Macrocyclic glycoclusters. Self-aggregation and phosphate-induced agglutination behaviors of calix[4]resorcarene-based quadruple-chain amphiphiles with a huge oligosaccharide pool

Journal of the American Chemical Society

Volumn 125, Issue 2, 2003, Pages 594-601

  Hayashida, Osamu ^b   Mizuki, Keiji ^b   Akagi, Kazuyuki ^b   Matsuo, Aki ^b   Kanamori, Takuya ^a   Nakai, Takashi ^a   Sando, Shinsuke ^a   Aoyama, Yasuhiro ^a  

^a KYOTO UNIVERSITY   (Japan)

^b KYUSHU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CARBOHYDRATES; GEL PERMEATION CHROMATOGRAPHY; LIGHT SCATTERING; MICELLES; MONOLAYERS; NANOSTRUCTURED MATERIALS; PHOSPHATES; SENSORS; SURFACE PLASMON RESONANCE; TRANSMISSION ELECTRON MICROSCOPY; WATER;

AGGLUTINATION;

AROMATIC COMPOUNDS;

AMPHOPHILE; CALIX[4]RESORCARENE; LACTONE; MACROCYCLIC COMPOUND; NANOPARTICLE; OLIGOSACCHARIDE; PHOSPHATE; SODIUM DIHYDROGEN PHOSPHATE; UNCLASSIFIED DRUG; WATER;

ADSORPTION; ARTICLE; CELL AGGLUTINATION; CELL AGGREGATION; CELL FUNCTION; GEL PERMEATION CHROMATOGRAPHY; HYDROGEN BOND; KINETICS; LIGHT SCATTERING; MICELLE; MOLECULAR INTERACTION; PROTEIN IMMOBILIZATION; SENSOR; SURFACE PLASMON RESONANCE; TRANSMISSION ELECTRON MICROSCOPY;

BRIDGED COMPOUNDS; CARBOHYDRATE SEQUENCE; GLYCOSIDES; GLYCOSYLATION; MICELLES; MODELS, MOLECULAR; MOLECULAR SEQUENCE DATA; OLIGOSACCHARIDES; PARTICLE SIZE; RESORCINOLS; SURFACE PLASMON RESONANCE;

EID: 0013221982     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0275663     Document Type: Article

References (89)

1. (a) Hakomori, S. Pure Appl. Chem. 1991, 63, 473-482.
2. (b) Kobata, A. Acc. Chem. Res. 1993, 26, 319-324.
3. (c) Hakomori, S. Glycoconjugate J. 2000, 17, 627-647.
4. (a) Lee, Y. C.; Townsend, R. R.; Hardy, M. R.; Lonngren, J.; Amarp, J.; Haraldsson, M.; Lonn, H. J. Biol. Chem. 1983, 258, 199-202.
5. (b) Lee, Y. C.; Lee, R. T. Acc. Chem. Res. 1995, 28, 321-327.
6. (a) Nishimura, S.-I.; Matsuoka, K.; Furuike, T.; Ishii, S.; Kurita, K. Macromolecules 1991, 24, 4236-4241.
7. (b) Mortell, K. H.; Gingras, M.; Kiessling, L. L. J. Am. Chem. Soc. 1994, 116, 12053-12054.
8. (c) Lee, W. J.; Spaltenstein, A.; Kingery-Wood, J. E.; Whitesides, G. M. J. Med. Chem. 1994, 37, 3419-3433.
9. (d) Kobayashi, K.; Tsuchida, A.; Usui, T.; Akaike, T. Macromolecules 1997, 30, 2016-2020.
10. (e) Choi, S. K.; Mammen, N.; Whitesides, G. M. J. Am. Chem. Soc. 1997, 119, 4103-4111.
11. (f) Zanini, D.; Roy, R. J. Org. Chem. 1998, 63, 3486-3491.
12. (g) Matsuura, K.; Tsuchida, A.; Okahata, Y.; Akaike, T.; Kobayashi, K. Bull. Chem. Soc. Jpn. 1998, 71, 2973-2977.
13. (h) Gordon, E. J.; Gestwicki, J. E.; Strong, L. E.; Kiessling, L. L. Chem. Biol. 2000, 7, 9-16.
14. (i) Akai, S.; Kajihara, Y.; Nagashima, Y.; Kamei, M.; Arai. J.; Bito, M.; Sato, K. J. Carbohydr. Chem. 2001, 20, 121-143.
15. (j) Cairon. C. W.; Gestwicki, J. E.; Kanai, M.; Kiessling, L. L. J. Am. Chem. Soc. 2002, 124, 1615-1619.
16. (a) Roy, R.; Zanini, Meunier, S. J.; Romanowska, A. J. Chem. Soc., Chem. Commun. 1993, 1869-1870.
17. (b) Roy, R.; Park, W. K. C.; Wu, Q.; Wang, S. N. Tetrahedron Lett. 1995, 36, 4377-4380.
18. (c) Ashton, P. R.; Boyd, S. E.; Brown, C. L.; Jayaraman, N.; Nepogodiev, S. A.; Stoddart, J. F. Chem.-Eur. J. 1996, 2, 1115-1128.
19. (d) Pavlov, G. M.; Korneeva, E. V.; Jumel, K.; Harding, S. E.; Meijer, E. W.; Peerlings, H. W. I.; Stoddart, J. F.; Nepogodiev, S. A. Carbohydr. Polym. 1999, 38. 195-202.
20. (e) Fulton, D. A.; Stoddart, J. F. Org. Lett. 2000, 2, 1113-1116.
21. (f) Aoi, K.; Itoh, K.; Okada, M. Macromolecules 1995, 28, 531-5393.
22. (a) Kingery-Wood, J. E.; Williams, K. W.; Sigal, G. B.; Whitesides, G. M. J. Am. Chem. Soc. 1992, 114, 7303-7305.
23. (b) Zhang, T.; Marchant, R. E. J. Colloid Interface Sci. 1996, 177, 419-426.
24. (a) de la Fuente, Barrientos, A. G.; Rojas, T. C.; Rojo, J.; Canãda, J.; Fernández, A.; Penadés, S. Angew. Chem., Int. Ed. 2001, 40, 2258-2261.
25. (b) Tromas, C.; Rojo, J.; de la Fuente, Barrientos, A. G.; García, R.; Penadés, S. Angew. Chem., Int. Ed. 2001, 40, 3052-3055.
26. (a) Fujimoto, T.; Shimizu, C.; Hayashida, O.; Aoyama, Y. J. Am. Chem. Soc. 1997, 119, 6676-6677.
27. (b) Fujimoto, T.; Shimizu, C.; Hayashida, O.; Aoyama, Y. Gazz. Chim. Ital. 1997, 127, 749-752.
28. (c) Hayashida, O.; Shimizu, C.; Fujimoto, T.; Aoyama, Y. Chem. Lett. 1998, 13-14.
29. (d) Fujimoto, T.; Shimizu, C.; Hayashida, O.; Aoyama, Y. J. Am. Chem. Soc. 1998, 120, 601-602.
30. (e) Ariga, K.; Isoyama, K.; Hayashida, O.; Aoyama, Y.; Okahata, Y. Chem. Lett. 1998, 1007-1008.
31. (f) Aoyama, Y.; Matsuda, Y.; Chuleeraruk, J.; Nishiyama, K.; Fujimoto, T.; Fujimoto, K.; Shimizu, T.; Hayashida, O. Pure Appl. Chem. 1998, 70, 2379-2384.
32. (g) Fujimoto, K.; Hayashida, O.; Aoyama, Y.; Guo, C.-T.; Hidari, K. I.-P. J.; Suzuki, Y. Chem. Lett. 1999, 1259-1260.
33. (h) Hayashida, O.; Kato, M.; Akagi, K.; Aoyama, Y. J. Am. Chem. Soc. 1999, 121, 11597-11598.
34. (i) Fujimoto, K.; Miyata, T.; Aoyama, Y. J. Am. Chem. Soc. 2000, 122, 3558-3559.
35. (j) Hayashida, O.; Matsuo, A.; Aoyama, Y. Chem. Lett. 2001, 272-273.
36. For a calix[4]arene derivative having four side chains with a terminal sugar moiety, see: Marra, A.; Schermann, M.-C.; Dondoni, A.; Casnati, A.; Minari, P.; Ungaro, R. Angew. Chem., Int. Ed. Engl. 1994, 33, 2479-2481.
37. A typical class of glycolipids are sphingoglycolipids in which a fatty acid and an oligosaccharide chain are connected to sphingosine, a long-chain amino alcohol, via amide and glycoside. linkages, respectively.
38. For aggregation behaviors of glycolipids and related saccharide-functionalized amphiphiles, see: (a) Fuhrhop, J.-H.; Helfrich, W. Chem. Rev. 1993, 93, 1565-1582. (b) Vollhardt, D.; Emrich, G.; Gutberlet, T.; Fuhrhop, J.-H. Langmuir 1996, 12, 5659-5663. (c) Fuhrhop, J.-H.; Bedurke, T.; Gnade, M.; Schneider, J.; Doblhofer, K. Langmuir 1997, 13, 455-459. (d) Takeoka, S.; Sou, K.; Boettcher, C.; Fuhrhop, J.-H.; Tsuchida, E. J. Chem. Soc., Faraday Trans. 1998, 94, 2151-2158. (e) Donner, D.; Boettcher, C.; Messerschmidt, C.; Siggel, U.; Fuhrhop, J.-H. Langmuir 1999, 15, 5029-5039. (f) Li, G.; Fudickar, W.; Skupin, M.; Klyszcz, A.; Draeger, C.; Lauer, M.; Fuhrhop, J.-H. Angew. Chem., Int. Ed. 2002, 41, 1828-1852.
39. For aggregation behaviors of glycolipids and related saccharide-functionalized amphiphiles, see: (a) Fuhrhop, J.-H.; Helfrich, W. Chem. Rev. 1993, 93, 1565-1582. (b) Vollhardt, D.; Emrich, G.; Gutberlet, T.; Fuhrhop, J.-H. Langmuir 1996, 12, 5659-5663. (c) Fuhrhop, J.-H.; Bedurke, T.; Gnade, M.; Schneider, J.; Doblhofer, K. Langmuir 1997, 13, 455-459. (d) Takeoka, S.; Sou, K.; Boettcher, C.; Fuhrhop, J.-H.; Tsuchida, E. J. Chem. Soc., Faraday Trans. 1998, 94, 2151-2158. (e) Donner, D.; Boettcher, C.; Messerschmidt, C.; Siggel, U.; Fuhrhop, J.-H. Langmuir 1999, 15, 5029-5039. (f) Li, G.; Fudickar, W.; Skupin, M.; Klyszcz, A.; Draeger, C.; Lauer, M.; Fuhrhop, J.-H. Angew. Chem., Int. Ed. 2002, 41, 1828-1852.
40. For aggregation behaviors of glycolipids and related saccharide-functionalized amphiphiles, see: (a) Fuhrhop, J.-H.; Helfrich, W. Chem. Rev. 1993, 93, 1565-1582. (b) Vollhardt, D.; Emrich, G.; Gutberlet, T.; Fuhrhop, J.-H. Langmuir 1996, 12, 5659-5663. (c) Fuhrhop, J.-H.; Bedurke, T.; Gnade, M.; Schneider, J.; Doblhofer, K. Langmuir 1997, 13, 455-459. (d) Takeoka, S.; Sou, K.; Boettcher, C.; Fuhrhop, J.-H.; Tsuchida, E. J. Chem. Soc., Faraday Trans. 1998, 94, 2151-2158. (e) Donner, D.; Boettcher, C.; Messerschmidt, C.; Siggel, U.; Fuhrhop, J.-H. Langmuir 1999, 15, 5029-5039. (f) Li, G.; Fudickar, W.; Skupin, M.; Klyszcz, A.; Draeger, C.; Lauer, M.; Fuhrhop, J.-H. Angew. Chem., Int. Ed. 2002, 41, 1828-1852.
41. For aggregation behaviors of glycolipids and related saccharide-functionalized amphiphiles, see: (a) Fuhrhop, J.-H.; Helfrich, W. Chem. Rev. 1993, 93, 1565-1582. (b) Vollhardt, D.; Emrich, G.; Gutberlet, T.; Fuhrhop, J.-H. Langmuir 1996, 12, 5659-5663. (c) Fuhrhop, J.-H.; Bedurke, T.; Gnade, M.; Schneider, J.; Doblhofer, K. Langmuir 1997, 13, 455-459. (d) Takeoka, S.; Sou, K.; Boettcher, C.; Fuhrhop, J.-H.; Tsuchida, E. J. Chem. Soc., Faraday Trans. 1998, 94, 2151-2158. (e) Donner, D.; Boettcher, C.; Messerschmidt, C.; Siggel, U.; Fuhrhop, J.-H. Langmuir 1999, 15, 5029-5039. (f) Li, G.; Fudickar, W.; Skupin, M.; Klyszcz, A.; Draeger, C.; Lauer, M.; Fuhrhop, J.-H. Angew. Chem., Int. Ed. 2002, 41, 1828-1852.
42. For aggregation behaviors of glycolipids and related saccharide-functionalized amphiphiles, see: (a) Fuhrhop, J.-H.; Helfrich, W. Chem. Rev. 1993, 93, 1565-1582. (b) Vollhardt, D.; Emrich, G.; Gutberlet, T.; Fuhrhop, J.-H. Langmuir 1996, 12, 5659-5663. (c) Fuhrhop, J.-H.; Bedurke, T.; Gnade, M.; Schneider, J.; Doblhofer, K. Langmuir 1997, 13, 455-459. (d) Takeoka, S.; Sou, K.; Boettcher, C.; Fuhrhop, J.-H.; Tsuchida, E. J. Chem. Soc., Faraday Trans. 1998, 94, 2151-2158. (e) Donner, D.; Boettcher, C.; Messerschmidt, C.; Siggel, U.; Fuhrhop, J.-H. Langmuir 1999, 15, 5029-5039. (f) Li, G.; Fudickar, W.; Skupin, M.; Klyszcz, A.; Draeger, C.; Lauer, M.; Fuhrhop, J.-H. Angew. Chem., Int. Ed. 2002, 41, 1828-1852.
43. For aggregation behaviors of glycolipids and related saccharide-functionalized amphiphiles, see: (a) Fuhrhop, J.-H.; Helfrich, W. Chem. Rev. 1993, 93, 1565-1582. (b) Vollhardt, D.; Emrich, G.; Gutberlet, T.; Fuhrhop, J.-H. Langmuir 1996, 12, 5659-5663. (c) Fuhrhop, J.-H.; Bedurke, T.; Gnade, M.; Schneider, J.; Doblhofer, K. Langmuir 1997, 13, 455-459. (d) Takeoka, S.; Sou, K.; Boettcher, C.; Fuhrhop, J.-H.; Tsuchida, E. J. Chem. Soc., Faraday Trans. 1998, 94, 2151-2158. (e) Donner, D.; Boettcher, C.; Messerschmidt, C.; Siggel, U.; Fuhrhop, J.-H. Langmuir 1999, 15, 5029-5039. (f) Li, G.; Fudickar, W.; Skupin, M.; Klyszcz, A.; Draeger, C.; Lauer, M.; Fuhrhop, J.-H. Angew. Chem., Int. Ed. 2002, 41, 1828-1852.
44. 2 and analogues and binding of polar compounds thereon, see ref 7c.
45. Aoyama, Y.; Tanaka, Y.; Sugahara, S. J. Am. Chem. Soc. 1989, 111, 3397-5404.
46. Böhmer, V. Angew. Chem., Int. Ed. Engl. 1995, 34, 713-745.
47. (a) Williams, T. J.; Plessas, N. R.; Goldstein, I. J. Carbohydr. Res. 1978, 67, C1-C3.
48. (b) Kobayashi, K.; Sumitomo, H.; Ina, Y. Polym. J. 1985, 17, 567-575.
49. 2] ≅ 50 mM (∼20 wt %) when a distinct reduction in surface tension (∼40 dyn/cm) is observed. This may be interpreted in terms of bulk effects.
50. 1s (a) Rayleigh, L. Proc. R. Soc. London 1914, A90, 219-225. (b) Flory, P. J. Principles of Polymer Chemistry; Cornell University Press: New York, 1953; Chapter 7. (c) Taylor, T. W.; Scrivner, S. M.; Sorensen, C. M.; Merklin, J. F. Appl. Opt. 1985, 24, 3713-3717.
51. 1s (a) Rayleigh, L. Proc. R. Soc. London 1914, A90, 219-225. (b) Flory, P. J. Principles of Polymer Chemistry; Cornell University Press: New York, 1953; Chapter 7. (c) Taylor, T. W.; Scrivner, S. M.; Sorensen, C. M.; Merklin, J. F. Appl. Opt. 1985, 24, 3713-3717.
52. 1s (a) Rayleigh, L. Proc. R. Soc. London 1914, A90, 219-225. (b) Flory, P. J. Principles of Polymer Chemistry; Cornell University Press: New York, 1953; Chapter 7. (c) Taylor, T. W.; Scrivner, S. M.; Sorensen, C. M.; Merklin, J. F. Appl. Opt. 1985, 24, 3713-3717.
53. Norgren, M. Math. Comput. Simul. 1999, 50. 553-575.
54. 2 through a membrane filter of 200 nm pores. The chromatogram for the vesicle-free solution thus obtained is the same as that shown in Figure 3, which is actually for an unfiltered solution. Thus, vesicular assemblies if any are only in an undetectable amount, in agreement with the DLS results in reference to the weight- or number-based population.
55. For the hydrogen-bonded saccharide-phosph(on)ate complexes in organic media, see: (a) Das, G.; Hamilton, A. D. J. Am. Chem. Soc. 1994, 116, 11139-11140. (b) Anderson, S.; Neidlein U.; Gramlich, V.; Diederich, F. Angew. Chem., Int. Ed. Engl. 1995, 34, 1596-1599. (c) Coterón, J. M.; hacket, F.; Schneider, H.-J. J. Org. Chem. 1996, 61, 1429-1435. (d) Das, G.; Hamilton. A. D. Tetrahedron, Lett. 1997, 38, 3675-3678. (e) Dondoni, A.; Marra, A.; Schermann, M.-C.; Casnati, A.; Sansone, F.; Ungaro, R. Chem.-Eur. J. 1997, 3, 1774-1782.
56. For the hydrogen-bonded saccharide-phosph(on)ate complexes in organic media, see: (a) Das, G.; Hamilton, A. D. J. Am. Chem. Soc. 1994, 116, 11139-11140. (b) Anderson, S.; Neidlein U.; Gramlich, V.; Diederich, F. Angew. Chem., Int. Ed. Engl. 1995, 34, 1596-1599. (c) Coterón, J. M.; hacket, F.; Schneider, H.-J. J. Org. Chem. 1996, 61, 1429-1435. (d) Das, G.; Hamilton. A. D. Tetrahedron, Lett. 1997, 38, 3675-3678. (e) Dondoni, A.; Marra, A.; Schermann, M.-C.; Casnati, A.; Sansone, F.; Ungaro, R. Chem.-Eur. J. 1997, 3, 1774-1782.
57. For the hydrogen-bonded saccharide-phosph(on)ate complexes in organic media, see: (a) Das, G.; Hamilton, A. D. J. Am. Chem. Soc. 1994, 116, 11139-11140. (b) Anderson, S.; Neidlein U.; Gramlich, V.; Diederich, F. Angew. Chem., Int. Ed. Engl. 1995, 34, 1596-1599. (c) Coterón, J. M.; hacket, F.; Schneider, H.-J. J. Org. Chem. 1996, 61, 1429-1435. (d) Das, G.; Hamilton. A. D. Tetrahedron, Lett. 1997, 38, 3675-3678. (e) Dondoni, A.; Marra, A.; Schermann, M.-C.; Casnati, A.; Sansone, F.; Ungaro, R. Chem.-Eur. J. 1997, 3, 1774-1782.
58. For the hydrogen-bonded saccharide-phosph(on)ate complexes in organic media, see: (a) Das, G.; Hamilton, A. D. J. Am. Chem. Soc. 1994, 116, 11139-11140. (b) Anderson, S.; Neidlein U.; Gramlich, V.; Diederich, F. Angew. Chem., Int. Ed. Engl. 1995, 34, 1596-1599. (c) Coterón, J. M.; hacket, F.; Schneider, H.-J. J. Org. Chem. 1996, 61, 1429-1435. (d) Das, G.; Hamilton, A. D. Tetrahedron, Lett. 1997, 38, 3675-3678. (e) Dondoni, A.; Marra, A.; Schermann, M.-C.; Casnati, A.; Sansone, F.; Ungaro, R. Chem.-Eur. J. 1997, 3, 1774-1782.
59. For the hydrogen-bonded saccharide-phosph(on)ate complexes in organic media, see: (a) Das, G.; Hamilton, A. D. J. Am. Chem. Soc. 1994, 116, 11139-11140. (b) Anderson, S.; Neidlein U.; Gramlich, V.; Diederich, F. Angew. Chem., Int. Ed. Engl. 1995, 34, 1596-1599. (c) Coterón, J. M.; hacket, F.; Schneider, H.-J. J. Org. Chem. 1996, 61, 1429-1435. (d) Das, G.; Hamilton. A. D. Tetrahedron, Lett. 1997, 38, 3675-3678. (e) Dondoni, A.; Marra, A.; Schermann, M.-C.; Casnati, A.; Sansone, F.; Ungaro, R. Chem.-Eur. J. 1997, 3, 1774-1782.
60. For the complexadon of polysaccharides and nucleic acids, see: (a) Sakurai, K.; Shinkai, S. J. Am. Chem. Soc. 2000, 122, 4520-4522. (b) Sakurai, K.; Mizu, M.; Shinkai, S. Biomacromolecules 2001, 2, 641-650.
61. For the complexadon of polysaccharides and nucleic acids, see: (a) Sakurai, K.; Shinkai, S. J. Am. Chem. Soc. 2000, 122, 4520-4522. (b) Sakurai, K.; Mizu, M.; Shinkai, S. Biomacromolecules 2001, 2, 641-650.
62. (a) Kunitake, T.; Okahata, Y.; Shimomura, M.; Yasunami, S.; Takarabe, K. J. Am. Chem. Soc. 1981, 103, 5401-5413.
63. (b) Kunitake, T. Angew. Chem., Int. Ed. Engl. 1992, 31, 709-726.
64. 2.
65. (a) Shinohara, Y.; Kim, F.; Shimizu, M.; Goto, M.; Tosu, M.; Hasegawa, Y. Eur. J. Biochem. 1994, 223, 189-194.
66. (b) Mrksich, M.; Sigal, G. B.; Whitesides, G. M. Langmuir 1995, 11, 4383-4385.
67. (c) Sigal, G. B.; Bamdad, C.; Barberis, A.; Strominger, J.; Whitesides, G. M. Anal. Chem. 1996, 68, 490-497.
68. Karlsson, R.; Fält, A. J. Immunol. Methods 1997, 200, 121-133.
69. Stenberg, E.; Persson, B.; Roos, H.; Urbaniczky, C. J. Colloid Interface Sci. 1991, 143, 513-526.
70. Any unfolded conformation could also account for the calculated surface if intermolecular interpenetration of the oligosaccharide moieties is allowed.
71. For examples of SPR studies on glycocluster compounds, see: (a) MacKenzie, C. R.; Hirama, T.; Lee, K. K.; Altman, E.; Young, N. M. J. Biol. Chem. 1997, 272, 5533-5538. (b) Matsuura, K.; Kitakouji, H.; Sawasa, N.; Ishida, H.; Kiso, M.; Kitajima, K.; Kobayashi, K. J. Am. Chem. Soc. 2000, 122, 7406-7407. (c) Rathore, D.; McCutchan, T. F.; Garboczi, D. N.; Toida, T.; Hernaiz, M. J.; LeBrun, L. A.; Lang, S. C. Biochemistry 2001, 40, 11518-11524. (d) Haseley, S. R.; Vermeer, H. J.; Kamerling, J. P.; Vliegenthart, J. F. G. Proc. Natl. Acad. Sci. U.S.A. 2001, 96, 9419-9424. (e) Hemáiz, M. J.; de la Fuente, J. M.; Barrientos, A. G.; Penadés, S. Angew. Chem., Int. Ed. 2002, 41, 1554-1557.
72. For examples of SPR studies on glycocluster compounds, see: (a) MacKenzie, C. R.; Hirama, T.; Lee, K. K.; Altman, E.; Young, N. M. J. Biol. Chem. 1997, 272, 5533-5538. (b) Matsuura, K.; Kitakouji, H.; Sawasa, N.; Ishida, H.; Kiso, M.; Kitajima, K.; Kobayashi, K. J. Am. Chem. Soc. 2000, 122, 7406-7407. (c) Rathore, D.; McCutchan, T. F.; Garboczi, D. N.; Toida, T.; Hernaiz, M. J.; LeBrun, L. A.; Lang, S. C. Biochemistry 2001, 40, 11518-11524. (d) Haseley, S. R.; Vermeer, H. J.; Kamerling, J. P.; Vliegenthart, J. F. G. Proc. Natl. Acad. Sci. U.S.A. 2001, 96, 9419-9424. (e) Hemáiz, M. J.; de la Fuente, J. M.; Barrientos, A. G.; Penadés, S. Angew. Chem., Int. Ed. 2002, 41, 1554-1557.
73. For examples of SPR studies on glycocluster compounds, see: (a) MacKenzie, C. R.; Hirama, T.; Lee, K. K.; Altman, E.; Young, N. M. J. Biol. Chem. 1997, 272, 5533-5538. (b) Matsuura, K.; Kitakouji, H.; Sawasa, N.; Ishida, H.; Kiso, M.; Kitajima, K.; Kobayashi, K. J. Am. Chem. Soc. 2000, 122, 7406-7407. (c) Rathore, D.; McCutchan, T. F.; Garboczi, D. N.; Toida, T.; Hernaiz, M. J.; LeBrun, L. A.; Lang, S. C. Biochemistry 2001, 40, 11518-11524. (d) Haseley, S. R.; Vermeer, H. J.; Kamerling, J. P.; Vliegenthart, J. F. G. Proc. Natl. Acad. Sci. U.S.A. 2001, 96, 9419-9424. (e) Hemáiz, M. J.; de la Fuente, J. M.; Barrientos, A. G.; Penadés, S. Angew. Chem., Int. Ed. 2002, 41, 1554-1557.
74. For examples of SPR studies on glycocluster compounds, see: (a) MacKenzie, C. R.; Hirama, T.; Lee, K. K.; Altman, E.; Young, N. M. J. Biol. Chem. 1997, 272, 5533-5538. (b) Matsuura, K.; Kitakouji, H.; Sawasa, N.; Ishida, H.; Kiso, M.; Kitajima, K.; Kobayashi, K. J. Am. Chem. Soc. 2000, 122, 7406-7407. (c) Rathore, D.; McCutchan, T. F.; Garboczi, D. N.; Toida, T.; Hernaiz, M. J.; LeBrun, L. A.; Lang, S. C. Biochemistry 2001, 40, 11518-11524. (d) Haseley, S. R.; Vermeer, H. J.; Kamerling, J. P.; Vliegenthart, J. F. G. Proc. Natl. Acad. Sci. U.S.A. 2001, 96, 9419-9424. (e) Hemáiz, M. J.; de la Fuente, J. M.; Barrientos, A. G.; Penadés, S. Angew. Chem., Int. Ed. 2002, 41, 1554-1557.
75. For examples of SPR studies on glycocluster compounds, see: (a) MacKenzie, C. R.; Hirama, T.; Lee, K. K.; Altman, E.; Young, N. M. J. Biol. Chem. 1997, 272, 5533-5538. (b) Matsuura, K.; Kitakouji, H.; Sawasa, N.; Ishida, H.; Kiso, M.; Kitajima, K.; Kobayashi, K. J. Am. Chem. Soc. 2000, 122, 7406-7407. (c) Rathore, D.; McCutchan, T. F.; Garboczi, D. N.; Toida, T.; Hernaiz, M. J.; LeBrun, L. A.; Lang, S. C. Biochemistry 2001, 40, 11518-11524. (d) Haseley, S. R.; Vermeer, H. J.; Kamerling, J. P.; Vliegenthart, J. F. G. Proc. Natl. Acad. Sci. U.S.A. 2001, 96, 9419-9424. (e) Hemáiz, M. J.; de la Fuente, J. M.; Barrientos, A. G.; Penadés, S. Angew. Chem., Int. Ed. 2002, 41, 1554-1557.
76. For monolayers of calix[4]resorcarene derivatives formed on solid supports, see: (a) Adams, H.; Davis, F.; Stirling, C. J. M. J. Chem. Soc., Chem. Commun. 1994, 21, 2527-2529. (b) Thoden van Verzen, E. N.; Engbersen, J. F. J.; de Lange, P. J.; Mahy, J. W. G.; Reinhoudt, D. N. J. Am. Chem. Soc. 1995, 117, 6853-6862. (c) Schoenherr, H.; Vancso, G. J.; Huisman, B.; Frank, C. J. M.; Reinhoudt, D. N. Langmuir 1997, 13, 1567-1570. (d) Ueda, M.; Fukushima, N.; Kudo, K.; Ichimura, K. J. Mater. Chem. 1997, 7, 641-645. (e) Hayashi, Y.; Suzuki, S.; Ichimura, K. J. Mater. Chem. 2001, 11, 1805-1811.
77. For monolayers of calix[4]resorcarene derivatives formed on solid supports, see: (a) Adams, H.; Davis, F.; Stirling, C. J. M. J. Chem. Soc., Chem. Commun. 1994, 21, 2527-2529. (b) Thoden van Verzen, E. N.; Engbersen, J. F. J.; de Lange, P. J.; Mahy, J. W. G.; Reinhoudt, D. N. J. Am. Chem. Soc. 1995, 117, 6853-6862. (c) Schoenherr, H.; Vancso, G. J.; Huisman, B.; Frank, C. J. M.; Reinhoudt, D. N. Langmuir 1997, 13, 1567-1570. (d) Ueda, M.; Fukushima, N.; Kudo, K.; Ichimura, K. J. Mater. Chem. 1997, 7, 641-645. (e) Hayashi, Y.; Suzuki, S.; Ichimura, K. J. Mater. Chem. 2001, 11, 1805-1811.
78. For monolayers of calix[4]resorcarene derivatives formed on solid supports, see: (a) Adams, H.; Davis, F.; Stirling, C. J. M. J. Chem. Soc., Chem. Commun. 1994, 21, 2527-2529. (b) Thoden van Verzen, E. N.; Engbersen, J. F. J.; de Lange, P. J.; Mahy, J. W. G.; Reinhoudt, D. N. J. Am. Chem. Soc. 1995, 117, 6853-6862. (c) Schoenherr, H.; Vancso, G. J.; Huisman, B.; Frank, C. J. M.; Reinhoudt, D. N. Langmuir 1997, 13, 1567-1570. (d) Ueda, M.; Fukushima, N.; Kudo, K.; Ichimura, K. J. Mater. Chem. 1997, 7, 641-645. (e) Hayashi, Y.; Suzuki, S.; Ichimura, K. J. Mater. Chem. 2001, 11, 1805-1811.
79. For monolayers of calix[4]resorcarene derivatives formed on solid supports, see: (a) Adams, H.; Davis, F.; Stirling, C. J. M. J. Chem. Soc., Chem. Commun. 1994, 21, 2527-2529. (b) Thoden van Verzen, E. N.; Engbersen, J. F. J.; de Lange, P. J.; Mahy, J. W. G.; Reinhoudt, D. N. J. Am. Chem. Soc. 1995, 117, 6853-6862. (c) Schoenherr, H.; Vancso, G. J.; Huisman, B.; Frank, C. J. M.; Reinhoudt, D. N. Langmuir 1997, 13, 1567-1570. (d) Ueda, M.; Fukushima, N.; Kudo, K.; Ichimura, K. J. Mater. Chem. 1997, 7, 641-645. (e) Hayashi, Y.; Suzuki, S.; Ichimura, K. J. Mater. Chem. 2001, 11, 1805-1811.
80. For monolayers of calix[4]resorcarene derivatives formed on solid supports, see: (a) Adams, H.; Davis, F.; Stirling, C. J. M. J. Chem. Soc., Chem. Commun. 1994, 21, 2527-2529. (b) Thoden van Verzen, E. N.; Engbersen, J. F. J.; de Lange, P. J.; Mahy, J. W. G.; Reinhoudt, D. N. J. Am. Chem. Soc. 1995, 117, 6853-6862. (c) Schoenherr, H.; Vancso, G. J.; Huisman, B.; Frank, C. J. M.; Reinhoudt, D. N. Langmuir 1997, 13, 1567-1570. (d) Ueda, M.; Fukushima, N.; Kudo, K.; Ichimura, K. J. Mater. Chem. 1997, 7, 641-645. (e) Hayashi, Y.; Suzuki, S.; Ichimura, K. J. Mater. Chem. 2001, 11, 1805-1811.
81. For biorelevant carbohydrate-carbohydrate interactions, see: (a) Eggens, I.; Fendersen, B.; Toyokuni, T.; Dean, B.; Stroud, M.; Hakomori, S. J. Biol. Chem. 1989, 264, 9476-9484. (b) Kojima, N.; Hakomori, S. J. Biol. Chem. 1989, 264, 20159-20162. (c) References 27b,d,e.
82. For biorelevant carbohydrate-carbohydrate interactions, see: (a) Eggens, I.; Fendersen, B.; Toyokuni, T.; Dean, B.; Stroud, M.; Hakomori, S. J. Biol. Chem. 1989, 264, 9476-9484. (b) Kojima, N.; Hakomori, S. J. Biol. Chem. 1989, 264, 20159-20162. (c) References 27b,d,e.
83. For biorelevant carbohydrate-carbohydrate interactions, see: (a) Eggens, I.; Fendersen, B.; Toyokuni, T.; Dean, B.; Stroud, M.; Hakomori, S. J. Biol. Chem. 1989, 264, 9476-9484. (b) Kojima, N.; Hakomori, S. J. Biol. Chem. 1989, 264, 20159-20162. (c) References 27b,d,e.
84. For carbohydrate-carbohydrate interactions in artificial host-guest systems, see: (a) Kikuchi, Y.; Tanaka, Y.; Sutarto, S.; Kobayashi, K.; Toi, H.; Aoyama, Y. J. Am. Chem. Soc. 1992, 114, 10302-10306. (b) Coterón, J. M.; Vicent, C.; Bosso, Penadés, S. J. Am. Chem. Soc. 1993, 115, 10066-10076. (c) Jiménez-Barbero, J.; Junquera, E.; Martín-Pastor, M.; Sharma, S.; Vicent, C.; Penadés, S. J. Am. Chem. Soc. 1995, 117, 11198-11204.
85. For carbohydrate-carbohydrate interactions in artificial host-guest systems, see: (a) Kikuchi, Y.; Tanaka, Y.; Sutarto, S.; Kobayashi, K.; Toi, H.; Aoyama, Y. J. Am. Chem. Soc. 1992, 114, 10302-10306. (b) Coterón, J. M.; Vicent, C.; Bosso, Penadés, S. J. Am. Chem. Soc. 1993, 115, 10066-10076. (c) Jiménez-Barbero, J.; Junquera, E.; Martín-Pastor, M.; Sharma, S.; Vicent, C.; Penadés, S. J. Am. Chem. Soc. 1995, 117, 11198-11204.
86. For carbohydrate-carbohydrate interactions in artificial host-guest systems, see: (a) Kikuchi, Y.; Tanaka, Y.; Sutarto, S.; Kobayashi, K.; Toi, H.; Aoyama, Y. J. Am. Chem. Soc. 1992, 114, 10302-10306. (b) Coterón, J. M.; Vicent, C.; Bosso, Penadés, S. J. Am. Chem. Soc. 1993, 115, 10066-10076. (c) Jiménez-Barbero, J.; Junquera, E.; Martín-Pastor, M.; Sharma, S.; Vicent, C.; Penadés, S. J. Am. Chem. Soc. 1995, 117, 11198-11204.
87. 5/w in Figure 8) actually results in no detectable increase in RU. This may be due to low SPR sensitivity of sodium phosphate in terms of mass (low molecular weight) as well as reflective index (high polarity).
88. 2.
89. Ready binding of concanavaline A, a glucose-binding (as well as mannose-binding) lectin, to the surface can be taken as another evidence for the saccharide-coated nature of the latter.