title: Unraveling the photochemistry of the 5-azido-2'-deoxyuridine photoaffinity label.
abstract: UV irradiation of 5-azido-2'-deoxyuridine in water provides up to seven products. All likely result from a pivotal azirene, formed by the intramolecular rearrangement of the initially formed nitrene, that undergoes nucleophilic addition at its C5 position. This study strongly suggests that only nucleophilic amino acid residues in close proximity are cross-linkable in photolabeling experiments by using the 5-azidouracil photophore.
authors: Université de Reims Champagne Ardenne, Institut de Chimie Moléculaire de Reims, CNRS UMR 6229, UFR de Pharmacie, 51 rue Cognacq-Jay, 51096 Reims Cedex, France.
authors: Stéphanie
authors: S
authors: Gourdain
authors: Agathe
authors: A
authors: Martinez
authors: Christian
authors: C
authors: Petermann
authors: Dominique
authors: D
authors: Harakat
authors: Pascale
authors: P
authors: Clivio
mesh_terms: D001386:Azides / Q000138:chemical synthesis* / Q000737:chemistry; D001665:Binding Sites; D002244:Carbon / Q000737:chemistry; D002625:Chemistry, Organic / Q000379:methods*; D003432:Cross-Linking Reagents / Q000737:chemistry; D004247:DNA / Q000737:chemistry; D003856:Deoxyuracil Nucleotides / Q000138:chemical synthesis* / Q000737:chemistry; D003857:Deoxyuridine / Q000138:chemical synthesis* / Q000737:chemistry*; D015195:Drug Design; D006863:Hydrogen-Ion Concentration; D008027:Light; D008956:Models, Chemical; D015394:Molecular Structure; D010777:Photochemistry / Q000379:methods*; D014466:Ultraviolet Rays; D014867:Water / Q000737:chemistry
chemical_list: D001386:Azides; D003432:Cross-Linking Reagents; D003856:Deoxyuracil Nucleotides; D014867:Water; C048865:5-azido-2'-deoxyuridine 5'-triphosphate; D002244:Carbon; D004247:DNA; D003857:Deoxyuridine