title: Photochemical behavior of 2-azidopurine tri-O-acetylribonucleoside in aqueous solution: unprecedented transformation into 1-(5'-O-acetyl-β-D-ribofuranosyl)-5-[(2-oxo-1,3,5-oxadiazocan-4-ylidene)amino]-1H-imidazole-4-carbaldehyde.
abstract: The photochemical behavior of 2-azidopurine 2',3',5'-tri-O-acetylribonucleoside has been investigated in aqueous solution under aerobic and anaerobic conditions. The two major processes under anaerobic irradiation of 2-azidopurine 2',3',5'-tri-O-acetylribonucleoside involve unprecedented transformation into 1-(5'-O-acetyl-β-D-ribofuranosyl)-5-[(2-oxo-1,3,5-oxadiazocan-4-ylidene)amino]-1H-imidazole-4-carbaldehyde and photoreduction to respective 2-aminopurine derivative, whereas under aerobic conditions these two processes occur to a much lesser extent and photooxidation to respective 2-nitropurine derivative dominates. The structures of photoproducts formed were confirmed by NMR and high-resolution electrospray ionization mass spectral data.
authors.affiliation: a Institute of Bioorganic Chemistry , Polish Academy of Sciences , Poznań , Poland.
authors.forename: Krzysztof
authors.initials: K
authors.lastname: Komodziński
authors.forename: Zofia
authors.initials: Z
authors.lastname: Gdaniec
authors.forename: Bohdan
authors.initials: B
authors.lastname: Skalski
mesh_terms: D002851:Chromatography, High Pressure Liquid; D013058:Mass Spectrometry; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D010777:Photochemistry; D012263:Ribonucleosides / Q000737:chemistry*; D012996:Solutions
chemical_list: D012263:Ribonucleosides; D012996:Solutions
keywords: 2-Azidopurine ribonucleoside; modified nucleoside; photochemistry; photooxidation; photoreduction