38709-53-4Relevant academic research and scientific papers
Reactions des radicaux 6-hydroxy-5,6-dihydrothymid-5-yles en solution aqueuse
Berger, M.,Sarrazin, F.,Cadet, J.
, p. 853 - 862 (2007/10/02)
The main reactions of 6-hydroxy-5,6-dihydrothymid-5-yl radicals, specifically obtained by electron capture dissociation of the trans diastereomers of 5-bromo-6-hydroxy-5,6-dihydrothymidine, were determined in aqueous solutions on the basis of final product analysis.In oxygen-free aqueous solutions a complex mixture of both monomeric and dimeric decomposition products was produced.It is worth mentioning the radiation-induced formation of modified nucleosides which involves the transient generation of 5-(2'-deoxyuridyl)methyl radical.This may be explained in terms of initial formation of 6-hydroxy-5,6-dihydrothymid-5-yl radicals, followed by dehydration and subsequent deprotonation.
Oxidation of Thymidine by Peroxymono- and Peroxodisulfate Ions
Itahara, Toshio,Koga, Sunao
, p. 85 - 88 (2007/10/02)
Oxidation of thymidine by KHSO5 gave thymidine glycols, while a similar treatment with Na2S2O8 gave 5-hydroxymethyl-2'-deoxyuridine.
Identification of the Products resulting from the Direct effects of γ-Radiation on Thymidine
Shaw, Anthony A.,Voituriez, Lucienne,Cadet, Jean,Gregoli, Silvano,Symons, Martyn C.
, p. 1303 - 1308 (2007/10/02)
The products formed upon γ-irradiation of thymidine in frozen aqueous solution have been identified.These products may all be explained in terms of the fates of now well documented primary charged radical species, and our results complement well those of previous e.s.r. studies on those primary and secondary radicals.In order to probe the mechanisms of formation of the major products, we have carried out experiments using heavy isotopes, including deuterium oxide and (18)O2.The radical cation undergoes both hydration, yielding the four isomers of 6-hydroxy-5,6-dihydrothymidine, and deprotonation at the methyl group to yield 5-hydroxymethyl-2'-deoxyuridine.As expected, the radical anion reacts primarily by protonation at C-6 to yield the (5R)- and (5S)-diastereoisomers of 5,6-dihydrothymidine and 5-hydroxy-5,6-dihydrothymidine.Excitation processes were shown to occur by the observation of the thymidine cyclobutane dimers.The release of significant amounts of thymine and 2-deoxy-D-ribono-1,4-lactone indicates the formation of radicals centred within the sugar moiety.The proposed role of the initial charged radicals in the formation of certain products has been supported by quantitative experiments carried out using compounds expected to be electron scavengers and electron donors with respect to thymidine.Finally, subsequent to our earlier paper on the e.s.r. identification of the radicals formed upon irradiation of thymidine bromohydrin in frozen aqueous solution, we have isolated the products formed on annealing and identified them as thymidine and 5-hydroxymethyl-2'-deoxyuridine.We discuss their mechanisms of formation.
Radiation-Induced Degradation of Purine and Pyrimidine 2'-Deoxyribonucleosides in Aqueous KBr Solutions
Cadet, J.,Voituriez, L.,Berger, M.,Myers, L. S., (Jr.)
, p. 1643 - 1651 (2007/10/02)
Steady-state γ-radiolysis of 5E-4 M pyrimidine and purine 2'-deoxyribonucleosides in aqueous solutions saturated with N2, N2O and O2, respectively, have been carried out in the presence of 0.1 M KBr.The main final degradation products have been isolated and characterised by various spectroscopic measurements including 1H and 13C NMR, UV, C.D. and mass spectrometry.The radiation-induced decomposition of thymidine is mostly accounted for by an ionic mechanism involving Br2, the decay product of Br2, as the reactive oxidising specie.On the other hand the degradation of the purine ring of 2'-deoxyadenosine and 2'-deoxyguanosine may be accounted for by the action of Br2 or Br3. - Keywords: 2'-Deoxyribonucleosides, Inorganic Radical, γ-Irradiation, Radical Reactions, Thymidine Oxidation
