Facile preparation of carbohydrate microarrays by site-specific, covalent immobilization of unmodified carbohydrates on hydrazide-coated glass slides

Organic Letters

Volumn 7, Issue 19, 2005, Pages 4269-4272

  Lee, Myung Ryul ^a   Shin, Injae ^a  

^a Yonsei University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

AMINE; CARBOHYDRATE; GLASS; HYDRAZINE DERIVATIVE; OXYGEN;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; METHODOLOGY; MICROARRAY ANALYSIS;

AMINES; CARBOHYDRATES; GLASS; HYDRAZINES; MICROARRAY ANALYSIS; MOLECULAR STRUCTURE; OXYGEN;

EID: 25444514510     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol051753z     Document Type: Article

References (41)

1. For reviews see: (a) Shin, I.; Park, S.; Lee, M.-r. Chem. Eur. J. 2005, 11, 2894.
2. (b) Shin, I.; Cho, J. W.; Boo, D. W. Comb. Chem. High Throughput Screening 2004, 7, 565.
3. (c) Feizi, T.; Chai, W. Nat. Rev. Mol. Cell. Biol. 2004, 5, 582.
4. (d) Feizi, T.; Fazio, F.; Chai, W.; Wong, C.-H. Curr. Opin. Struct. Biol. 2003, 13, 637.
5. (e) Ortiz Mellet, C.; Garcia Fernández, J. M. ChemBioChem 2002, 3, 819.
6. (f) Love, K. R.; Seeberger, P. H. Angew. Chem., Int. Ed. 2002, 41, 3583.
7. (a) Lee, M.-r.; Shin, I. Angew. Chem., Int. Ed. 2005, 44, 2881.
8. (b) Park, S.; Lee, M.-r.; Pyo, S.-J.; Shin, I. J. Am. Chem. Soc. 2004, 126, 4812.
9. (c) Ratner, D. M.; Adams, E. W.; Su, J.; O'Keefe, B. R.; Mrksich, M.; Seeberger, P. H. ChemBioChem. 2004, 5, 379.
10. (d) Nimrichter, L.; Gargir, A.; Gortler, M.; Altstock, R. T.; Shtevi, A.; Weisshaus, O.; Fire, E.; Dotan, N.; Schnaar, R. L. Glycobiology 2004, 14, 197.
11. (e) Disney, M. D.; Seeberger, P. H. Chem. Biol. 2004, 11, 1701.
12. (f) Bryan, M. C.; Fazio, F.; Lee, H.-K.; Huang, C.-Y.; Chang, A.; Best, M. D.; Calarese, D. A.; Blixt, O.; Paulson, J. C.; Burton, D.; Wilson, I. A.; Wong, C.-H. J. Am. Chem. Soc. 2004, 126, 8640.
13. (g) Blixt, O.; Head, S.; Mondala, T.; Scanlan, C.; Huflejt, M. E.; Alvarez, R.; Bryan, M. C.; Fazio, F.; Calarese, D.; Stevens, J.; Razi, N.; Stevens, D. J.; Skehel, J. J.; van Die, I.; Burton, D. R.; Wilson, I. A.; Cummings, R.; Bovin, N.; Wong, C.-H.; Paulson, J. C. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 17033.
14. (h) Köhn, M.; Wacker, R.; Peters, C.; Schröder, H.; Soulère, L.; Breinbauer, R.; Niemeyer, C. M.; Waldmann, H. Angew. Chem., Int. Ed. 2003, 42, 5829.
15. (i) Schwarz, M.; Spector, L.; Gargir, A.; Shtevi, A.; Gortler, M.; Altstock, R. T.; Dukler, A. A.; Dotan, N. Glycobiology 2003, 13, 749.
16. (j) Park, S.; Shin, I. Angew. Chem., Int. Ed. 2002, 41, 3180.
17. (k) Houseman, B. T.; Mrksich, M. Chem. Biol. 2002, 9, 443.
18. (l) Fazio, F.; Bryan, M. C.; Blixt, O.; Paulson, J. C.; Wong, C.-H. J. Am. Chem. Soc. 2002, 124, 14397.
19. (m) Bryan, M. C.; Plettenburg, O.; Sears, P.; Rabuka, D.; Wacowich-Sgarbi, S.; Wong, C.-H. Chem. Biol. 2002, 9, 713.
20. Fukui, S.; Feizi, T.; Galustian, C.; Lawson, A. M.; Chai, W. Nat. Biotechnol. 2002, 20, 1011.
21. (a) Kawahashi, Y.; Doi, N.; Takashima, H.; Tsuda, C.; Oishi, Y.; Oyama, R.; Yonezawa, M.; Miyamoto-Sato, E.; Yanagawa, H. Proteomics 2003, 3, 1236.
22. (b) Wang, D.; Liu, S.; Trummer, B. J.; Deng, C.; Wang, A. Nat. Biotechnol. 2002, 20, 275.
23. (a) Leteux, C.; Childs, R. A.; Chai, W.; Stoll, M. S.; Kogelberg, H.; Feizi, T. Glycobiology 1998, 8, 227.
24. (b) Shinohara, Y.; Sota, H.; Gotoh, M.; Hasebe, M.; Tosu, M.; Nakao, J.; Hasegawa, Y. Anal. Chem. 1996, 68, 2573.
25. (a) Hatanaka, Y.; Kempin, U.; Park, J.-J. J. Org. Chem. 2000, 65, 5639.
26. (b) Zhao, Y.; Kent, S. B.; Chait, B. T. Proc. Natl. Acad. Sci. U.S.A. 1997, 94, 1629.
27. (c) Cervigni, S. E.; Dumy, P.; Mutter, M. Angew. Chem., Int. Ed. 1996, 35, 1230.
28. Liener, I. E.; Sharon, N.; Goldstein, I. J. The Lectins: Properties, Functions, and Applications in Biology and Medicine; Academic Press: New York, 1986.
29. See the Supporting Information.
30. Reactions between carbohydrates and N-alkylated aminooxy groups generated cyclic adducts predominantly. However, the cyclic adducts were formed in low yield in the case of some carbohydrates. See: (a) Carrasco, M. R.; Brown, R. T.; Serafimova, I. M.; Silva, O. J. Org. Chem. 2003, 68, 195.
31. (b) Carrasco, M. R.; Nguyen, M. J.; Burnell, D. R.; MacLaren, M. D.; Hengel, S. M. Tetrahedron Lett. 2002, 43, 5727.
32. (c) Peri, F.; Dumy, P.; Mutter, M. Tetrahedron 1998, 54, 12269.
33. (a) Ojala, C. R.; Ostman, J. M.; Ojala, W. H. Carbohydr. Res. 2002, 337, 21.
34. (b) Ernholt, B. V.; Thomsen, I. B.; Lohse, A.; Plesner, I. W.; Jensen, K. B.; Hazell, R. G.; Liang, X.; Jakobsen, A.; Bols, M. Chem. Eur. J. 2000, 6, 278.
35. (c) Bendiak, B. Carbohydr. Res. 1997, 304, 85.
36. However, ConA did not recognize mannose, glucose, and N-acetylglucosamine owing to an improper β-configuration at the anomeric position.
37. (a) Connell, H.; Agace, W.; Klemm, P.; Schembri, M.; Marild, S.; Svanborg, C. Proc. Natl. Acad. Sci. U.S.A. 1996, 93, 9827.
38. (b) Durno, C.; Soni, R.; Sherman, P. Clin. Invest. Med. 1989, 12, 194.
39. Harris, S. L.; Spears, P. A.; Havell, E. A.; Hamrick, T. S.; Horton, J. R.; Orndorff, P. E. J. Bacteriol. 2001, 183, 4099.
40. Nagahori, N.; Lee, R. T.; Nishimura, S.-I.; Pagé, D.; Roy, R.; Lee, Y. C. ChemBioChem 2002, 3, 836.
41. The possibility that mannan is immobilized on the surface by nonspecific adsorption is not ruled out. However, lectin binding studies demonstrate that the modified glass slides are suitable for immobilization of this polysaccharide.