The photochemistry of 8-bromo-2_-deoxyadenosine. A direct entry to cyclopurine lesions (Articolo in rivista)

Type

• Prodotto della ricerca (Classe)
• Articolo in rivista (Classe)

Label

• The photochemistry of 8-bromo-2_-deoxyadenosine. A direct entry to cyclopurine lesions (Articolo in rivista) (literal)

Anno

• 2004-01-01T00:00:00+01:00 (literal)

Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#doi

• 10.1039/b410939b (literal)

Alternative label

• Liliana B. Jimenez, Susana Encinas, Miguel A. Miranda, Maria Luisa Navacchia and Chryssostomos Chatgilialoglu (2004)
  The photochemistry of 8-bromo-2_-deoxyadenosine. A direct entry to cyclopurine lesions
  in Photochemical & photobiological sciences (Print)
  (literal)

Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#autori

• Liliana B. Jimenez, Susana Encinas, Miguel A. Miranda, Maria Luisa Navacchia and Chryssostomos Chatgilialoglu (literal)

Pagina inizio

• 1042 (literal)

Pagina fine

• 1046 (literal)

Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#numeroVolume

• 3 (literal)

Rivista

• Photochemical & photobiological sciences (Rivista)

Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#numeroFascicolo

• 11-12 (literal)

Note

• ISI Web of Science (WOS) (literal)

Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#affiliazioni

• Univ Politecn Valencia, CSIC, Inst Tecnol Quim, Dept Quim, E-46022 Valencia, Spain , ISOF, Consiglio Nazl Ric, I-40129 Bologna, Italy (literal)

Titolo

• The photochemistry of 8-bromo-2_-deoxyadenosine. A direct entry to cyclopurine lesions (literal)

Abstract

• The UV photolysis of 8-bromo-2'-deoxyadenosine has been investigated in different solvents and in the presence of additives like halide anions. Photolytic cleavage of the C-Br bond leads to formation of the C8 radical. In methanol, subsequent hydrogen abstraction from the solvent is the main radical reaction; however, in water or acetonitrile intramolecular hydrogen abstraction from the sugar moiety, to give the C5' radical, is the major path. This C5' radical undergoes a cyclization reaction on the adenine and gives the aminyl radical. A rate constant of 1.8 x 10(5) s(-1) has been measured by laser ash photolysis in CH3CN for this unimolecular process. Product studies from steady-state photolysis in acetonitrile have shown the conversion of 8-bromo-2'-deoxyadenosine to 5',8-cyclo-2'-deoxyadenosine in 65% yield and in a diastereoisomeric ratio (5'R) : (5'S) = 1.7. Evidence supporting that the equilibrium Brdegrees + Br-reversible arrow) Br-2(.-) plays an important role in this synthetically useful radical cascade is obtained by regulating the relative concentrations of the two reactive oxidizing species (literal)

Prodotto di

• MAteriali Funzionali Organici per applicazioni High-Tech: sistemi molecolari, supramolecolari e bioibridi (MAFO-HT) (PM.P04.003.003) (Modulo)
• Institute for organic syntheses and photoreactivity (ISOF) (Istituto)

Autore CNR

• MARIA LUISA NAVACCHIA (Persona)
• CHRYSSOSTOMOS CHATGILIALOGLU (Unità di personale interno)

Insieme di parole chiave

• Parole chiave di "The photochemistry of 8-bromo-2_-deoxyadenosine. A direct entry to cyclopurine lesions" (Insieme di parole chiave)

Incoming links:

Prodotto

• Institute for organic syntheses and photoreactivity (ISOF) (Istituto)
• MAteriali Funzionali Organici per applicazioni High-Tech: sistemi molecolari, supramolecolari e bioibridi (MAFO-HT) (PM.P04.003.003) (Modulo)

Autore CNR di

• CHRYSSOSTOMOS CHATGILIALOGLU (Unità di personale interno)
• MARIA LUISA NAVACCHIA (Persona)

Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#rivistaDi

• Photochemical & photobiological sciences (Rivista)

Insieme di parole chiave di

• Parole chiave di "The photochemistry of 8-bromo-2_-deoxyadenosine. A direct entry to cyclopurine lesions" (Insieme di parole chiave)