Carbohydrate recognition: Enantioselective spirobifluorene diphosphonate receptors

Tetrahedron Letters

Volumn 38, Issue 21, 1997, Pages 3675-3678

  Das, Goutam ^a   Hamilton, Andrew D ^a  

^a UNIVERSITY OF PITTSBURGH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BISPHOSPHONIC ACID DERIVATIVE; CARBOHYDRATE DERIVATIVE; FLUORENE DERIVATIVE; SPIRO COMPOUND;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; ENANTIOMER; IN VITRO STUDY; MODEL; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; RECEPTOR BINDING; STRUCTURE ACTIVITY RELATION;

EID: 0030902537     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00725-9     Document Type: Article

References (29)

1. For recent reviews see: Lemieux, R. U. Chem. Soc. Revs. 1989, 18, 347-374. Kobata, A. Acc. Chem. Res. 1993, 26, 319-324.
2. For recent reviews see: Lemieux, R. U. Chem. Soc. Revs. 1989, 18, 347-374. Kobata, A. Acc. Chem. Res. 1993, 26, 319-324.
3. Kikuchi, Y.; Tanaka, Y.; Sutarto, S.; Kobayashi, K.; Toi, H.; Aoyama, Y. J. Am. Chem. Soc. 1992, 114, 10302-10306. Bhattarai, K. M.; Bonar-Law, R. P.; Davis, A. P.; Murray, B. A. J. Chem. Soc., Chem. Commun. 1992, 752-754. Liu, R.; Still, W. C. Tetrahedron Lett. 1993, 34, 2573-2576. Savage, P. B.; Gellman, S. H. J. Am. Chem. Soc. 1993, 115, 10448-10449. Huang, C-Y.; Cabell, L. A.; Lynch, V. Anslyn, E. V. J. Am. Chem. Soc. 1994, 116, 2778-2792. Inouye, M.; Miyake, T.; Furusyo, M.; Nakazumi, H. J. Am. Chem. Soc. 1995, 117, 12416-12425.
4. Kikuchi, Y.; Tanaka, Y.; Sutarto, S.; Kobayashi, K.; Toi, H.; Aoyama, Y. J. Am. Chem. Soc. 1992, 114, 10302-10306. Bhattarai, K. M.; Bonar-Law, R. P.; Davis, A. P.; Murray, B. A. J. Chem. Soc., Chem. Commun. 1992, 752-754. Liu, R.; Still, W. C. Tetrahedron Lett. 1993, 34, 2573-2576. Savage, P. B.; Gellman, S. H. J. Am. Chem. Soc. 1993, 115, 10448-10449. Huang, C-Y.; Cabell, L. A.; Lynch, V. Anslyn, E. V. J. Am. Chem. Soc. 1994, 116, 2778-2792. Inouye, M.; Miyake, T.; Furusyo, M.; Nakazumi, H. J. Am. Chem. Soc. 1995, 117, 12416-12425.
5. Kikuchi, Y.; Tanaka, Y.; Sutarto, S.; Kobayashi, K.; Toi, H.; Aoyama, Y. J. Am. Chem. Soc. 1992, 114, 10302-10306. Bhattarai, K. M.; Bonar-Law, R. P.; Davis, A. P.; Murray, B. A. J. Chem. Soc., Chem. Commun. 1992, 752-754. Liu, R.; Still, W. C. Tetrahedron Lett. 1993, 34, 2573-2576. Savage, P. B.; Gellman, S. H. J. Am. Chem. Soc. 1993, 115, 10448-10449. Huang, C-Y.; Cabell, L. A.; Lynch, V. Anslyn, E. V. J. Am. Chem. Soc. 1994, 116, 2778-2792. Inouye, M.; Miyake, T.; Furusyo, M.; Nakazumi, H. J. Am. Chem. Soc. 1995, 117, 12416-12425.
6. Kikuchi, Y.; Tanaka, Y.; Sutarto, S.; Kobayashi, K.; Toi, H.; Aoyama, Y. J. Am. Chem. Soc. 1992, 114, 10302-10306. Bhattarai, K. M.; Bonar-Law, R. P.; Davis, A. P.; Murray, B. A. J. Chem. Soc., Chem. Commun. 1992, 752-754. Liu, R.; Still, W. C. Tetrahedron Lett. 1993, 34, 2573-2576. Savage, P. B.; Gellman, S. H. J. Am. Chem. Soc. 1993, 115, 10448-10449. Huang, C-Y.; Cabell, L. A.; Lynch, V. Anslyn, E. V. J. Am. Chem. Soc. 1994, 116, 2778-2792. Inouye, M.; Miyake, T.; Furusyo, M.; Nakazumi, H. J. Am. Chem. Soc. 1995, 117, 12416-12425.
7. Kikuchi, Y.; Tanaka, Y.; Sutarto, S.; Kobayashi, K.; Toi, H.; Aoyama, Y. J. Am. Chem. Soc. 1992, 114, 10302-10306. Bhattarai, K. M.; Bonar-Law, R. P.; Davis, A. P.; Murray, B. A. J. Chem. Soc., Chem. Commun. 1992, 752-754. Liu, R.; Still, W. C. Tetrahedron Lett. 1993, 34, 2573-2576. Savage, P. B.; Gellman, S. H. J. Am. Chem. Soc. 1993, 115, 10448-10449. Huang, C-Y.; Cabell, L. A.; Lynch, V. Anslyn, E. V. J. Am. Chem. Soc. 1994, 116, 2778-2792. Inouye, M.; Miyake, T.; Furusyo, M.; Nakazumi, H. J. Am. Chem. Soc. 1995, 117, 12416-12425.
8. Kikuchi, Y.; Tanaka, Y.; Sutarto, S.; Kobayashi, K.; Toi, H.; Aoyama, Y. J. Am. Chem. Soc. 1992, 114, 10302-10306. Bhattarai, K. M.; Bonar-Law, R. P.; Davis, A. P.; Murray, B. A. J. Chem. Soc., Chem. Commun. 1992, 752-754. Liu, R.; Still, W. C. Tetrahedron Lett. 1993, 34, 2573-2576. Savage, P. B.; Gellman, S. H. J. Am. Chem. Soc. 1993, 115, 10448-10449. Huang, C-Y.; Cabell, L. A.; Lynch, V. Anslyn, E. V. J. Am. Chem. Soc. 1994, 116, 2778-2792. Inouye, M.; Miyake, T.; Furusyo, M.; Nakazumi, H. J. Am. Chem. Soc. 1995, 117, 12416-12425.
9. Cuntze, J.; Owens, L.; Alcázar, V.; Seller, P.; Diederich, F. Helv. Chim. Acta 1995, 78, 367-390.
10. Beil, D. A.; Dfaz, S.; Lynch, M.; Anslyn, E. V. Tetrahedron Lett. 1995, 4155-4158.
11. Jimenéz-Barbero, J.; Junquerra, E.; Martín-Pastor, M.; Sharma, S.; Vicent, C.; Penadés, S. J. Am. Chem. Soc. 1995, 117, 11198-11204.
12. Tsukagoshi, K.; Shinkai, S. J. Org. Chem. 1991, 56, 4089-4091. James, T. D.; Samankumara Sandanayake, K. R. A.; Shinkai, S. Nature 1995, 374, 345-347.
13. Tsukagoshi, K.; Shinkai, S. J. Org. Chem. 1991, 56, 4089-4091. James, T. D.; Samankumara Sandanayake, K. R. A.; Shinkai, S. Nature 1995, 374, 345-347.
14. Quiocho, F. A. Pure & Appl. Chem. 1989, 61, 1293-1306.
15. Jorgensen, W. L.; Damm, W.; Frontera, A.; Lamb, M. L.; 1996, NATO ASI Ser. C. , Echegoyan, L.; Kaifer, A. E. Eds. Vol. 485, pp 115-126.
16. Das, G.; Hamilton, A. J. Am. Chem. Soc. 1994, 116, 11139-11140.
17. For a recent use of phosphate derivatives in sugar binding see: Anderson, S.; Neidlein, U.; Gramlich, V.; Diederich, F. Angew. Chem. Int. Ed. Engl. 1995, 34, 1596-1599.
18. Sanders, J. K. M.; Bonar-Law, R. P. J. Am. Chem. Soc. 1995, 117, 259-271.
19. Mizutani, T.; Murakami, T.; Matsumi, N.; Kurahashi, T.; Ogoshi, H. J. Chem. Soc., Chem. Commun. 1995, 1257-1258.
20. Hirao, T.; Masunaga, T.; Yamada, N. Ohshiro, Y.; Agawa, T. Bull. Chem. Soc. Jpn. 1982, 55, 909-913.
21. Maruyama, T. Taira, Z.; Horikawa, M.; Sato, Y.; Honjo, M. Tetrahedron Lett. 1983, 24, 2571-2574.
22. 13C NMR spectra and elemental analysis.
23. Alcazar, V.; Morán, J. R.; Diederich, F. Isr. J. Chem. 1992, 32, 69-77.
24. Using different versions of Hostest programs, Wilcox, C. S. Frontiers in Supramolecular Chemistry and Photochemistry; Schneider, H. J.; Durr, H., Eds.; VCH: Weinheim, 1990, p 123.
25. 31P NMR dilution studies and VPO experiments in acetonitrile in the range (5-25 mM).
26. Calculated (excluding counterions and solvent) using MM2*, MacroModel v. 3.5.
27. a's calculated this way reflect the average association constants.
28. E1,E2:glycoside]
29. (formula presented)