Guanidine-guanidinium cooperation in bifunctional artificial phosphodiesterases based on diphenylmethane spacers; Gem -dialkyl effect on catalytic efficiency

Journal of Organic Chemistry

Volumn 78, Issue 14, 2013, Pages 7259-7263

  Salvio, Riccardo ^a   Mandolini, Luigi ^a   Savelli, Claudia ^a  

^a SAPIENZA UNIVERSITY OF ROME   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMISTRY;

ACTIVATION PARAMETER; CATALYTIC EFFICIENCIES; DFT CALCULATION; DIPHENYLMETHANE; GEM-DIALKYL EFFECT; METHYLENE GROUPS; PHOSPHODIESTERASES; ROTATIONAL BARRIERS;

ORGANIC COMPOUNDS;

BENZENE DERIVATIVE; DIPHENYLMETHANE DERIVATIVE; GUANIDINE DERIVATIVE; PHOSPHODIESTERASE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; COVALENT BOND; KINETICS; TRANSESTERIFICATION;

EID: 84880520036     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo401085z     Document Type: Article

References (44)

1. Supramolecular Catalysis; van Leeuwen, P. W. N. M., Ed.; Wiley-VCH Verlag GmbH & Co. KgaA: Weinheim, Germany, 2008.
2. Kumagai, N.; Shibasaki, M. Catal. Sci. Technol. 2013, 3, 41
3. Molenveld, P.; Engbersen, J. F. J.; Reinhoudt, D. N. Chem. Soc. Rev. 2000, 29, 75
4. Morrow, J. R.; Iranzo, O. Curr. Opin. Chem. Biol. 2004, 8, 192
5. Cacciapaglia, R.; Casnati, A.; Mandolini, L.; Reinhoudt, D. N.; Salvio, R.; Sartori, A.; Ungaro, R. J. Org. Chem. 2005, 70, 624
6. Mancin, F.; Scrimin, P.; Tecilla, P.; Tonellato, U. Chem. Commun. 2005, 2540
7. Niittymäki, T.; Lönnberg, H. Org. Biomol. Chem. 2006, 4, 15
8. Cacciapaglia, R.; Casnati, A.; Mandolini, L.; Reinhoudt, D. N.; Salvio, R.; Sartori, A.; Ungaro, R. J. Am. Chem. Soc. 2006, 128, 12322
9. Scarso, A.; Zaupa, G.; Houillon, F. B.; Prins, L. J.; Scrimin, P. J. Org. Chem. 2007, 72, 376
10. Cacciapaglia, R.; Casnati, A.; Mandolini, L.; Peracchi, A.; Reinhoudt, D. N.; Salvio, R.; Sartori, A.; Ungaro, R. J. Am. Chem. Soc. 2007, 129, 12512
11. Tseng, T.-S. A.; Burstyn, J. N. Chem. Commun. 2008, 6209
12. Bonomi, R.; Selvestrel, F.; Lombardo, V.; Sissi, C.; Polizzi, S.; Mancin, F.; Tonellato, U.; Scrimin, P. J. Am. Chem. Soc. 2008, 130, 15744
13. 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
14. Nwe, K.; Andolina, C. M.; Morrow, J. R. J. Am. Chem. Soc. 2008, 130, 14861
15. Katada, H.; Komiyama, M. ChemBioChem 2009, 10, 1279
16. Mohamed, M. F.; Brown, R. S. J. Org. Chem. 2010, 75, 8471
17. Salvio, R.; Cacciapaglia, R.; Mandolini, L. J. Org. Chem. 2011, 76, 5438
18. Piatek, A. M.; Gray, M.; Anslyn, E. V. J. Am. Chem. Soc. 2004, 126, 9878
19. Scheffer, U.; Strick, A.; Ludwig, V.; Peter, S.; Kalden, E.; Göbel, M. W. J. Am. Chem. Soc. 2005, 127, 2211
20. Gnaccarini, C.; Peter, S.; Scheffer, U.; Vonhoff, S.; Klussmann, S.; Göbel, M. W. J. Am. Chem. Soc. 2006, 128, 8063
21. Lindgren, N. J. V.; Lars Geiger, J. R.; Schmuck, C.; Baltzer, L. Angew. Chem., Int. Ed. 2009, 48, 6722
22. Thomas, J. M.; Yoon, J.-K.; Perrin, D. M. J. Am. Chem. Soc. 2009, 131, 5648
23. Hollenstein, M.; Hipolito, C. J.; Lam, C. H.; Perrin, D. M. ChemBioChem 2009, 10, 1988
24. Lönnberg, H. Org. Biomol. Chem. 2011, 9, 1687
25. Corona-Martinez, D. O.; Taran, O.; Yatsimirsky, A. K. Org. Biomol. Chem. 2010, 8, 873
26. Baldini, L.; Cacciapaglia, R.; Casnati, A.; Mandolini, L.; Salvio, R.; Sansone, F.; Ungaro, R. J. Org. Chem. 2012, 77, 3381
27. Eliel, E. L.; Wilen, S. H. Stereochemistry of Organic Compounds; John Wiley & Sons, Inc.: New York, 1994; Chapter 11.
28. Jung, M. E.; Piizzi, G. Chem. Rev. 2005, 105, 1735
29. Yi, M. H.; Huang, W.; Jin, M. Y.; Choi, K.-Y. Macromolecules 1997, 30, 5606
30. Yi, M. H.; Huang, W.; Lee, B. J.; Choi, K.-Y. J. Polym. Sci., Part A: Polym. Chem. 1999, 37, 3449
31. Salvio, R.; Casnati, A.; Mandolini, L.; Sansone, F.; Ungaro, R. Org. Biomol. Chem. 2012, 10, 8941
32. Kreevoy, M. M.; Baughman, E. H. J. Phys. Chem. 1974, 78, 421
33. Beesley, R. M.; Ingold, C. K.; Thorpe, J. F. J. Chem. Soc., Trans. 1915, 107, 1080
34. Hammond, G. S. In Steric Effects in Organic Chemistry; Newman, M. S., Ed.; John Wiley & Sons: New York, 1956.
35. Allinger, N. L.; Zalkow, V. J. Org. Chem. 1960, 25, 701
36. ⧧ arising from release of some frozen solvent molecules on going from reactants to transition state. For a thorough discussion of reactions between ions, see: Frost, A. A.; Pearson, R. G. Kinetics and Mechanism, 2 nd ed.; John Wiley & Sons: New York, 1961; Chapter 7.
37. Frisch, M. J.; GAUSSIAN-03, revision D.02; Gaussian, Inc.: Pittsburgh, PA, 2003.
38. Cacciapaglia, R.; Di Stefano, S.; Mandolini, L. Acc. Chem. Res. 2004, 37, 113
39. Brown, D. M.; Usher, D. A. J. Chem. Soc. 1965, 6558
40. Dardonville, C.; Goya, P.; Rozas, I.; Alsasua, A.; Martín, I.; Borrego, M. J. Bioorg. Med. Chem. 2000, 8, 1567
41. Alderighi, L.; Gans, P.; Ienco, A.; Peters, D.; Sabatini, A.; Vacca, A. Coord. Chem. Rev. 1999, 184, 311
42. Pitzer, K. S.; Gwinn, W. D. J. Chem. Phys. 1942, 10, 428
43. Pitzer, K. S. J. Chem. Phys. 1946, 14, 239
44. Kilpatrick, J. E.; Pitzer, K. S. J. Chem. Phys. 1949, 17, 1064