Molecular recognition of carbohydrates with acyclic pyridine-based receptors

Journal of Organic Chemistry

Volumn 69, Issue 22, 2004, Pages 7448-7462

  Mazik, Monika ^a   Radunz, Wolfgang ^b   Boese, Roland ^b  

^a TECHNICAL UNIVERSITY OF BRAUNSCHWEIG   (Germany)

^b UNIVERSITY OF DUISBURG ESSEN   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

BENZENE; NITROGEN;

BINDING PROPERTIES; MOLECULAR RECOGNITION;

CARBOHYDRATES;

1,3,5 TRIS[(4,6 DIMETHYLPYRIDIN 2 YL)AMINOMETHYL] 2,4,6 TRIETHYLBENZENE; 1,3,5 TRIS[(6 AMINOPYRIDIN 2 YL)AMINOMETHYL] 2,4,6 TRIETHYLBENZENE; 2,4,6 TRIETHYLBENZENE; 2,4,6 TRIMETHYLBENZENE; AMINOPYRIDINE; BENZENE DERIVATIVE; MONOSACCHARIDE; N DI(ETHOXYCARBONYLMETHYL) N',N'' BIS(4,6 DIMETHYLPYRIDIN 2 YL)BENZENE 1,3,5 TRICARBONAMIDE; N,N',N'' TRIS(6 ETHYLPYRIDIN 2 YL)BENZENE 1,3,5 TRICARBONAMIDE; PYRIDINE DERIVATIVE; RECEPTOR; UNCLASSIFIED DRUG;

ARTICLE; CARBOHYDRATE ANALYSIS; CARBON NUCLEAR MAGNETIC RESONANCE; CRYSTAL STRUCTURE; ENERGY; HYDROGEN BOND; MOLECULAR RECOGNITION; PROTON NUCLEAR MAGNETIC RESONANCE; RECEPTOR BINDING; SYNTHESIS; THERMODYNAMICS;

BINDING SITES; CARBOHYDRATES; MODELS, MOLECULAR; MOLECULAR CONFORMATION; MOLECULAR MIMICRY; MOLECULAR STRUCTURE; PYRIDINES; RECEPTORS, CELL SURFACE; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP; THERMODYNAMICS;

EID: 6344253005     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo048979k     Document Type: Article

References (42)

1. (a) Osborn, H.; Khan, T. Oligosaccharides. Their synthesis and biological roles; Oxford University Press: New York, 2000.
2. (b) Lis, H.; Sharon, N. Chem. Rev. 1998, 98, 637-674.
3. (a) Weiss, W. I.; Drickamer, K. Annu. Rev. Biochem. 1996, 65, 441-473.
4. (b) Quiocho, F. A. Pure. Appl. Chem. 1989, 61, 1293-1306.
5. (c) Lemieux, R. U. Chem. Soc. Rev. 1989, 78, 347-374.
6. (a) Davis, A. P.; Wareham, R. S. Angew. Chem., Int. Ed. 1999, 38, 2978-2996.
7. (b) Hartley, J. H.; James, T. D.; Ward, C. J. J. Chem. Soc., Perkin Trans. 1 2000, 3155-3184.
8. (c) For a recent review on boronic acid based receptors, see: James, T. D.; Shinkai, S. Top. Curr. Chem. 2002, 278, 159-200.
9. Some recent examples: (a) Velasco, T.; Lecollinet, G.; Ryan, T.; Davis, A. P. Org. Biol. Chem. 2004, 2, 645-647.
10. (b) Fang, J.-M.; Selvi, S.; Liao, J.-H.; Slanina, Z.; Chen, C.-T.; Chou, P.-T. J. Am. Chem. Soc. 2004, 2, 645-647.
11. (c) Welti, R.; Abel, Y.; Gramlich, V.; Diederich, F. Helv. Chim. Acta 2003, 86, 548-562.
12. (d) Welti, R.; Diederich, F. Helv. Chim. Acta 2003, 86, 494-503.
13. (e) Dukh, M.; Saman, D.; Lang, K.; Pouzar, V.; Cerny, I.; Drasar, P.; Král, V. Org. Biomol. Chem. 2003, 1, 3458-3463.
14. (f) Ishi-I, T.; Mateos-Timoneda, M. A.; Timmerman, P.; Crego-Calama, M.; Reinhoudt, D. N.; Shinkai, S. Angew. Chem., Int. Ed. 2003, 42, 2300-2305.
15. (g) Lecollinet, G.; Dominey, A. P.; Velasco, T.; Davis, A. P. Angew. Chem., Int. Ed. 2002, 41, 4093-4096.
16. (h) Tamaru, S.; Shinkai, S.; Khasanov, A. B.; Bell, T. W. Proc. Natl. Acad. Sci. U.S.A. 2002, 99, 4972-4976.
17. (i) Ladomenou, K.; Bonar-Law, R. P. Chem. Commun. 2002, 2108-2109.
18. (a) Mazik, M.; Bandmann, H.; Sicking, W. Angew. Chem., Int. Ed. 2000,39, 551-554.
19. (b) Mazik, M.; Sicking, W. Chem. Eur. J. 2001, 7, 664-670.
20. (c) Mazik, M.; Radunz, W.; Sicking, W. Org. Lett. 2002, 4, 4579-4582.
21. (d) Mazik, M.; Sicking, W. Tetrahedron Lett. 2004, 45, 3117-3121.
22. (a) Wilcox, C. S.; Glagovich, N. M. Program HOSTEST 5.6, University of Pittsburgh. This program is designed to fit data to different binding models, which include both "pure" binding models, taking into consideration the formation of only one type of complex in solution, and "mixed" binding models containing more than one type of complex in solution.
23. a2 corresponds to the 1:2 or 2:1 receptor/sugar association constant (for details see the text and Tables 1-3).
24. Schneider, H.-J.; Yatsimirsky, A. Principles and Methods in Supramolecular Chemistry; John Wiley & Sons: Chichester, 2000; p 148.
25. (b) Tsukube, H.; Furuta, H.; Odani, A.; Takeda, Y.; Kudo, Y.; Inoue, Y.; Liu, Y.; Sakamoto, H.; Kimura, K. In Comprehensive Supramolecular Chemistry; Atwood, J. L., Davis, J. E. D., MacNicol, D. D., Vogue, F., Eds.; Pergamon: Oxford, UK, 1996; Vol. 8, p 425.
26. Cuntze, J.; Owens, L.; Alcazar, V.; Seiler, P.; Diederich, F. Helv. Chim. Acta 1995, 78, 367-390.
27. Katritzky, A. R.; Pozharski, A. F. Handbook of Heterocyclic Chemistry; Pergamon: Amsterdam, The Netherlands, 2000; p 178.
28. Crystallographic data for the structures reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication nos. CCDC-229363 (2), 229364 (3), 235794 (4), 235792 (6), and 235793 (8).
29. For hydrogen-bonding motifs in the crystals of secondary diamides with 2-amino-6-methyl- and 2,6-diaminopyridine subunits, see: Mazik, M.; Bläser, D.; Boese, R. Tetrahedron 1999, 55, 12771-12781
30. Connors, K. A. In Comprehensive Supramolecular Chemistry; Atwood, J. L., Davis, J. E. D., MacNicol, D. D., Vögtle, F., Eds.; Pergamon: Oxford, U.K., 1996; Vol. 3, p 233.
31. For examples on the use of other systems based on the triethylbenzene frame, see: (a) Stack, T. D. P.; Hou, Z.; Raymond, K. N. J. Am. Chem. Soc. 1993, 115, 6466-6467.
32. (b) Niikura, K.; Metzger, A.; Anslyn, E. V. J. Am. Chem. Soc. 1998, 120, 8533-8534.
33. (c) Metzger, A.; Lynch, V. M.; Anslyn, E. V. J. Angew. Chem., Int. Ed. Engl. 1997, 36, 862-865.
34. (d) Kim S.-G.; Ahn, K. H. Chem. Eur. J. 2000, 6, 3399-3403.
35. (e) Chin, J.; Walsdorff C.; Stranix, B.; Oh, J.; Chung, H.-J.; Park, S.-M.; Kim, K. Angew. Chem., Int. Ed. 1999, 38, 2756-2759.
36. Cabell, L. A.; Best, M. D.; Lavigne, J. J.; Schneider, S. E.; Perreault, D. M.; Monahan, M.-K.; Anslyn, E. V. J. Chem. Soc., Perkin Trans. 2 2001, 315-323.
37. Chang, S.-K.; Van Engen, D.; Fan, E.; Hamilton, A. D. J. Am. Chem. Soc. 1991, 113, 7640-7645.
38. Podlaha, J.; Cisarova, I.; Alexander, D.; Holy, P.; Kraus, T.; Zavada, J. Collect. Czech. Chem. Commun. 2000, 65, 1587-1596.
39. (a) Jeong, K.-S.; Shin, K. H.; Kim, S.-H. Chem. Lett. 2002, 1166-1167.
40. (b) O'Leary, B. M.; Szabo, T.; Schalley, C. A.; Luezen, A.; Schaeer, M.; Rebek, J. J. Am. Chem. Soc. 2001, 123, 11519-11533.
41. Huang, C.-Y.; Cabell, L. A.; Anslyn, E. V. J. Am. Chem. Soc. 1994, 116, 2778-2792.
42. Van der Made, A. W.; van der Made, R. H. J. Org. Chem. 1993, 58, 1262-1263.