Recognition of anionic carbohydrates by an artificial receptor in water

Organic Letters

Volumn 7, Issue 16, 2005, Pages 3517-3520

  Schmuck, Carsten ^a   Schwegmann, Michael ^a  

^a UNIVERSITY OF WÜRZBURG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

CARBOHYDRATE; WATER;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; COMPARATIVE STUDY; CONFORMATION; ELECTROCHEMISTRY; HYDROGEN BOND; NUCLEAR MAGNETIC RESONANCE;

CARBOHYDRATE CONFORMATION; CARBOHYDRATES; ELECTROCHEMISTRY; HYDROGEN BONDING; MOLECULAR STRUCTURE; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; WATER;

EID: 23944444258     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol051230r     Document Type: Article

References (53)

1. Reviews on chemosensors: (a) Martinez-Manez, R.; Sancenon, F. Chem. Rev. 2003, 103, 4419-4476.
2. (b) Czarnik, A W.; Yoon, J. Persp. Supramol. Chem. 1999, 4, 177-191.
3. (c) De Silva, A. P.; Gunaratne, H. Q. N.; Gunnlaugsson, T.; Huxley, A. J. M.; McCoy, C. P.; Rademacher, J. T.; Rice, Terence E. Chem. Rev. 1997, 97, 1515-1566.
4. (e) Czarnik, A. W. Chem. Biol. 1995, 2, 423-428.
5. For recent review articles on artificial peptide receptors, see: (a) Peczuh, M. W.; Hamilton, A. D. Chem. Rev. 2000, 100, 2479-2494.
6. (b) Schneider, H.-J. Adv. Supramol. Chem. 2000, 6, 185-216.
7. For selected recent examples, see: (a) Schmuck, C.; Geiger, L. J. Am. Chem. Soc. 2004, 126, 8898-8899.
8. (b) Schmuck, C.; Heil, M. ChemBioChem 2003, 4, 1232-1238.
9. (c) Rensing, S.; Schrader, T. Org. Lett. 2002, 4, 2161-2164.
10. (d) Jensen, K.; Braxmeier, T. M.; Demarcus, M.; Frey, J. G.; Kilburn, J. D. Chem. - Eur. J. 2002, 8, 1300-1309.
11. (e) Xuo, R.; Greiveldinger, G.; Marenus, L. E.; Cooper, A.; Ellman, J. A. J. Am. Chem. Soc. 1999, 121, 4898-4899.
12. For reviews, see: (a) Davis, A. P.; Wareham, R. S. Angew. Chem. 1999, 111, 3160-3179;
13. Angew. Chem., Int. Ed. 1999, 38, 2978-2996.
14. (b) Striegler, S. Curr. Org. Chem. 2003, 7, 81-102.
15. For recent examples, see: (a) Lee, J.-D.; Greene, N. T.; Rushton, G. T.; Shimizu, K. D.; Hong, J.-I. Org. Lett. 2005, 7, 963-966.
16. (b) Mazik, M.; Sicking, W. Tetrahedron Lett. 2004, 45, 3117-3121.
17. (c) Mazik, M.; Radunz, W.; Boese, R. J. Org. Chem. 2004, 69, 7448-7462.
18. (d) Ishi-i, T.; Mateos-Timoneda, M. A.; Timmerman, P.; Crego-Calama, M.; Reinhoudt, D. N.; Shinkai, S. Angew. Chem. 2003, 115, 2402-2407;
19. Angew. Chem., Int. Ed. 2003, 42, 2300-2305.
20. (e) Segura, M.; Bricoli, B.; Casnati, A.; Munoz, E. M.; Sansone, F.; Ungaro, R. Vicent, C. J. Org. Chem. 2003, 68, 6296-6303.
21. (f) Wada, K.; Mizutani, T.; Kitagawa, S. J. Org. Chem. 2003, 68, 5123-5131.
22. (g) Welti, R.; Diederich, F. Helv. Chim. Acta 2003, 86, 494-503.
23. (h) Mazik, M.; Radunz, W.; Sicking, W. Org. Lett. 2002, 4, 4579-4582.
24. (i) Kim, Y. H.; Hong, J. I. Angew. Chem. 2002, 114, 3071-3074;
25. Angew. Chem., Int. Ed. 2002, 41, 2947-2950.
26. (j) Ladomenou, K.; Bonar-Law, R. P. Chem. Commun. 2002, 2108-2109.
27. (k) Liao, J. H.; Chen, C. T.; Chou, H. C.; Cheng, C. C.; Chou, P. T.; Fang, J. M.; Slanina, Z.; Chow, T, J. Org. Lett. 2002, 4, 3107-3110.
28. (l) Bitta, J.; Kubik, S. Org. Lett. 2001, 3, 2637-2640.
29. (m) Tamaru, S.; Yamamoto, M.; Shinkai, S.; Khasanov, A. B.; Bell, T. W. Chem. - Eur. J. 2001, 7, 5270-5276.
30. (a) Klein, E.; Crump, M. P.; Davis, A. P. Angew. Chem., Int. Ed. 2005, 44, 298-302.
31. (b) Hubbard, R. D.; Horner, S. R.; Miller, B. L. J. Am. Chem. Soc. 2001, 123, 5810-5811.
32. (c) Kral, V.; Rusin, O.; Schmidtchen, F. P. Org. Lett. 2001, 3, 873-876.
33. (d) Sugimoto, N.; Miyoshi, D.; Zou, J. Chem. Commun. 2000, 2295-2296.
34. For a review, see: James, T. D.; Sandanayake, K. R. A. S.; Shinkai, S. Angew. Chem., Int. Ed. Engl. 1996, 35, 1910-1922.
35. Anderson, S.; Neidlein, U.; Gramlich, V.; Diederich, F. Angew. Chem. 1995, 107, 1722-1726;
36. Angew. Chem., Int. Ed. Engl. 1995, 34, 1596-1600.
37. Aoyama, Y.; Tanaka, Y.; Toi, H.; Ogoshi, H. J. Am. Chem. Soc. 1988, 110, 634-635.
38. Schmuck, C.; Schwegmann, M. J. Am. Chem. Soc. 2005, 127, 3373-3379.
39. (a) Zhong, Z.; Anslyn, E. V. J. Am. Chem. Soc. 2002, 124, 9014-9015.
40. (b) Wiskur, S. L.; Ait-Haddou, H.; Lavinge, J. J.; Anslyn, E. V. Acc. Chem. Res. 2001, 34, 963-972.
41. (a) Wilcox, C. S. In Frontiers in Supramolecular Chemistry and Photochemistry; Schneider, H. J., Dürr, H., Eds.; VCH: Weinheim, 1990; pp 123-144.
42. (b) Hirose, K. J. Incl. Phenom. Macro. Chem. 2001, 39, 193-209.
43. (c) Connors, K. A. Binding Constants; Wiley: New York, 1987.
44. (d) Fielding, L. Tetrahedron 2000, 56, 6151-6170.
45. Mohamadi, F.; Richards, N. G. J.; Guida, W. C.; Liskamp, R.; Lipton, M.; Caufiled, C.; Chang, G.; Hendrickson, T.; Still, W. C. J. Comput. Chem. 1990, 11, 440-467
46. Binding by all three cationic arms is also supported by the fact that at pH = 7.4, where the receptor is only monoprotonated, no complexation of the uronic acids could be detected.
47. This conformer is, however, calculated (Amber* force field, water GB/SA solvation model) to be only 2.4 kJ/mol less stable than the ground state conformation of 3.
48. (a) Schug, K. A.; Lindner, W. Chem. Rev. 2005, 105, 67-113.
49. (b) Best, M. D.; Tobey, S. L.; Anslyn, E. V. Coord. Chem. Rev. 2003, 240, 3-15.
50. (a) Jin, L.; Abrahams, J. P.; Skinner, R.; Petitou, M.; Pike, R. N.; Carell, R. W. Proc. Natl. Acad. Sci. U.S.A. 1997, 94, 14683-14688.
51. (b) Sharma, A.; Askari, J. A.; Humphries, M. J.; Jones, E. Y.; Stuart, D. I. EMBO 1999, 18, 6, 1468-1479.
52. (c) Simanek, E. E.; McGarvey, G. J.; Jablonowski, J. A.; Wong, C.-H. Chem. Rev. 1998, 98, 833-862.
53. (d) Wong, C.-H. Acc. Chem. Res. 1999, 32, 376-385.