Water-catalyzed excited-state proton-transfer reactions in 7-azaindole and its analogues

Journal of Physical Chemistry B

Volumn 119, Issue 6, 2015, Pages 2302-2309

  Wu, Yu Sin ^a   Huang, Huai Ching ^a   Shen, Jiun Yi ^a   Tseng, Huan Wei ^a   Ho, Jr Wei ^a   Chen, You Hua ^a   Chou, Pi Tai ^a  

^a NATIONAL TAIWAN UNIVERSITY   (Taiwan)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; ELECTRONS; FLUORESCENCE SPECTROSCOPY; GROUND STATE; PROTON TRANSFER; PROTONATION; SYNTHESIS (CHEMICAL);

CATIONIC FORMS; ELECTRON WITHDRAWING GROUP; ELECTRON-DONATING; ELECTRON-DONATING SUBSTITUENTS; ELECTRONWITHDRAWING; EXCITED-STATE PROTON TRANSFER; PEAK WAVELENGTH; SYSTEMATIC STUDY;

EXCITED STATES;

EID: 84922802239     PISSN: 15206106     EISSN: 15205207     Source Type: Journal    
DOI: 10.1021/jp506136v     Document Type: Article

References (31)

1. Taylor, C. A.; Elbayoumi, M. A.; Kasha, M. Excited-State Two-Proton Tautomerism in Hydrogen-Bonded N-Heterococlic Base Pairs Proc. Natl. Acad. Sci. U.S.A. 1969, 63, 253-260
2. Watson, J. D.; Crick, F. H. C. Molecular Structure of Nucleic Acids - A Structure for Deoxyribose Nucleic Acid Nature 1953, 171, 737-738
3. Doudney, C. O.; Rinaldi, C. N. Evidence That Ultraviolet Light-Induced DNA-Replication Death of recA Bacteria Is Prevented by Protein-Synthesis in Repair-Proficient Bacteria Mutat. Res. 1989, 217, 33-38
4. Ingham, K. C.; Elbayoumi, M. A. Photoinduced Double Proton-Transfer in a Model Hydrogen-Bonded Base Pair. Effects of Temperature and Deuterium Substitution J. Am. Chem. Soc. 1974, 96, 1674-1682
5. Moog, R. S.; Maroncelli, M. 7-Azaindole in Alcohols: Solvation Dynamics and Proton Transfer J. Phys. Chem. 1991, 95, 10359-10369
6. Chen, Y.; Rich, R. L.; Gai, F.; Petrich, J. W. Fluorescent Species of 7-Azaindole and 7-Azatryptophan in Water J. Phys. Chem. 1993, 97, 1770-1780
7. McMorrow, D.; Aartsma, T. J. Solvent-Mediated Proton-Transfer the Roles of Solvent Structure and Dynamics on the Excited-State Tautomerization of 7-Azaindole/Alcohol Complexes Chem. Phys. Lett. 1986, 125, 581-585
8. Takeuchi, S.; Tahara, T. Observation of Dimer Excited-State Dynamics in the Double Proton Transfer Reaction of 7-Azaindole by Femtosecond Fluorescence Up-Conversion Chem. Phys. Lett. 1997, 277, 340-346
9. Takeuchi, S.; Tahara, T. The Answer to Concerted versus Step-Wise Controversy for the Double Proton Transfer Mechanism of 7-Azaindole Dimer in Solution Proc. Natl. Acad. Sci. U.S.A. 2007, 104, 5285-5290
10. Chapman, C. F.; Maroncelli, M. Excited-State Tautomerization of 7-Azaindole in Water J. Phys. Chem. 1992, 96, 8430-8441
11. Negrerie, M.; Bellefeuille, S. M.; Whitham, S.; Petrich, J. W.; Thornburg, R. W. Novel Noninvasive in Situ Probe of Protein-Structure and Dynamics J. Am. Chem. Soc. 1990, 112, 7419-7421
12. Negrerie, M.; Gai, F.; Bellefeuille, S. M.; Petrich, J. W. Photophysics of a Novel Optical Probe: 7-Azaindole J. Phys. Chem. 1991, 95, 8663-3670
13. Gai, F.; Chen, Y.; Petrich, J. W. Nonradiative Pathways of 7-Azaindole in Water J. Am. Chem. Soc. 1992, 114, 8343-8345
14. Abel, R.; Salam, N. K.; Shelley, J.; Farid, R.; Friesner, R. A.; Sherman, W. Contribution of Explicit Solvent Effects to the Binding Affinity of Small-Molecule Inhibitors in Blood Coagulation Factor Serine Proteases ChemMedChem 2011, 6, 1049-1066
15. Robinson, D. D.; Sherman, W.; Farid, R. Understanding Kinase Selectivity through Energetic Analysis of Binding Site Waters ChemMedChem 2010, 5, 618-627
16. Beuming, T.; Che, Y.; Abel, R.; Kim, B.; Shanmugasundaram, V.; Sherman, W. Thermodynamic Analysis of Water Molecules at the Surface of Proteins and Applications to Binding Site Prediction and Characterization Proteins 2012, 80, 871-883
17. Wang, L.; Berne, B. J.; Friesner, R. A. Ligand Binding to Protein-Binding Pockets with Wet and Dry Regions Proc. Natl. Acad. Sci. U.S.A. 2011, 108, 1326-1330
18. Shen, J. Y.; Chao, W. C.; Liu, C.; Pan, H. A.; Yang, H. C.; Chen, C. L.; Lan, Y. K.; Lin, L. J.; Wang, J. S.; Lu, J. F. Probing Water Micro-Solvation in Proteins by Water Catalysed Proton-Transfer Tautomerism Nat. Commun. 2013, 4, 2611-2617
19. Chou, P. T.; Chen, Y. C.; Yu, W. S.; Chou, Y. H.; Wei, C. Y.; Cheng, Y. M. Excited-State Intramolecular Proton Transfer in 10-Hydroxybenzo[h]quinoline J. Phys. Chem. A 2001, 105, 1731-1740
20. Chou, P. T.; Pu, S. C.; Cheng, Y. M.; Yu, W. S.; Yu, Y. C.; Hung, F. T.; Hu, W. P. Femtosecond Dynamics on Excited-State Proton Charge-Transfer Reaction in 4′- N, N -Diethylamino-3-hydroxyflavone. The Role of Dipolar Vectors in Constructing a Rational Mechanism J. Phys. Chem. A 2005, 109, 3777-3787
21. Avouris, P.; Yang, L. L.; Elbayoumi, M. A. Excited-State Interactions of 7-Azaindole with Alcohol and Water Photochem. Photobiol. 1976, 24, 211-216
22. Chou, P. T.; Martinez, M. L.; Cooper, W. C.; McMorrow, D.; Collins, S. T.; Kasha, M. Monohydrate Catalysis of Excited-State Double-Proton Transfer in 7-Azaindole J. Phys. Chem. 1992, 96, 5203-5205
23. Robison, M. M.; Robison, B. L. 7-Azaindole. II. Conversion to 7-Methyl-7H-pyrrolo[2,3-b]pyridine and Related Compounds J. Am. Chem. Soc. 1955, 77, 6554-6559
24. Yu, W. S.; Cheng, C. C.; Chang, C. P.; Wu, G. R.; Hsu, C. H.; Chou, P. T. Excited-State Double-Proton Transfer on 3-Methyl-7-azaindole in a Single Crystal: Deuterium Isotope/Tunneling Effect J. Phys. Chem. A 2002, 106, 8006-8012
25. Chou, P. T.; Yu, W. S.; Wei, C. Y.; Cheng, Y. M.; Yang, C. Y. Water-Catalyzed Excited-State Double Proton Transfer in 3-Cyano-7-azaindole: The Resolution of the Proton-Transfer Mechanism for 7-Azaindoles in Pure Water J. Am. Chem. Soc. 2001, 123, 3599-3600
26. Mente, S.; Maroncelli, M. Solvation and the Excited-State Tautomerization of 7-Azaindole and 1-Azacarbazole: Computer Simulations in Water and Alcohol Solvents J. Phys. Chem. A 1998, 102, 3860-3876
27. Kyrychenko, A.; Waluk, J. Excited-State Proton Transfer through Water Bridges and Structure of Hydrogen-Bonded Complexes in 1 H -Pyrrolo[3,2- h ] quinoline: Adiabatic Time-Dependent Density Functional Theory Study J. Phys. Chem. A 2006, 110, 11958-11967
28. Kyrychenko, A.; Stepanenko, Y.; Waluk, J. Molecular Dynamics and DFT Studies of Intermolecular Hydrogen Bonds between Bifunctional Heteroazaaromatic Molecules and Hydroxylic Solvents J. Phys. Chem. A 2000, 104, 9542-9555
29. Chen, Y.; Gai, F.; Petrich, J. W. Solvation of 7-Azaindole in Alcohols and Water: Evidence for Concerted, Excited-State, Double-Proton Transfer in Alcohols J. Am. Chem. Soc. 1993, 115, 10158-10166
30. Rich, R. L.; Chen, Y.; Neven, D.; Nbgrerie, M.; Gai, F.; Petrich, J. W. Steady-State and Time-Resolved Fluorescence Anisotropy of 7-Azaindole and Its Derivatives J. Phys. Chem. 1993, 97, 1781-1788
31. Bigeleisen, J. Statistical Mechanics of Isotopic Systems with Small Quantum Corrections. I. General Considerations and the Rule of the Geometric Mean J. Chem. Phys. 1955, 23, 2264-2267