Unraveling the photochemistry of the 5-azido-2'-deoxyuridine photoaffinity label.
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.
Gourdain
Stéphanie
S
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.
Martinez
Agathe
A
Petermann
Christian
C
Harakat
Dominique
D
Clivio
Pascale
P
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
D001386:Azides; D003432:Cross-Linking Reagents; D003856:Deoxyuracil Nucleotides; D014867:Water; C048865:5-azido-2'-deoxyuridine 5'-triphosphate; D002244:Carbon; D004247:DNA; D003857:Deoxyuridine