Synthesis and molecular recognition of carbohydrate-centered multivalent glycoclusters by a plant lectin RCA120

Bioorganic and Medicinal Chemistry

Volumn 13, Issue 22, 2005, Pages 6151-6157

  Gao, Yongjun ^a   Eguchi, Atsuko ^b   Kakehi, Kazuaki ^b   Lee, Yuan C ^a  

^a JOHNS HOPKINS UNIVERSITY   (United States)

^b KINKI UNIVERSITY   (Japan)

Author keywords

1,3 Cycloaddition reaction; Glycocluster; Lectin RCA120; Molecular recognition

Indexed keywords

CARBOHYDRATE; GLYCOSIDE; LACTOSE; OROSOMUCOID; PLANT LECTIN; PYRANOSIDE;

ARTICLE; CAPILLARY ELECTROPHORESIS; CYCLOADDITION; DRUG BINDING; DRUG SOLUBILITY; DRUG SYNTHESIS; FLUORESCENCE; MOLECULAR RECOGNITION;

AZIDES; CARBOHYDRATE SEQUENCE; ELECTROPHORESIS, CAPILLARY; GLYCOCONJUGATES; GLYCOSIDES; HUMANS; LACTOSE; MOLECULAR SEQUENCE DATA; OROSOMUCOID; PLANT LECTINS; PROTEIN BINDING;

EID: 25844501523     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2005.06.036     Document Type: Article

References (40)

1. A. Varki Glycobiology 3 1993 97
2. H. Lis, and N. Sharon Chem. Rev. 98 1998 637
3. C.R. Bertozzi, and L.L. Kiessling Science 291 2001 2357
4. Y.C. Lee FASEB J. 6 1992 3193
5. Y.C. Lee Carbohydr. Res. 67 1978 509
6. Y.C. Lee, and R.T. Lee Acc. Chem. Res. 28 1995 321
7. P.R. Ashton, R. Köeniger, J.F. Stoddart, D. Alker, and V.D. Harding J. Org. Chem. 61 1996 903
8. A. Marra, M.C. Scherrmann, A. Dondoni, A. Casnati, P. Minari, and R. Ungaro Angew. Chem. 106 1994 2533
9. F.J. Feher, K.D. Wyndham, and D.J. Knauer Chem. Commun. 1998 2393
10. Y. Gao, A. Eguchi, K. Kakehi, and Y.C. Lee Org. Lett. 6 2004 3457
11. R.T. Lee, and Y.C. Lee Bioconjug. Chem. 8 1997 762
12. H. Kamitakahara, T. Suzuki, N. Nishigori, Y. Suzuki, O. Kanie, and C.-H. Wong Angew. Chem. Int. Ed. Engl. 37 1998 1524
13. E.E. Simanek, G.J. McGarvey, J.A. Jablonski, and C.-H. Wong Chem. Rev. 98 1998 833
14. P.I. Kitov, J.M. Sadowska, G. Mulvey, G.D. Armstrong, H. Ling, N.S. Pannu, R.J. Read, and D.R. Bundle Nature 403 2000 669
15. R. Roy, and M.-G. Baek Rev. Mol. Biotechnol. 90 2002 291
16. R. Roy Curr. Opin. Struct. Biol. 6 1996 692
17. C.W. Tornoe, C. Christensen, and J. Meldal J. Org. Chem. 67 2002 3057
18. F. Fazio, M.C. Bryn, O. Blixt, J.C. Paulson, and C.-H. Wong J. Am. Chem. Soc. 124 2002 14397
19. F. Perez-Balderas, M. Ortega-Munoz, J. Morales-Sanfrutos, F. Hernandez-Mateo, F.C. Calvo-Flores, J.A. Calvo-Asin, J. Isac-Garcia, and F. Santoyo-Gonzalez Org. Lett. 5 2003 1951
20. A.E. Speers, G.C. Adam, and B.F. Cravatt J. Am. Chem. Soc. 125 2003 4686
21. K. Nakajima, Y. Oda, M. Kinoshita, and K. Kakehi J. Proteome Res. 2 2003 81
22. C.-H. Wong, X.-S. Ye, and Z. Zhang J. Am. Chem. Soc. 120 1998 7137
23. T. Wunberg, C. Kallus, T. Opatz, S. Henke, W. Schmidt, and H. Kunz Angew. Chem. Int. Ed. Engl. 37 1998 2503
24. M. Dubber, and T.K. Lindhorst Org. Lett. 3 2001 4019
25. B.A. Fenderson, E.M. Eddy, and S.-I. Hakomori Bioessays 12 1990 173
26. L.A. Lasky Annu. Rev. Biochem. 64 1995 113
27. A. Chernyak, S. Oscarson, and D. Turek Carbohydr. Res. 329 2000 309
28. F.W. Lichtenthaler, E. Kaji, and S. Weprek J. Org. Chem. 50 1985 3505
29. P.J. Garegg, and T. Norberg Acta Chem. Scand. B 33 1979 116
30. O.N. Yudina, A.A. Sherman, and N.E. Nifantiev Carbohydr. Res. 332 2001 363
31. O. Blixt, J. Brown, M.J. Schur, W. Wakarchuk, and J.C. Paulson J. Org. Chem. 66 2001 2442
32. R.U. Lemieux, S.Z. Abbas, M.H. Burzynska, and R.M. Ratcliffe Can. J. Chem. 60 1981 63
33. S. Nishimura, K. Matsuoka, T. Furuike, S. Ishii, K. Kurita, and K.M. Nishimura Macromolecules 24 1991 4236
34. T. Yohino, K. Sato, F. Wanme, I. Takai, and Y. Ishido Glycoconjugate J. 9 1992 287
35. H. Mohan, E. Gemma, K. Ruda, and S. Oscarson Synlett 2003 1255
36. V.V. Rostovtsev, L.G. Green, V.V. Fokin, and K.B. Sharpless Angew. Chem. Int. Ed. Engl. 41 2002 2596
37. I.J. Goldstein, and R.D. Poretz Jr. Isolation, physicochemical characterization, and carbohydrate-binding specificity of lectins I.E. Liener N. Sharon I.J. Goldstein The Lectins. Properties, Functions, and Applications in Biology and Medicine 1986 Academic Press Orlando, FL 35 244
38. E.C. Sweeney, A.G. Tonevitsky, D.E. Temiakov, I.I. Agapov, S. Saward, and R.A. Palmer Proteins 28 1997 586
39. K. Kakehi, M. Kinoshita, D. Kawakami, J. Tanaka, K. Sei, K. Endo, Y. Oda, M. Iwaki, and T. Masuko Anal. Chem. 73 2001 2640
40. J.F. McKelvy, and Y.C. Lee Arch. Biochem. Biophys. 132 1969 99