143995-02-2Relevant articles and documents
N6-Substituent Effect on the Photooxidation of 2',3'-O-Isopropylideneadenosines with a Pyrimidopteridinetetraone N-Oxide. Chemical Evidence for the Generation and Reactivity of Adenosyl Cation Radicals
Sako, Magoichi,Makino, Toru,Kitada, Yukio,Hirota, Kosaku,Maki, Yoshifumi
, p. 1801 - 1806 (2007/10/02)
A comparative study on the photooxidation of 2',3'-O-isopropylideneadenosine 1a and its N6-benzoyl, N-6-monomethyl, and N6,N6-dimethyl derivatives, 1b-d, with a pyrimidopteridinetetraone N-oxide (PPO) was carried out.The ease of photooxidative consumption of the adenosines by the PPO is in the order 1d > 1c > 1a > 1b, which is parallel to their oxidation-peak potentials.Although substrates 1a and 1b underwent oxidative intramolecular cyclisation to the corresponding 5'-O,8-cycloadenosines, 2a and 2b, even in low yield, substrates 1c and 1d were exclusively oxidised at the N6-methyl group to give the corresponding N6-formyl derivatives, 3 and 4, together with minor amounts of demethylated products, 1a and 1c.The present observations provide chemical evidence for the generation and reactivity of adenosyl cation radicals.