Upper rim guanidinocalix[4]arenes as artificial phosphodiesterases

Journal of Organic Chemistry

Volumn 77, Issue 7, 2012, Pages 3381-3389

  Baldini, Laura ^a   Cacciapaglia, Roberta ^b   Casnati, Alessandro ^a   Mandolini, Luigi ^b   Salvio, Riccardo ^b   Sansone, Francesco ^a   Ungaro, Rocco ^a  

^a UNIVERSITY OF PARMA   (Italy)

^b SAPIENZA UNIVERSITY OF ROME   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

ACIDITY MEASUREMENT; ARENE DERIVATIVES; CALIX[4]ARENE DERIVATIVES; CALIX[4]ARENES; CATALYTIC RATES; CONE CONFORMATIONS; FUNCTIONALIZED; GENERAL BASE; GUANIDINIUM; MODEL COMPOUND; MOLECULAR FRAMEWORKS; MONOFUNCTIONAL; P-NITROPHENYL PHOSPHATE; PH DEPENDENCE; PHOSPHODIESTERASES; PROTONATED; STERIC INTERFERENCE;

ENZYME INHIBITION; RNA;

PROTONATION;

CALIXARENE; GUANIDINE DERIVATIVE; GUANIDINOCALIX[4]ARENE; PHOSPHODIESTERASE; PROTON; RNA; UNCLASSIFIED DRUG;

ACIDITY; ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; PH; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; SYNTHESIS;

CALIXARENES; CATALYSIS; GUANIDINE; HYDROGEN-ION CONCENTRATION; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; PHENOLS; PHOSPHORIC DIESTER HYDROLASES; RNA; STEREOISOMERISM;

EID: 84859598362     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo300193y     Document Type: Article

References (67)

1. Brinker, U. H., Mieusset, J.-L., Eds. Molecular Encapsulation-Organic Reactions in Constrained Systems; John Wiley & Sons, Ltd.: New York, 2010.
2. van Leeuwen, P. W. N. M., Ed. Supramolecular Catalysis; Wiley-VCH Verlag GmbH & Co. KgaA: Weinheim, Germany, 2008.
3. Breslow, R. A. E. I. Artificial Enzymes; Breslow, R., Ed.; Wiley-VCH Verlag GmbH & Co. KGaA: Weinheim, Germany, 2005.
4. Molenveld, P.; Engbersen, J. F. J.; Reinhoudt, D. N. Chem. Soc. Rev. 2000, 29, 75-86
5. Morrow, J. Curr. Opin. Chem. Biol. 2004, 8, 192-200
6. Mancin, F.; Scrimin, P.; Tecilla, P.; Tonellato, U. Chem. Commun. 2005, 2540-2548
7. Niittymäki, T.; Lönnberg, H. Org. Biomol. Chem. 2006, 4, 15-25
8. Scarso, A.; Zaupa, G.; Houillon, F. B.; Prins, L. J.; Scrimin, P. J. Org. Chem. 2007, 72, 376-385
9. Cacciapaglia, R.; Casnati, A.; Mandolini, L.; Peracchi, A.; Reinhoudt, D. N.; Salvio, R.; Sartori, A.; Ungaro, R. J. Am. Chem. Soc. 2007, 129, 12512-12520
10. Tseng, T.-S. A.; Burstyn, J. N. Chem. Commun. 2008, 6209-6211
11. Bonomi, R.; Selvestrel, F.; Lombardo, V.; Sissi, C.; Polizzi, S.; Mancin, F.; Tonellato, U.; Scrimin, P. J. Am. Chem. Soc. 2008, 130, 15744-15745
12. Bazzicalupi, C.; Bencini, A.; Bonaccini, C.; Giorgi, C.; Gratteri, P.; Moro, S.; Palumbo, M.; Simionato, A.; Sgrignani, J.; Sissi, C.; Valtancoli, B. Inorg. Chem. 2008, 47, 5473-5484
13. Nwe, K.; Andolina, C. M.; Morrow, J. R. J. Am. Chem. Soc. 2008, 130, 14861-14871
14. Katada, H.; Komiyama, M. ChemBioChem 2009, 10, 1279-1288
15. Lindgren, N. J. V.; Lars Geiger, J. R.; Schmuck, C.; Baltzer, L. Angew. Chem., Int. Ed. 2009, 48, 6722-6725
16. Thomas, J. M.; Yoon, J.-K.; Perrin, D. M. J. Am. Chem. Soc. 2009, 131, 5648-5658
17. Hollenstein, M.; Hipolito, C. J.; Lam, C. H.; Perrin, D. M. ChemBioChem 2009, 10, 1988-1992
18. Mohamed, M. F.; Brown, R. S. J. Org. Chem. 2010, 75, 8471-8477
19. Lönnberg, H. Org. Biomol Chem. 2011, 9, 1687-1703
20. Wolfenden, R. Chem. Rev. 2006, 106, 3379-3396
21. Demesmaeker, A.; Haner, R.; Martin, P.; Moser, H. E. Acc. Chem. Res. 1995, 28, 366-374
22. Trawick, B. N.; Daniher, A. T.; Bashkin, J. K. Chem. Rev. 1998, 98, 939-960
23. Dospil, G.; Schatz, J. Tetrahedron Lett. 2001, 42, 7837-7840
24. Cacciapaglia, R.; Casnati, A.; Di Stefano, S.; Mandolini, L.; Paolemili, D.; Reinhoudt, D. N.; Sartori, A.; Ungaro, R. Chem.-Eur. J. 2004, 10, 4436-4442
25. Cacciapaglia, R.; Casnati, A.; Mandolini, L.; Reinhoudt, D. N.; Salvio, R.; Sartori, A.; Ungaro, R. J. Org. Chem. 2005, 70, 624-630
26. Cacciapaglia, R.; Casnati, A.; Mandolini, L.; Reinhoudt, D. N.; Salvio, R.; Sartori, A.; Ungaro, R. J. Org. Chem. 2005, 70, 5398-5402
27. Cacciapaglia, R.; Casnati, A.; Mandolini, L.; Reinhoudt, D. N.; Salvio, R.; Sartori, A.; Ungaro, R. J. Am. Chem. Soc. 2006, 128, 12322-12330
28. Cacciapaglia, R.; Casnati, A.; Mandolini, L.; Reinhoudt, D. N.; Salvio, R.; Sartori, A.; Ungaro, R. Inorg. Chim. Acta 2007, 360, 981-986
29. Cacciapaglia, R.; Di Stefano, S.; Mandolini, L. Molecular Encapsulation, Organic Reaction in Constrained Systems; John Wiley & Sons: New York, 2010; Chapter 8.
30. Cotton, F. A.; Hazen, E. E., Jr.; Legg, M. J. Proc. Natl. Acad. Sci. U.S.A. 1979, 76, 2551-2555
31. Kurz, K.; Göbel, M. W. Helv. Chim. Acta 1996, 79, 1967-1979
32. Cuevas, F.; Di Stefano, S.; Magrans, J. O.; Prados, P.; Mandolini, L.; de Mendoza, J. Chem.-Eur. J. 2000, 6, 3228-3234
33. Scheffer, U.; Strick, A.; Ludwig, V.; Peter, S.; Kalden, E.; Göbel, M. W. J. Am. Chem. Soc. 2005, 127, 2211-2217
34. Gnaccarini, C.; Peter, S.; Scheffer, U.; Vonhoff, S.; Klussmann, S.; Göbel, M. W. J. Am. Chem. Soc. 2006, 128, 8063-8067
35. Corona-Martinez, D. O.; Taran, O.; Yatsimirsky, A. K. Org. Biomol. Chem. 2010, 8, 873-880
36. Sheng, X.; Lu, X.; Y., C.; Lu, G.; Zhang, J.; Shao, Y.; Liu, F.; Xu, Q. Chem.-Eur. J. 2007, 13, 9703-9712
37. Ait-Haddou, H.; Sumaoka, J.; Wiskur, S. L.; Folmer-Andersen, J. F.; Anslyn, E. V. Angew. Chem., Int. Ed. 2002, 41, 4014-4016
38. Suh, J.; Moon, S.-J. Inorg. Chem. 2001, 40, 4890-4895
39. Salvio, R.; Cacciapaglia, R.; Mandolini, L. J. Org. Chem. 2011, 76, 5438-5443
40. Muche, M. S.; Göbel, M. W. Angew. Chem., Int. Ed. 1996, 35, 2126-2129
41. Smith, J.; Ariga, K.; Anslyn, E. V. J. Am. Chem. Soc. 1993, 115, 362-364
42. Piatek, A. M.; Gray, M.; Anslyn, E. V. J. Am. Chem. Soc. 2004, 126, 9878-9879
43. Best, M. D.; Tobey, S. L.; Anslyn, E. V. Coord. Chem. Rev. 2003, 240, 3-15 and references therein.
44. Tobey, S. L.; Anslyn, E. V. J. Am. Chem. Soc. 2003, 125, 14807-14815
45. Sansone, F.; Dudic, M.; Donofrio, G.; Rivetti, C.; Baldini, L.; Casnati, A.; Cellai, S.; Ungaro, R. J. Am. Chem. Soc. 2006, 128, 14528-14536
46. Bagnacani, V.; Sansone, F.; Donofrio, G.; Baldini, L.; Casnati, A.; Ungaro, R. Org. Lett. 2008, 10, 3953-3956
47. Corbellini, F.; Mulder, A.; Sartori, A.; Ludden, M. J. W.; Casnati, A.; Ungaro, R.; Huskens, J.; Crego-Calama, M.; Reinhoudt, D. N. J. Am. Chem. Soc. 2004, 126, 17050-17058
48. Kopaczynska, M.; Wang, T. Y.; Schulz, A.; Dudic, M.; Casnati, A.; Sansone, F.; Ungaro, R.; Fuhrhop, J. H. Langmuir 2005, 21, 8460-8465
49. Dudic, M.; Colombo, A.; Sansone, F.; Casnati, A.; Donofrio, G.; Ungaro, R. Tetrahedron 2004, 60, 11613-11618
50. Verboom, W.; Durie, A.; Egberink, R. J. M.; Asfari, Z.; Reinhoudt, D. N. J. Org. Chem. 1992, 57, 1313-1316
51. van Loon, J. D.; Heida, J. F.; Verboom, W.; Reinhoudt, D. N. Recl. Trav. Chim. Pays-Bas 1992, 111, 353-359
52. Sartori, A.; Casnati, A.; Mandolini, L.; Sansone, F.; Reinhoudt, D. N.; Ungaro, R. Tetrahedron 2003, 59, 5539-5544
53. Baldini, L.; Melegari, M.; Bagnacani, V.; Casnati, A.; Dalcanale, E.; Sansone, F.; Ungaro, R. J. Org. Chem. 2011, 76, 3720-3732
54. Georgieva, M. Anal. Chim. Acta 1977, 90, 83-89
55. Wróbel, R.; Chmurzyński, L. Anal. Chim. Acta 2000, 405, 303-308
56. Taran, O.; Yatsimirsky, A. K. Chem. Commun. 2004, 1228-1229
57. Gomez-Tagle, P.; Vargas-Zuniga, I.; Taran, O.; Yatsimirsky, A. K. J. Org. Chem. 2006, 71, 9713-9722
58. Sanchez-Lombardo, I.; Yatsimirsky, A. K. Inorg. Chem. 2008, 47, 2514-2525
59. Ariga, K.; Anslyn, E. V. J. Org. Chem. 1992, 57, 417-420
60. Kneeland, D. M.; Ariga, K.; Lynch, V. M.; Huang, C. Y.; Anslyn, E. V. J. Am. Chem. Soc. 1993, 115, 10042-10055
61. Chu, F. Y.; Flatt, L. S.; Anslyn, E. V. J. Am. Chem. Soc. 1994, 116, 4194-4204
62. Kreevoy, M. M.; Baughman, E. H. J. Phys. Chem. 1974, 78, 421-423
63. Pawlak, Z.; Bates, R. G. J. Solution Chem. 1975, 4, 817-829
64. Brown, D. M.; Usher, D. A. J. Chem. Soc. 1965, 6558-6564
65. Yang, X.; McBranch, D.; Swanson, B.; Li, D. Angew. Chem., Int. Ed. 1996, 35, 538-540
66. Gans, P.; Sabatini, A.; Vacca, A. Talanta 1996, 43, 1739-1753
67. Alderighi, L.; Gans, P.; Ienco, A.; Peters, D.; Sabatini, A.; Vacca, A. Coord. Chem. Rev. 1999, 184, 311-318