Carbohydrate Chips for Studying High-Throughput Carbohydrate-Protein Interactions

Journal of the American Chemical Society

Volumn 126, Issue 15, 2004, Pages 4812-4819

  Park, Sungjin ^a   Lee, Myung Ryul ^a   Pyo, Soon Jin ^a   Shin, Injae ^a  

^a Yonsei University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

BINDING ENERGY; CARBOHYDRATES; GLASS; MATHEMATICAL MODELS; PROTEINS; SYNTHESIS (CHEMICAL);

CARBOHYDRATE CHIPS; CARBOHYDRATE MICROARRAYS; CARBOHYDRATE-PROTEIN INTERACTIONS;

BIOCHEMISTRY;

CARBOHYDRATE; DISACCHARIDE; GLASS; MALEIMIDE; OLIGOSACCHARIDE; PROTEIN; SIALIC ACID DERIVATIVE; THIOL;

ARTICLE; BINDING AFFINITY; CARBOHYDRATE ANALYSIS; COVALENT BOND; DERIVATIZATION; DISSOLUTION; ENZYME GLYCOSYLATION; HIGH THROUGHPUT SCREENING; IC 50; IMMOBILIZATION; LECTIN BINDING; MOLECULAR INTERACTION; MOLECULAR RECOGNITION; QUANTITATIVE ANALYSIS; SYNTHESIS;

CARBOHYDRATE METABOLISM; CARBOHYDRATE SEQUENCE; CARBOHYDRATES; GLYCOSYLATION; LECTINS; MALEIMIDES; MICROCHEMISTRY; MICROSCOPY, FLUORESCENCE; MOLECULAR SEQUENCE DATA; OLIGOSACCHARIDES; PROTEIN BINDING; PROTEINS; SULFHYDRYL COMPOUNDS; SURFACE PROPERTIES;

EID: 1842830161     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0391661     Document Type: Article

References (70)

1. For recent reviews, see (a) Roth, J. Chem. Rev. 2002, 102, 285.
2. (b) Ritchie, G. E.; Moffatt, B. E.; Sim, R. B.; Morgan, B. P.; Dwek, R. A.; Rudd, P. M. Chem. Rev. 2002, 102, 305.
3. (c) Zachara, N. E.; Hart, G. W. Chem. Rev. 2002, 102, 431.
4. (d) Bertozzi, C. R.; Kiessling, L. L. Science 2001, 291, 2357.
5. (a) Danishefsky, S. J.; Allen, J. R. A. Angew. Chem., Int. Ed. 2000, 39, 836.
6. (b) Walker, F.; Vicens, Q.; Westhof, E. Curr. Opin. Chem. Biol. 1999, 3, 694.
7. (c) Sears, P.; Wong, C.-H. Angew. Chem., Int. Ed. 1999, 38, 2300.
8. (a) Mechref, Y.; Novotny, M. V. Chem. Rev. 2002, 102, 321.
9. (b) Wormald, M. P.; Petrescu, A. J.; Pao, Y.-L.; Glithero, A.; Elliott, T.; Dwek, R. A. Chem. Rev. 2002, 102, 371.
10. (c) Vyas, N. K. Curr. Opin. Struct. Biol. 1991, 1, 732.
11. (c) Wyss, D. F.; Choi, J. S.; Li, Jing.; Knoppers, M. H.; Willis, K. J.; Arulanandam, A. R. N.; Smolyar, A.; Reinherz, E. L.; Wagner, G. Science 1995, 269, 1273.
12. (a) Dam, T. K.; Brewer, C. F. Chem. Rev. 2002, 102, 387.
13. (b) Green, R. J.; Frazier, R. A.; Shakesheff, K. M.; Davies, M. C.; Roberts, C. J.; Tendler, S. J. B. Biomaterials 2000, 21, 1823.
14. (c) Mann, D. A.; Kanai, M.; Maly, D. J.; Kiessling, L. L. J. Am. Chem. Soc. 1998, 120, 10575.
15. Lee, Y. C.; Lee, R. T.; Rice, K.; Ichikawa, Y.; Wong, T.-C. Pure Appl. Chem. 1991, 63, 499.
16. (a) Perou, C. M. Nature 2000, 406, 747.
17. (b) Ramsey, G. Nat. Biotechnol. 1998, 16, 40.
18. (c) Marshall, A.; Hodgson, J. Nat. Biotechnol. 1998, 16, 27.
19. (d) DeRisi, J. L.; Lyer, V. R.; Brown, P. O. Science 1997, 278, 680.
20. (a) Templin, M. F.; Stoll, D.; Schrenk, M.; Traub, P. C.; Vöhringer, C. F.; Joos, T. O. Trends Biotechnol. 2002, 20, 160.
21. (b) Weinberger, S. R.; Dalmasso, E. A.; Fung, E. T. Curr. Opin. Chem. Biol. 2001, 6, 86.
22. (a) MacBeath, G.; Schreiber, S. L. Science 2000, 289, 1760.
23. (b) Zhu, H.; Klemic, J. F.; Chang, S.; Bertone, P.; Casamayor, A.; Klemic, K. G.; Smith, D.; Gerstein, M.; Reed, M. A.; Snyder, M. Nat. Genet. 2000, 26, 283.
24. (a) Merchant, M.; Weinberger, S. R. Electrophoresis 2000, 21, 1164.
25. (b) Fung, E. T.; Thulasiraman, V.; Weinberger, S. R.; Dalmasso, E. A. Curr. Opin. Biotech. 2001, 12, 65.
26. (a) Wang, D.; Liu, S.; Trummer, B. J.; Deng, C.; Wang, A. Nat. Biotech. 2002, 20, 275.
27. (b) Fukui, S.; Feizi, T.; Galustian, C.; Lawson, A. M.; Chai, W. Nat. Biotech. 2002, 20, 1011.
28. (c) Houseman, B. T.; Mrksich, M. Chem. Biol. 2002, 9, 443.
29. (d) Park, S.; Shin, I. Angew. Chem., Int. Ed. 2002, 41, 3180.
30. (e) Fazio, F.; Bryan, M. C.; Blixt, O.; Paulson, J. C.; Wong, C.-H. J. Am. Chem. Soc. 2002, 124, 14397.
31. (f) Willats, W. G. T.; Rasmussen, S. E.; Kristensen, T.; Mikkelsen, J. D.; Knox, J. P. Proteomics 2002, 2, 1666.
32. (g) Köhn, M.; Wacker, R. Carsten, P.; Schröder, H.; Soulère, L.; Breinbauer, R.; Niemeyer, C. M.; Waldmann, H. Angew. Chem., Int. Ed. 2003, 42, 5830.
33. (h) Mellet, C. O.; Fernández, J. M. G. ChemBioChem. 2002, 3, 819.
34. (i) Love, K. R.; Seeberger, P. H. Angew. Chem., Int. Ed. 2002, 41, 3583.
35. Reddy, P. Y.; Kondo, S.; Fujita, S.; Toru, T. Synthesis 1998, 999.
36. (a) Shin, I.; Jung, H-j.; Lee, M-r. Tetrahedron Lett. 2001, 42, 1325.
37. (b) Shin, I.; Jung, H.-j.; Cho, J. Bull. Korean Chem. Soc. 2000, 21, 845.
38. Pöchlauer, P.; Hendel, W. Tetrahedron 1998, 54, 3489.
39. (a) Vetter, D.; Gallop, M. A. Bioconjugate Chem. 1995, 6, 316.
40. (b) Vetter, D.; Tate, E. M.; Gallop, M. A. Bioconjugate Chem. 1995, 6, 319.
41. (a) Lee, R. T.; Lee, Y. C. Carbohydr. Res. 1974, 37, 193.
42. (b) Wong, T. C.; Townsend, T. R.; Lee, Y. C. Carbohydr. Res. 1987, 170, 27.
43. (c) Utille, J.-P.; Priem, B. Carbohydr. Res. 2000, 329, 431.
44. (d) Garegg, P. J.; Norberg, T. Carbohydr. Res. 1976, 52, 235.
45. (e) Rosenberg, H. J.; Riley, A. M.; Marwood, R. D.; Correa, V.; Taylor, C. W.; Potter, B. V. L. Carbohydr. Res. 2001, 332, 53.
46. Fitz, W.; Rosenthal, P. B.; Wong, C.-H. Bioorg. Med. Chem. 1996, 4, 1349.
47. The lectin of T. vulgaris (TV) is also known as wheat germ agglutinin (WGA).
48. (a) Liener, I. E.; Sharon, N.; Goldstein, I. J. The Lectins: Properties, Functions, and Applications in Biology and Medicine; Academic Press: Orlando, FL, 1986; pp 35-244.
49. (b) Van Damme, E. J. M.; Psumans, W. J.; Pusztai, A.; Bardocz, S. Handbook of Plant Lectins: Properties and Biomedical Applications; John Wiley & Sons: Chichester, U.K., 1998.
50. For reviews, see (a) Mannen, M.; Choi, S.-K.; Whitesides, G. M. Angew. Chem., Int. Ed. 1998, 37, 2754.
51. (b) Lee, Y. C.; Lee, R. T. Acc. Chem. Res. 1995, 28, 321.
52. d) of methyl α-mannoside, methyl α-glucoside, maltose, methyl α-GlcNAc, and Manα1,6Man-α-OMe for ConA determined by ITC were 0.12, 0.51, 0.76, 0.93, and 0.12 mM, respectively. Mandal, D. K.; Kishore, N.; Brewer, C. F. Biochemistry 1994, 33, 1149.
53. Kaku, H.; Van Damme, E. J. M.; Peumans, W. J.; Goldstein, I. J. Arch. Biochem. Biophys. 1990, 279, 298.
54. Sauerborn, M. K.; Wright, L. M.; Reynolds, C. D.; Grossmann, J. G.; Rizkallah, P. J. J. Mol. Biol. 1999, 290, 185.
55. Kaladas, P. M.; Kabat, E. A.; Iglesias, J. L.; Lis, H.; Sharon, N. Arch. Biochem. Biophys. 1982, 217, 624.
56. (a) Monsigny, M.; Roche, A.-C.; Sene, C.; Maget-Dana, R.; Delmotte, F. Eur. J. Biochem. 1980, 104, 147.
57. (b) Wright, C. S. J. Mol. Biol. 1980, 141, 267.
58. (c) Bhavanandan, V. P.; Kaltlic, A. W. J. Biol. Chem. 1979, 254, 4000.
59. Goldstein, I. J.; Hammarström, S.; Sundblad, G. Biochim. Biophys. Acta 1975, 405, 63.
60. It was reported that AA did not bind to Man up to 50 mM concentration. However, it seems that AA weakly binds to Man on the solid surface maybe because of cluster effect. (a) Kochibe, N.; Furukawa, K. Biochemistry 1980, 19, 2841.
61. (b) Sudakevitz, D.; Imberty, A.; Gilboa-Garber, N. J. Biochem. 2002, 132, 353.
62. (a) Marcaurelle, L. A.; Seeberger, P. H. Curr. Opin. Chem. Biol. 2002, 6, 289.
63. (b) Seeberger, P. H.; Haase, W.-C. Chem. Rev. 2000, 100, 4349.
64. (c) Takahashi, T.; Adachi, M.; Matsuda, A.; Doi, T. Tetrahedron Lett. 2000, 41, 2599.
65. (d) Sofia, M. J. Mol. Divers. 1998, 3, 75.
66. (e) Liang, R.; Yan, L.; Loebach, J.; Ge, M.; Uozumi, Y.; Sekanina, K.; Horan, N.; Gildersleeve, J.; Thompson, C.; Smith, A.; Biswas, K.; Still, W. C.; Kahne, D. Science 1996, 274, 1520.
67. (f) Koeller, K. M.; Wong, C.-H. Chem. Rev. 2000, 100, 4465.
68. Kieburg, C.; Sadalapure, K.; Lindhorst, T. K. Eur. J. Org. Chem. 2000, 2035.
69. Gijsen, H. J. M.; Qiao, L.; Fitz, W.; Wong, C.-H. Chem. Rev. 1996, 96, 443.
70. Seitz, O.; Wong, C.-H. J. Am. Chem. Soc. 1997, 119, 8766.