One-electron reduction of 8-bromoisoguanosine and 8-bromoxanthosine in the aqueous phase: Sequential versus concerted proton-coupled electron routes

Journal of Physical Chemistry Letters

Volumn 1, Issue 1, 2010, Pages 174-177

  Chatgilialoglu, Chryssostomos ^a   D'Angelantonio, Mila ^a   Kaloudis, Panagiotis ^a   Mulazzani, Quinto G ^a   Guerra, Maurizio ^a  

^a CNR   (Italy)

Author keywords

Biophysical chemistry

Indexed keywords

AQUEOUS PHASE; BIOPHYSICAL CHEMISTRY; DFT CALCULATION; ELECTRON-TRANSFER; HYDRATED ELECTRON; MONOANIONS; ONE-ELECTRON REDUCTIONS; PROTONATION STATE; PULSE RADIOLYSIS TECHNIQUE; PURINE DERIVATIVES;

HYDRATES; PROBABILITY DENSITY FUNCTION; PROTONS; RADIATION CHEMISTRY; RADIOLYSIS; SULFUR COMPOUNDS;

ELECTRONS;

EID: 77149143914     PISSN: None     EISSN: 19487185     Source Type: Journal    
DOI: 10.1021/jz9001532     Document Type: Article

References (16)

1. Chatgilialoglu, C.; Guerra, M.; Mulazzani, Q. G. Model Studiesof DNA C50 Radicals. Selective Generation and Reactivity of20-Deoxyadenosin-50-yl Radical. J. Am. Chem. Soc. 2003, 125,3839-3848.
2. Russo, M.; Jimenez, L. B.; Mulazzani, Q. G.; D'Angelantonio, M.; Guerra, M.; Miranda, M. A.; Chatgilialoglu, C. Chemical Radiation Studies of 8-Bromo-20-deoxyinosine and 8-Bromoi-nosine in Aqueous Solutions. Chem.;Eur. J. 2006, 12, 7684-7693.
3. Costentin, C.; Robert, M.; Saveant, J.-M. Fragmentation of Aryl Halide π Anion Radicals. Bending of the Cleaving Bondand Activation vs Driving Force Relationships. J. Am. Chem. Soc. 2004, 126, 16051-16057.
4. Chatgilialoglu, C.; Caminal, C.; Guerra, M.; Mulazzani, Q.G. Tautomers of One-Electron Oxidized Guanosine. Angew. Chem., Int. Ed. 2005, 44, 6030-6032.
5. Chatgilialoglu, C.; Caminal, C.; Altieri, A.; Vougioukalakis, G. C.; Mulazzani, Q. G.; Gimisis, T.; Guerra, M. Tautomerism inthe Guanyl Radical. J. Am. Chem. Soc. 2006, 128, 13796-13805.
6. Kaloudis, P.; D'Angelantonio, M.; Guerra, M.; Gimisis, T.; Mulazzani, Q. G.; Chatgilialoglu, C. One-Electron Reductionof 8-Bromo-2-aminoadenosine in the Aqueous Phase: Radia-tion Chemical and DFT Studies of the Mechanism. J. Phys. Chem. B 2008, 112, 5209-5217.
7. Candeias, L. P.; Steenken, S. Electron Adducts of Adenine Nucleosides and Nucleotides in Aqueous Solution: Proton-ation at Two Carbon Sites (C2 and C8) and Intra- and Intermolecular Catalysis by Phosphate. J. Phys. Chem. 1992,96,937-944.
8. D'Angelantonio, M.; Russo, M.; Kaloudis, P.; Mulazzani, Q. G.; Wardman, P.; Guerra, M.; Chatgilialoglu, C. Reaction of Hydrated Electrons with Guanine Derivatives: Tautomerismof Intermediate Species. J. Phys. Chem. B 2009, 113, 2170-2176.
9. Huynh, M. H. V.; Meyer, T. J. Proton-Coupled Electron Transfer. Chem. Rev. 2007, 107, 5004-5064 and references citedtherein.
10. Meyer, T. J.; Huynh, M. H. V.; Thorp, H. H. The Possible Role of Proton-Coupled Electron Transfer (PCET) in Water Oxidationby Photosystem II. Angew. Chem., Int. Ed. 2007, 46,5284-5304 and references cited therein.
11. Fecenko, C. J.; Thorp, H. H.; Meyer, T. J. The Role of Free Energy Change in Coupled Electron-Proton Transfer. J. Am. Chem. Soc. 2007, 129, 15098-15099.
12. Ross, A. B.; Mallard, W. G.; Helman, W. P.; Buxton, G. V.; Huie, R. E.; Neta, P. NDRL-NIST Solution Kinetic Database, ver. 3; Notre Dame Radiation Laboratory: Notre Dame, IN and NIST Standard Reference Data: Gaithersburg, MD, 1998, andreferences therein.
13. Frisch, M. J.; et al. Gaussian 03, Revision D.02; Gaussian, Inc.; WallingfordCT,2004.(SeeSupporting Informationforthefulllist of authors)
14. Kulikowska, E.; Kierdaszuk, B.; Shugar, D. Xanthine, Xantho-sine and Its Nucleosides: Solution Structures of Neutral and IonicForms, and Relevance toSubstratePropertiesin Various Enzyme Systems and Metabolic Pathways. Acta Biochim. Pol.2004,51,493-531.
15. Seela, F.; Wei, C.; Kazimierczuk, Z. Substituent Reactivity and Tautomerism of Isoguanosine and Related Nucleosides. Helv. Chim. Acta 1995, 78, 1843-1854.
16. Long, R. A.; Robins, R. K.; Townsend, L. B. Purine Nucleo-sides. XV. Synthesis of 8-Amino- and 8-Substituted Amino-purine Nucleosides. J. Org. Chem. 1967, 32, 2751-2756.