A hydrogen-bonding receptor that binds cationic monosaccharides with high affinity in methanol

Chemistry - A European Journal

Volumn 7, Issue 24, 2001, Pages 5270-5276

  Tamaru, Shun Ichi ^a   Yamamoto, Masashi ^a   Shinkai, Seiji ^a   Khasanov, Alisher B ^b   Bell, Thomas W ^b  

^a KYUSHU UNIVERSITY   (Japan)

^b UNIVERSITY OF NEVADA   (United States)

Author keywords

Carbohydrates; Chirality; Circular dichroism; Host guest systems; Hydrogen bonds

Indexed keywords

METHANOL; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; POSITIVE IONS; SOLVENTS;

MOLAR RATIO;

HYDROGEN BONDS;

AMMONIA; CARRIER PROTEIN; CATION; CELL SURFACE RECEPTOR; DICARBOXYLIC ACID DERIVATIVE; GALACTOSAMINE; GLUCOSAMINE; HYDROXYL GROUP; MANNOSAMINE; METHANOL; MONOSACCHARIDE; NITROGEN; RECEPTOR; SACCHARIDE BINDING PROTEINS; SACCHARIDE-BINDING PROTEINS;

AQUEOUS SOLUTION; ARTICLE; BINDING AFFINITY; BINDING COMPETITION; CHEMISTRY; CIRCULAR DICHROISM; COMPLEX FORMATION; CONCENTRATION RESPONSE; ELECTROCHEMISTRY; HYDROGEN BOND; METABOLISM; MOLECULAR DYNAMICS; MOLECULAR INTERACTION; MOLECULAR RECOGNITION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PROTON NUCLEAR MAGNETIC RESONANCE; RECEPTOR BINDING; SOLVATION; STRUCTURE ACTIVITY RELATION;

EID: 0035905424     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/1521-3765(20011217)7:24<5270::AID-CHEM5270>3.0.CO;2-H     Document Type: Article

References (75)

1. Some examples: a) J. Rebek, Jr., L. Marshall, R. Wolak, K. Parris, M. Killoran, B. Askew, D. Nemeth, N. Islam, J. Am. Chem. Soc. 1985, 107, 7476-7481;
2. b) A. D. Hamilton, D. van Engen, J. Am. Chem. Soc. 1987, 109, 5035-5036;
3. c) T. R. Kelly, M. P. Maguire, J. Am. Chem. Soc. 1987, 109, 6549-6551;
4. d) K. Kano, K. Yoshiyasu, S. Hashimoto, J. Chem. Soc. Chem. Commun. 1988, 801-802;
5. e) Y. Aoyama, Y. Tanaka, H. Toi, H. Ogoshi, J. Am. Chem. Soc. 1988, 110, 634-635;
6. f) T. W. Bell, J. Liu, J. Am. Chem. Soc. 1988, 110, 3673-3674;
7. g) M. C. Etter, T. W. Panunto, J. Am. Chem. Soc. 1988, 110, 5896-5897;
8. h) T. R. Kelly, C. Zhao, G. J. Bridger, J. Am. Chem. Soc. 1989, 111, 3744-3745;
9. i) Y. Tanaka, Y. Ubukata, Y. Aoyama, Chem. Lett. 1989, 1905-1908;
10. j) V. Hegde, P. Madhukar, J. D. Madura, R. P. Thummel, J. Am. Chem. Soc. 1990, 112, 4549-4550;
11. k) K. M. Neder, H. W. Whitlock, Jr., J. Am. Chem. Soc. 1990, 112, 9412-9414;
12. l) A. M. Kelly-Rowley, V. M. Lynch, E. V. Anslyn, J. Am. Chem. Soc. 1995, 117, 3438-3447;
13. m) A. Metzger, K. Gloe, H. Stephan, F. P. Schmidtchen, J. Org. Chem. 1996, 61, 2051-2055;
14. n) M. Martín, C. Raposo, M. Almaraz, M. Crego, C. Caballero, M. Grande, J. R. Moran, Angew. Chem. 1996, 108, 2512-2514;
15. Angew. Chem. Int. Ed. Engl. 1996, 35, 2386-2388;
16. o) T. Schrader, Chem. Eur. J. 1997, 3, 1537-1541.
17. Some reviews: a) J. Rebek, Jr., Angew. Chem. 1990, 102, 261-272
18. Angew. Chem. Int. Ed. Engl. 1990, 29, 245-255;
19. b) J. Rebek, Jr., Acc. Chem. Res. 1990, 23, 399-404;
20. c) H.-J. Schneider, Angew. Chem. 1991, 103, 1419-1439;
21. Angew. Chem. Int. Ed. Engl. 1991, 30 1417-1436;
22. d) C. Seel, A. Galán, J. de Mendoza, Top. Curr. Chem. 1995, 175, 101-132.
23. a) F. Garcia-Tellado, S. Goswami, S.-K. Chang, S. J. Geib, A. D. Hamilton, J. Am. Chem. Soc. 1990, 112, 7393-7394;
24. b) J. C. Adrian, Jr., C. S. Wilcox, J. Am. Chem. Soc. 1991, 113, 678-680;
25. c) E. Fan, S. A. Van Arman, S. Kincaid, A. D. Hamilton, J. Am. Chem. Soc. 1993, 115, 369-370;
26. d) T. W. Bell, Z. Hou, S. C. Zimmerman, P. A. Thiessen, Angew. Chem. 1995, 107, 2321-2324;
27. Angew. Chem. Int. Ed. Engl. 1995, 34, 2163-2165.
28. a) J. W. Becker, G. N. Reeke, Jr., J. L. Wang, B. A. Cunningham, G. M. Edelman, J. Biol. Chem. 1975, 250, 1513;
29. b) J. R. Helliwell, M. Helliwell, J. Chem. Soc. Chem. Commun. 1996, 1595-1602;
30. c) F. A. Quiocho, N. K. Vyas, Nature 1984, 310, 381-386.
31. a) R. P. Bonar-Law, A. P. Davis, B. A. Murray, Angew. Chem. 1990, 102, 1497-1499;
32. Angew. Chem. Int. Ed. Engl. 1990, 29, 1407-1408;
33. b) A. P. Davis, in Supramolecular Science: Where It Is and Where It Is Going (Eds.: R. Ungaro, E. Dalcanale), Kluwer, The Netherlands, 1999, p. 125, and references therein;
34. c) A. P. Davis, R. S. Wareham, Angew Chem. 1999, 111, 3160-3179;
35. Angew. Chem. Int. Ed. 1999, 38, 2978-2996, and references therein.
36. a) Y. Kikuchi, K. Kobayashi, Y. Aoyama, J. Am. Chem. Soc. 1992, 114, 1351-1358;
37. b) Y. Kikuchi, Y. Tanaka, S. Sutarto, K. Kobayashi, H. Toi, Y. Aoyama, J. Am. Chem. Soc. 1992, 114, 10302-10306;
38. c) K. Kobayashi, Y. Asakawa, Y. Kato, Y. Aoyama, J. Am. Chem. Soc. 1992, 114, 10307-10313.
39. a) C.-Y. Huang, L. A. Cabell, E. V. Anslyn, Tetrahedron Lett. 1990, 31, 7411-7414;
40. b) D. A. Bell, S. G. Díaz, V. M. Lynch, E. V. Anslyn, Tetrahedron Lett. 1995, 36, 4155-4158;
41. c) C.-Y. Huang, L. A. Cabell, E. V. Anslyn, J. Am. Chem. Soc. 1994, 116, 2778-2792.
42. a) M. Inouye, T. Miyake, M. Furusyo, H. Nakazumi, J. Am. Chem. Soc. 1995, 117, 12416-12425;
43. b) M. Inouye, K. Takahashi, H. Nakazumi, J. Am. Chem. Soc. 1999, 121, 341-345.
44. As an alternate method to bind saccharides in aqueous solution, the diol-boronic acid interaction is suggested, a) J. Yoon, A. W. Czarnik, J. Am. Chem. Soc. 1992, 114, 5874-5875;
45. b) T. D. James, K. R. A. S. Sandanayake, S. Shinkai, Angew. Chem. 1994, 106, 2287-2289;
46. Angew. Chem. Int. Ed. Engl. 1994, 33, 2207-2209;
47. c) T. D. James, K. R. A. S. Sandanayake, R. Iguchi, S. Shinkai, J. Am. Chem. Soc. 1995, 117, 8982-8987;
48. d) T. D. James, K. R. A. S. Sandanayake, S. Shinkai, Nature 1995, 374, 345-347;
49. e) D. P. Adhikiri, M. D. Heagy, Tetrahedron Lett. 1999, 40, 7893-7896.
50. a) U. Neidlein, F. Diederich, J. Chem. Soc. Chem. Commun. 1996, 1493-1494;
51. b) A. Bähr, B. Felber, K. Schneider, F. Diederich, Helv. Chim. Acta 2000, 83, 1346-1376.
52. V. Král, O. Rusin, F. P. Schmidtchen, Org. Lett. 2001, 3, 873-876.
53. T. W. Bell, Z. Hou, Angew. Chem. 1997, 109, 1601-1603;
54. Angew. Chem. Int. Ed. Engl. 1997, 36, 1536-1538.
55. T. W. Bell, N. M. Hext, A. B. Khasanov, Pure Appl. Chem. 1998, 70, 2371-2377, and references therein.
56. T. W. Bell, A. B. Khasanov, M. G. B. Drew, A. Filikov, T. L. James, Angew. Chem. 1999, 111, 2705-2709;
57. Angew. Chem. Int. Ed. Engl. 1999, 38, 2543-2547.
58. A. B. Khasanov, Ph. D. Thesis, University of Nevada, Reno (USA), 2000.
59. a) K. Kondo, Y. Shiomi, M. Saisho, T. Harada, S. Shinkai, Tetrahedron 1992, 48, 8239-8252;
60. b) Y. Shiomi, M. Saisho, K. Tsukagoshi, S. Shinkai, J. Chem. Soc. Perkin Trans. 1 1993, 2111-2117;
61. c) K. Nakashima, S. Shinkai, Chem. Lett. 1995, 443-444;
62. d) T. D. James, S. Shinkai, J. Chem. Soc. Chem. Commun. 1995, 1483-1485;
63. e) T. D. James, P. Linnane, S. Shinkai, J. Chem. Soc. Chem. Commun. 1996, 281-288;
64. f) M. Takeuchi, T. Mizuno, H. Shinmori, M. Nakashima, S. Shinkai, Tetrahedron 1996, 52, 1195-1204;
65. g) M. Takeuchi, S. Yoda, T. Imada, S. Shinkai, Tetrahedron 1997, 53, 8335-8348;
66. h) H. Kijima, M. Takeuchi, S. Shinkai, Chem. Lett. 1998, 781-782;
67. i) H. Shinmori, M. Takeuchi, S. Shinkai, J. Chem. Soc. Perkin Trans. 2 1998, 847-852;
68. j) M. Takeuchi, T. Imada, S. Shinkai, Bull. Chem. Soc. Jpn. 1998, 71, 1117-1123;
69. k) T. Mizuno, M. Takeuchi, I. Hamachi, K. Nakashima, S. Shinkai, J. Chem. Soc. Perkin Trans. 2 1998, 2281-2288;
70. l) M. Yamamoto, M. Takeuchi, F. Tani, Y. Naruta, S. Shinkai, J. Chem. Soc. Perkin Trans. 2 2000, 9-16;
71. m) T. Mizuno, M. Yamamoto, M. Takeuchi, S. Shinkai, Tetrahedron 2000, 56, 6193-6198.
72. S. Topiol, Chirality 1989, 1, 69-79.
73. S. Shinaki, K. Araki, O. Manabe, J. Am. Chem. Soc. 1988, 110, 7214-7215.
74. C. Rosini, C. Bertucci, C. Botteghi, R. Magarotto, Enantiomer 1998, 3, 365.
75. 1 values for 1·6 and 1·8. Under the conditions of the NMR experiment, even for the weakest complex (1·8), receptor 1 is more than 98% in the complexed form.