Expanding sapphyrin: Towards selective phosphate binding

Chemistry - A European Journal

Volumn 14, Issue 29, 2008, Pages 9065-9073

  Katayev, Evgeny A ^a,b   Boev, Nikolay V ^b   Myshkovskaya, Ekaterina ^a   Khrustalev, Victor N ^a   Ustynyuk, Yu A ^b  

^a A N NESMEYANOV INSTITUTE OF ORGANOELEMENT COMPOUNDS   (Russian Federation)

^b MOSCOW STATE UNIVERSITY   (Russian Federation)

Author keywords

Host guest systems; Phosphates receptor; Pyrroles; Receptors; Template synthesis

Indexed keywords

ACETIC ACID; AMIDES; BINDING ENERGY; CONDENSATION REACTIONS; HYDROCHLORIC ACID; HYDROGEN; INORGANIC ACIDS; INORGANIC COMPOUNDS; NEGATIVE IONS; NITROGEN COMPOUNDS; NUCLEAR MAGNETIC RESONANCE; POTASSIUM COMPOUNDS; SYNTHESIS (CHEMICAL); VOLUMETRIC ANALYSIS; X RAY DIFFRACTION ANALYSIS;

BINDING PROPERTIES; BIPYRROLE; DIHYDROGEN PHOSPHATES; EFFICIENT SYNTHESES; HIGH AFFINITIES; HOST-GUEST SYSTEMS; HYDROGEN SULFATES; IMINE BONDS; MACROCYCLIC; MACROCYCLIZATION REACTIONS; PHOSPHATE BINDINGS; PYRROLE RINGS; PYRROLES; RECEPTORS; SAPPHYRIN; SINGLECRYSTAL X-RAY DIFFRACTION ANALYSES; STABILITY CONSTANTS; TEMPLATE SYNTHESIS; TEMPLATED; TEMPLATED SYNTHESIS; TETRABUTYLAMMONIUM ACETATES; TETRABUTYLAMMONIUM CHLORIDES; TETRABUTYLAMMONIUM SALTS; WATER SOLUTIONS;

TITRATION;

ANION; PHOSPHATE; PORPHYRIN; SAPPHYRIN;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

ANIONS; CRYSTALLOGRAPHY, X-RAY; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, MOLECULAR; MOLECULAR STRUCTURE; PHOSPHATES; PORPHYRINS;

EID: 55049105702     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200800860     Document Type: Article

References (52)

1. J.-M. Lehn, Chem. Soc. Rev. 2007, 36, 151-160.
2. J. L. Sessler, P. A. Gale, W.-S. Cho, Anion Receptor Chemistry, Royal Society of Chemistry, Cambridge, 2006.
3. K. Severin, Top. Organomet. Chem. 2006, 17, 123-142.
4. S. Stadlbauer, A. Riechers, A. Späth, B. König, Chem. Eur. J. 2007, 13, 2536-2541.
5. C. Schmuck, Angew. Chem. 2007, 119, 5932-5935;
6. Angew. Chem. Int. Ed. 2007, 46, 5830-5833;
7. M. J. Hannon, Chem. Soc. Rev. 2007, 36, 280-295.
8. A. K. H. Hirsch, F. R. Fischer, F. Diederich, Angew. Chem. 2007, 119, 342-357;
9. Angew. Chem. Int. Ed. 2007, 46, 338-352.
10. E. A. Katayev, Y. A. Ustynyuk, X L. Sessler, Coord. Chem. Rev. 2006, 250, 3004-3037.
11. S. O. Kang, M. A. Hossain, K. Bowman-James, Coord. Chem. Rev. 2006, 250, 3038-3052.
12. S. Kubik, C. Reyheller, S. Stüwe, J. Inclusion Phenom. Macrocyclic Chem. 2005, 52, 137-187.
13. M. D. Lankshear, P, D. Beer, Acc. Chem. Res. 2007, 40, 657-668.
14. M. D. Lankshear, P.D. Beer, Coord. Chem. Rev. 2006, 250, 3142-3160.
15. P. A. Gale, R. Quesada, Coord. Chem. Rev. 2006, 250, 3219-3244.
16. T.J. Wedge, M. F. Hawthorne, Coord. Chem. Rev. 2003, 240, 111-128.
17. M. Bru, I. Alfonso, M. I. Burguete, S. V. Luis, Angew. Chem. 2006, 118, 6301-6305;
18. Angew. Chem. Int. Ed. 2006, 45, 6155-6159.
19. S. L. Tobey, B. D. Jones, E. V. Anslyn, 3. Am. Chem. Soc. 2003, 125, 4026-4027.
20. M. Allevi, M. Bonizzoni, L. Fabbrizzi, Chem. Eur. J. 2007, 13, 3787-3795.
21. P. T. Gunning, Org. Biomol. Chem. 2005, 3, 3877-3879.
22. M. S. Han, D. H. Kim, Angew. Chem. 2002, 114, 3963-3965;
23. Angew. Chem. Int. Ed. 2002, 41, 3809-3811.
24. V. Král, H. Furuta, K. Shreder, V. Lynch, J. L. Sessler, J. Am. Chem. Soc. 1996, 118, 1595-1607.
25. S. K. Kim, N. J. Singh, S. J. Kim, H. G. Kim, J. K. Kim, J. W. Lee, K. S. Kim, J. Yoon, Org. Lett. 2003, 5, 2083-2086.
26. J. Y. Kwon, N. J. Singh, H. N. Kim, S. K. Kim, K. S. Kim, J. Yoon, J. Am. Chem. Soc. 2004, 126, 8892-8893.
27. P. Schiessl, F. P. Schmidtchen, J. Org. Chem. 1994, 59, 509-511.
28. P. S. Lakshminarayanan, I. Ravikumar, E. Suresh, P. Ghosh, Chem. Commun. 2007, 5214-5216.
29. A. N. Leung, D. A. Degenhardt, P. Bühlmann, Tetrahedron 2008, 64, 2530-2536.
30. J.-H. Liao, C.-T. Chen, J.-M. Fang, Org. Lett. 2002, 4, 561-564.
31. I. E. D. Vega, S. Camiolo, P. A. Gale, M. B. Hursthouse, M. E. Light, Chem. Commun. 2003, 1686-1687.
32. I. E. D. Vega, P. A. Gale, M. B. Hursthouse, M. E. Light, Org. Biomol. Chem. 2004, 2, 2935-2941.
33. A. Andrievsky, F. Ahuis, J. L. Sessler, F. Vögtle, D. Gudat, M. Moini, J. Am. Chem. Soc. 1998, 120, 9712-9713.
34. J. L. Sessler, E. Katayev, G. D. Pantos, Y. A. Ustynyuk, Chem. Commun. 2004, 1276-1277.
35. E. A. Katayev, G. D. Pantos, M. D. Reshetova, V. N. Khrustalev, V. M. Lynch, Y. A. Ustynyuk, J. L. Sessler, Angew. Chem. 2005, 117, 7552-7556;
36. Angew. Chem. Int. Ed. 2005, 44, 7386-7390.
37. E. A. Katayev, J. L. Sessler, V. N. Khrustalev, Y. A. Ustynyuk, J. Org. Chem. 2007, 72, 7244-7252.
38. E. A. Katayev, N. V. Boev, V. N. Khrustalev, Y. A. Uslynyuk, I. G. Tananaev, J. L. Sessler, J. Org. Chem. 2007, 72, 2886-2896.
39. B. L. Iverson, K. Shreder, V. Král, P. Sansom, V. Lynch, J. L. Sessler, J. Am. Chem. Soc. 1996, 118, 1608-1616.
40. E. A. Katayev, E. N. Myshkovskaya, N. V. Boev, V. N. Khrustalev, Supramol Chem. 2008, DOI: 10.1080/10610270701561342.
41. J. L. Sessler, J. M. Davis, Acc. Chem. Res. 2001, 34, 989-997.
42. D. Seidel, V. Lynch, J. L. Sessler, Angew. Chem. 2002, 114, 1480-1483;
43. Angew. Chem. Int. Ed. 2002, 41, 1422-1425.
44. P. Gans, A. Sabatini, A. Vacca, Talanta 1996, 43, 1739-1753.
45. S. O. Kang, R. A. Begum, K. Bowman-James, Angew. Chem. 2006, 118, 8048-8061;
46. Angew. Chem. Int. Ed. 2006, 45, 7882-7894.
47. K. A. Connors, Binding constants, Wiley, New York, 1987.
48. B. J. Whitlock, H. W. Whitlock, J. Am. Chem. Soc. 1990, 112, 3910-3915.
49. N. V. Boev, Y. A. Ustynyuk, Russ. J. Org. Chem. 2007, 43, 297-304.
50. Bruker SAINTPlus, Data Reduction and Correction Program, v. 6.01, Bruker AXS, Madison, WI, 1998.
51. PLATON, A Multipurpose Crystallographic Tool, A. L. Spek, Utrecht University, The Netherlands, 1998.
52. SHELXTL, v. 5.10, Structure Determination Software Suite, G. M. Sheldrick, Bruker AXS, Madison, WI, 1998.