lin H.N., and Walsh C.T. J. Am. Chem. Soc. 126 (2004) 13998
27. Joosten J.A.F., Tholen N.T.H., El Maate F.A., Brouwer A.J., van Esse G.W., Rijkers D.T.S., Liskamp R.M.J., and Pieters R.J. Eur. J. Org. Chem. (2005) 3182
28. Cheshev P., Marra A., and Dondoni A. Org. Biomol. Chem. 4 (2006) 3225
29. Gouin S.G., Vanquelef E., Fernandez J.M.G., Mellet C.O., Dupradeau F.Y., and Kovensky J. J. Org. Chem. 72 (2007) 9032
30. Fazio F., Bryan M.C., Blixt O., Paulson J.C., and Wong C.H. J. Am. Chem. Soc. 124 (2002) 14397
31. Vila-Perello M., Gallego R.G., and Andreu D. Chem. Biochem. 6 (2005) 1831
32. Smith E.A., Thomas W.D., Kiessling L.L., and Corn R.M. J. Am. Chem. Soc. 125 (2003) 6140
33. Beccati D., Halkes K.M., Batema G.D., Guillena G., de Souza A.C., van Koten G., and Kamerling J.P. Chem. Biochem. 6 (2005) 1196
34. Al-Mughaid H., and Grindley T.B. J. Org. Chem. 71 (2006) 1390
35. Cioffi E.A. Curr. Top. Med. Chem. 8 (2008) 152
36. Lepore S.D., and He Y. J. Org. Chem. 68 (2003) 8261
37. Babu A.R.S., and Raghunathan R. Tetrahedron Lett. 48 (2007) 6809