High α/β-Anomer Selectivity in Molecular Recognition of Carbohydrates by Artificial Receptors

Organic Letters

Volumn 4, Issue 26, 2002, Pages 4579-4582

  Mazik, Monika ^a   Radunz, Wolfgang ^a   Sicking, Willi ^a  

^a UNIVERSITY OF DUISBURG ESSEN   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

CARBOHYDRATE; CELL SURFACE RECEPTOR; GLUCORECEPTOR; GLUCOSE; LIGAND; PYRIDINE; PYRIDINE DERIVATIVE;

ARTICLE; BINDING SITE; CARBOHYDRATE METABOLISM; CHEMICAL STRUCTURE; CHEMISTRY; HYDROGEN BOND; METABOLISM; MOLECULAR MIMICRY; STEREOISOMERISM; STRUCTURE ACTIVITY RELATION;

BINDING SITES; CARBOHYDRATE METABOLISM; CARBOHYDRATES; GLUCOSE; HYDROGEN BONDING; LIGANDS; MODELS, MOLECULAR; MOLECULAR MIMICRY; PYRIDINES; RECEPTORS, CELL SURFACE; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 0442264163     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0201759     Document Type: Article

References (30)

1. For a recent review on carbohydrate recognition through noncovalent interactions, see: Davis, A. P.; Wareham, R. S. Angew. Chem., Int. Ed. 1999, 38, 2978-2996.
2. For recent reports on hydrogen-bonding receptors for carbohydrates, see: (a) Ryan, T. J.; Lecollinet, G.; Velasco, T.; Davis, A. P. Proc. Natl. Acad. Sci. U.S.A. 2002, 99, 4863-4866 and references therein. (b) Rusin, O.; Lang, K.; Kral, V. Chem. Eur. J. 2002, 8, 655-663. (c) Droz, A. S.; Neidlein, U.; Anderson, S.; Seiler, P.; Diederich, F. Helv. Chim. Acta 2001, 84, 2243-2289. (d) Löwik, D. W. P. M.; Lowe, C. R. Eur. J. Org. Chem. 2001, 2825-2839. (e) Benito, J. M.; Gomez-Garcia, M.; Jimenez Blanco, J. L.; Ortiz Mellet, C.; Garcia Fernandez, J. M. J. Org. Chem. 2001, 66, 1366-1372. (f) Tamaru, S.-i.; Yamamoto, M.; Shinkai, S.; Khasanow, A. B.; Bell, T. W. Chem. Eur. J. 2001, 7, 5270-5276. (g) Kim, H. J.; Kim, Y. H.; Hong, J. I. Tetrahedron Lett. 2001, 42, 5049-5052. (h) Bitta, J.; Kubik, S. Org. Lett. 2001, 3, 2637-2640. (i) Mazik, M.; Sicking, W. Chem. Eur. J. 2001, 7, 664-670. (j) Mazik, M.; Bandmann, H.; Sicking, W. Angew. Chem., Int. Ed. 2000, 39, 551-554.
3. For recent reports on hydrogen-bonding receptors for carbohydrates, see: (a) Ryan, T. J.; Lecollinet, G.; Velasco, T.; Davis, A. P. Proc. Natl. Acad. Sci. U.S.A. 2002, 99, 4863-4866 and references therein. (b) Rusin, O.; Lang, K.; Kral, V. Chem. Eur. J. 2002, 8, 655-663. (c) Droz, A. S.; Neidlein, U.; Anderson, S.; Seiler, P.; Diederich, F. Helv. Chim. Acta 2001, 84, 2243-2289. (d) Löwik, D. W. P. M.; Lowe, C. R. Eur. J. Org. Chem. 2001, 2825-2839. (e) Benito, J. M.; Gomez-Garcia, M.; Jimenez Blanco, J. L.; Ortiz Mellet, C.; Garcia Fernandez, J. M. J. Org. Chem. 2001, 66, 1366-1372. (f) Tamaru, S.-i.; Yamamoto, M.; Shinkai, S.; Khasanow, A. B.; Bell, T. W. Chem. Eur. J. 2001, 7, 5270-5276. (g) Kim, H. J.; Kim, Y. H.; Hong, J. I. Tetrahedron Lett. 2001, 42, 5049-5052. (h) Bitta, J.; Kubik, S. Org. Lett. 2001, 3, 2637-2640. (i) Mazik, M.; Sicking, W. Chem. Eur. J. 2001, 7, 664-670. (j) Mazik, M.; Bandmann, H.; Sicking, W. Angew. Chem., Int. Ed. 2000, 39, 551-554.
4. For recent reports on hydrogen-bonding receptors for carbohydrates, see: (a) Ryan, T. J.; Lecollinet, G.; Velasco, T.; Davis, A. P. Proc. Natl. Acad. Sci. U.S.A. 2002, 99, 4863-4866 and references therein. (b) Rusin, O.; Lang, K.; Kral, V. Chem. Eur. J. 2002, 8, 655-663. (c) Droz, A. S.; Neidlein, U.; Anderson, S.; Seiler, P.; Diederich, F. Helv. Chim. Acta 2001, 84, 2243-2289. (d) Löwik, D. W. P. M.; Lowe, C. R. Eur. J. Org. Chem. 2001, 2825-2839. (e) Benito, J. M.; Gomez-Garcia, M.; Jimenez Blanco, J. L.; Ortiz Mellet, C.; Garcia Fernandez, J. M. J. Org. Chem. 2001, 66, 1366-1372. (f) Tamaru, S.-i.; Yamamoto, M.; Shinkai, S.; Khasanow, A. B.; Bell, T. W. Chem. Eur. J. 2001, 7, 5270-5276. (g) Kim, H. J.; Kim, Y. H.; Hong, J. I. Tetrahedron Lett. 2001, 42, 5049-5052. (h) Bitta, J.; Kubik, S. Org. Lett. 2001, 3, 2637-2640. (i) Mazik, M.; Sicking, W. Chem. Eur. J. 2001, 7, 664-670. (j) Mazik, M.; Bandmann, H.; Sicking, W. Angew. Chem., Int. Ed. 2000, 39, 551-554.
5. For recent reports on hydrogen-bonding receptors for carbohydrates, see: (a) Ryan, T. J.; Lecollinet, G.; Velasco, T.; Davis, A. P. Proc. Natl. Acad. Sci. U.S.A. 2002, 99, 4863-4866 and references therein. (b) Rusin, O.; Lang, K.; Kral, V. Chem. Eur. J. 2002, 8, 655-663. (c) Droz, A. S.; Neidlein, U.; Anderson, S.; Seiler, P.; Diederich, F. Helv. Chim. Acta 2001, 84, 2243-2289. (d) Löwik, D. W. P. M.; Lowe, C. R. Eur. J. Org. Chem. 2001, 2825-2839. (e) Benito, J. M.; Gomez-Garcia, M.; Jimenez Blanco, J. L.; Ortiz Mellet, C.; Garcia Fernandez, J. M. J. Org. Chem. 2001, 66, 1366-1372. (f) Tamaru, S.-i.; Yamamoto, M.; Shinkai, S.; Khasanow, A. B.; Bell, T. W. Chem. Eur. J. 2001, 7, 5270-5276. (g) Kim, H. J.; Kim, Y. H.; Hong, J. I. Tetrahedron Lett. 2001, 42, 5049-5052. (h) Bitta, J.; Kubik, S. Org. Lett. 2001, 3, 2637-2640. (i) Mazik, M.; Sicking, W. Chem. Eur. J. 2001, 7, 664-670. (j) Mazik, M.; Bandmann, H.; Sicking, W. Angew. Chem., Int. Ed. 2000, 39, 551-554.
6. For recent reports on hydrogen-bonding receptors for carbohydrates, see: (a) Ryan, T. J.; Lecollinet, G.; Velasco, T.; Davis, A. P. Proc. Natl. Acad. Sci. U.S.A. 2002, 99, 4863-4866 and references therein. (b) Rusin, O.; Lang, K.; Kral, V. Chem. Eur. J. 2002, 8, 655-663. (c) Droz, A. S.; Neidlein, U.; Anderson, S.; Seiler, P.; Diederich, F. Helv. Chim. Acta 2001, 84, 2243-2289. (d) Löwik, D. W. P. M.; Lowe, C. R. Eur. J. Org. Chem. 2001, 2825-2839. (e) Benito, J. M.; Gomez-Garcia, M.; Jimenez Blanco, J. L.; Ortiz Mellet, C.; Garcia Fernandez, J. M. J. Org. Chem. 2001, 66, 1366-1372. (f) Tamaru, S.-i.; Yamamoto, M.; Shinkai, S.; Khasanow, A. B.; Bell, T. W. Chem. Eur. J. 2001, 7, 5270-5276. (g) Kim, H. J.; Kim, Y. H.; Hong, J. I. Tetrahedron Lett. 2001, 42, 5049-5052. (h) Bitta, J.; Kubik, S. Org. Lett. 2001, 3, 2637-2640. (i) Mazik, M.; Sicking, W. Chem. Eur. J. 2001, 7, 664-670. (j) Mazik, M.; Bandmann, H.; Sicking, W. Angew. Chem., Int. Ed. 2000, 39, 551-554.
7. For recent reports on hydrogen-bonding receptors for carbohydrates, see: (a) Ryan, T. J.; Lecollinet, G.; Velasco, T.; Davis, A. P. Proc. Natl. Acad. Sci. U.S.A. 2002, 99, 4863-4866 and references therein. (b) Rusin, O.; Lang, K.; Kral, V. Chem. Eur. J. 2002, 8, 655-663. (c) Droz, A. S.; Neidlein, U.; Anderson, S.; Seiler, P.; Diederich, F. Helv. Chim. Acta 2001, 84, 2243-2289. (d) Löwik, D. W. P. M.; Lowe, C. R. Eur. J. Org. Chem. 2001, 2825-2839. (e) Benito, J. M.; Gomez-Garcia, M.; Jimenez Blanco, J. L.; Ortiz Mellet, C.; Garcia Fernandez, J. M. J. Org. Chem. 2001, 66, 1366-1372. (f) Tamaru, S.-i.; Yamamoto, M.; Shinkai, S.; Khasanow, A. B.; Bell, T. W. Chem. Eur. J. 2001, 7, 5270-5276. (g) Kim, H. J.; Kim, Y. H.; Hong, J. I. Tetrahedron Lett. 2001, 42, 5049-5052. (h) Bitta, J.; Kubik, S. Org. Lett. 2001, 3, 2637-2640. (i) Mazik, M.; Sicking, W. Chem. Eur. J. 2001, 7, 664-670. (j) Mazik, M.; Bandmann, H.; Sicking, W. Angew. Chem., Int. Ed. 2000, 39, 551-554.
8. For recent reports on hydrogen-bonding receptors for carbohydrates, see: (a) Ryan, T. J.; Lecollinet, G.; Velasco, T.; Davis, A. P. Proc. Natl. Acad. Sci. U.S.A. 2002, 99, 4863-4866 and references therein. (b) Rusin, O.; Lang, K.; Kral, V. Chem. Eur. J. 2002, 8, 655-663. (c) Droz, A. S.; Neidlein, U.; Anderson, S.; Seiler, P.; Diederich, F. Helv. Chim. Acta 2001, 84, 2243-2289. (d) Löwik, D. W. P. M.; Lowe, C. R. Eur. J. Org. Chem. 2001, 2825-2839. (e) Benito, J. M.; Gomez-Garcia, M.; Jimenez Blanco, J. L.; Ortiz Mellet, C.; Garcia Fernandez, J. M. J. Org. Chem. 2001, 66, 1366-1372. (f) Tamaru, S.-i.; Yamamoto, M.; Shinkai, S.; Khasanow, A. B.; Bell, T. W. Chem. Eur. J. 2001, 7, 5270-5276. (g) Kim, H. J.; Kim, Y. H.; Hong, J. I. Tetrahedron Lett. 2001, 42, 5049-5052. (h) Bitta, J.; Kubik, S. Org. Lett. 2001, 3, 2637-2640. (i) Mazik, M.; Sicking, W. Chem. Eur. J. 2001, 7, 664-670. (j) Mazik, M.; Bandmann, H.; Sicking, W. Angew. Chem., Int. Ed. 2000, 39, 551-554.
9. For recent reports on hydrogen-bonding receptors for carbohydrates, see: (a) Ryan, T. J.; Lecollinet, G.; Velasco, T.; Davis, A. P. Proc. Natl. Acad. Sci. U.S.A. 2002, 99, 4863-4866 and references therein. (b) Rusin, O.; Lang, K.; Kral, V. Chem. Eur. J. 2002, 8, 655-663. (c) Droz, A. S.; Neidlein, U.; Anderson, S.; Seiler, P.; Diederich, F. Helv. Chim. Acta 2001, 84, 2243-2289. (d) Löwik, D. W. P. M.; Lowe, C. R. Eur. J. Org. Chem. 2001, 2825-2839. (e) Benito, J. M.; Gomez-Garcia, M.; Jimenez Blanco, J. L.; Ortiz Mellet, C.; Garcia Fernandez, J. M. J. Org. Chem. 2001, 66, 1366-1372. (f) Tamaru, S.-i.; Yamamoto, M.; Shinkai, S.; Khasanow, A. B.; Bell, T. W. Chem. Eur. J. 2001, 7, 5270-5276. (g) Kim, H. J.; Kim, Y. H.; Hong, J. I. Tetrahedron Lett. 2001, 42, 5049-5052. (h) Bitta, J.; Kubik, S. Org. Lett. 2001, 3, 2637-2640. (i) Mazik, M.; Sicking, W. Chem. Eur. J. 2001, 7, 664-670. (j) Mazik, M.; Bandmann, H.; Sicking, W. Angew. Chem., Int. Ed. 2000, 39, 551-554.
10. For recent reports on hydrogen-bonding receptors for carbohydrates, see: (a) Ryan, T. J.; Lecollinet, G.; Velasco, T.; Davis, A. P. Proc. Natl. Acad. Sci. U.S.A. 2002, 99, 4863-4866 and references therein. (b) Rusin, O.; Lang, K.; Kral, V. Chem. Eur. J. 2002, 8, 655-663. (c) Droz, A. S.; Neidlein, U.; Anderson, S.; Seiler, P.; Diederich, F. Helv. Chim. Acta 2001, 84, 2243-2289. (d) Löwik, D. W. P. M.; Lowe, C. R. Eur. J. Org. Chem. 2001, 2825-2839. (e) Benito, J. M.; Gomez-Garcia, M.; Jimenez Blanco, J. L.; Ortiz Mellet, C.; Garcia Fernandez, J. M. J. Org. Chem. 2001, 66, 1366-1372. (f) Tamaru, S.-i.; Yamamoto, M.; Shinkai, S.; Khasanow, A. B.; Bell, T. W. Chem. Eur. J. 2001, 7, 5270-5276. (g) Kim, H. J.; Kim, Y. H.; Hong, J. I. Tetrahedron Lett. 2001, 42, 5049-5052. (h) Bitta, J.; Kubik, S. Org. Lett. 2001, 3, 2637-2640. (i) Mazik, M.; Sicking, W. Chem. Eur. J. 2001, 7, 664-670. (j) Mazik, M.; Bandmann, H.; Sicking, W. Angew. Chem., Int. Ed. 2000, 39, 551-554.
11. For recent reports on hydrogen-bonding receptors for carbohydrates, see: (a) Ryan, T. J.; Lecollinet, G.; Velasco, T.; Davis, A. P. Proc. Natl. Acad. Sci. U.S.A. 2002, 99, 4863-4866 and references therein. (b) Rusin, O.; Lang, K.; Kral, V. Chem. Eur. J. 2002, 8, 655-663. (c) Droz, A. S.; Neidlein, U.; Anderson, S.; Seiler, P.; Diederich, F. Helv. Chim. Acta 2001, 84, 2243-2289. (d) Löwik, D. W. P. M.; Lowe, C. R. Eur. J. Org. Chem. 2001, 2825-2839. (e) Benito, J. M.; Gomez-Garcia, M.; Jimenez Blanco, J. L.; Ortiz Mellet, C.; Garcia Fernandez, J. M. J. Org. Chem. 2001, 66, 1366-1372. (f) Tamaru, S.-i.; Yamamoto, M.; Shinkai, S.; Khasanow, A. B.; Bell, T. W. Chem. Eur. J. 2001, 7, 5270-5276. (g) Kim, H. J.; Kim, Y. H.; Hong, J. I. Tetrahedron Lett. 2001, 42, 5049-5052. (h) Bitta, J.; Kubik, S. Org. Lett. 2001, 3, 2637-2640. (i) Mazik, M.; Sicking, W. Chem. Eur. J. 2001, 7, 664-670. (j) Mazik, M.; Bandmann, H.; Sicking, W. Angew. Chem., Int. Ed. 2000, 39, 551-554.
12. For a recent review on boronic acid based receptors, using covalent interactions for sugar binding, see: James, T. D.; Shinkai, S. Top. Curr. Chem. 2002, 218, 159-200.
13. (a) Quiocho, F. A. Pure. Appl. Chem. 1989, 61, 1293-1306.
14. (b) Weiss, W. I.; Drickamer, K. Annu. Rev. Biochem. 1996, 65, 441-473.
15. (c) Lis, H.; Sharon, N. Chem. Rev. 1998, 98, 637-674.
16. (d) Elgavish, S.; Shaanan, B. Trends Biochem. Sci. 1998, 22, 462-467.
17. van der Made, A. W.; van der Made, R. H. J. Org. Chem. 1993, 58, 1262-1263.
18. a of substituted pyridines is generally greater for α- and γ-than for β-amino or -methyl groups: Katritzky, A. R.; Pozharski, A. F. Handbook of Heterocyclic Chemistry; Pergamon: Amsterdam, The Netherlands, 2000; p 178.
19. For examples on the use of the effect of increased basicity of pyridine moieties in other hydrogen-bonded systems, see: (a) Inouye, M.; Miyake, T.; Furusyo, M.; Nakazumi, H. J. Org. Chem. 1999, 64, 8170-8176. (b) Tecilla, P.; Dixon, R. P.; Slobodkin, G.; Alavi, D. S.; Waldeck, D. H.; Hamilton, A. D. J. Am. Chem. Soc. 1990, 112, 9408-9410.
20. For examples on the use of the effect of increased basicity of pyridine moieties in other hydrogen-bonded systems, see: (a) Inouye, M.; Miyake, T.; Furusyo, M.; Nakazumi, H. J. Org. Chem. 1999, 64, 8170-8176. (b) Tecilla, P.; Dixon, R. P.; Slobodkin, G.; Alavi, D. S.; Waldeck, D. H.; Hamilton, A. D. J. Am. Chem. Soc. 1990, 112, 9408-9410.
21. 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.
22. For examples on the use of the mole ratio method, see: (a) 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. Vögtle, F., Eds.; Pergamon: Oxford, UK, 1996; Vol. 8, pp 425-482. (b) Liu, M. T. H.; Bonneau, R. J. Am. Chem. Soc. 1990, 112, 3915-3919.
23. For examples on the use of the mole ratio method, see: (a) 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. Vögtle, F., Eds.; Pergamon: Oxford, UK, 1996; Vol. 8, pp 425-482. (b) Liu, M. T. H.; Bonneau, R. J. Am. Chem. Soc. 1990, 112, 3915-3919.
24. 9: 483.2859. Found: 483.2867.
25. A similar effect was previously observed for other systems. See: (a) Bonar-Law, R. P.; Sanders, J. K. M. J. Am. Chem. Soc. 1995, 117, 259-271. (b) Mizutani, T.; Kurahashi, T.; Murakami, T.; Matsumi, N.; Ogoshi, H. J. Am. Chem. Soc. 1997, 119, 8991-9001.
26. A similar effect was previously observed for other systems. See: (a) Bonar-Law, R. P.; Sanders, J. K. M. J. Am. Chem. Soc. 1995, 117, 259-271. (b) Mizutani, T.; Kurahashi, T.; Murakami, T.; Matsumi, N.; Ogoshi, H. J. Am. Chem. Soc. 1997, 119, 8991-9001.
27. Jeffrey, G. A.; Saenger, W. A. Hydrogen Bonding in Biological Structures;, Springer-Verlag: Berlin, Germany, 1994.
28. 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. (b) Niikura, K.; Metzger, A.; Anslyn, E. V. J. Am. Chem. Soc. 1998, 120, 8533-8534. (c) Kim, S.-G.; Ann, K. H. Chem. Eur. J. 2000, 6, 3399-3403.
29. 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. (b) Niikura, K.; Metzger, A.; Anslyn, E. V. J. Am. Chem. Soc. 1998, 120, 8533-8534. (c) Kim, S.-G.; Ann, K. H. Chem. Eur. J. 2000, 6, 3399-3403.
30. 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. (b) Niikura, K.; Metzger, A.; Anslyn, E. V. J. Am. Chem. Soc. 1998, 120, 8533-8534. (c) Kim, S.-G.; Ann, K. H. Chem. Eur. J. 2000, 6, 3399-3403.