Synthesis of a photoaffinity-spin-labeled derivative of ATP and its first application to F1-ATPase.
The synthesis of an ATP derivative is described, in which a spin-label is attached to the 3'-position of the ribose moiety and an azido group to C8 of the adenine ring (SL-N3-ATP). Irradiation of this compound at 350 nm generates a nitrene, which will react with any functional group in its vicinity. SL-N3-ATP exhibits a strongly immobilized ESR spectrum in a complex with F1-ATPase from beef heart mitochondria. It was covalently incorporated into this enzyme. SL-N3-ATP may be employed in ESR investigations under conditions in which non-covalent interactions are too weak for motionally restricted species to be easily observed.
D000255:Adenosine Triphosphate / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000378:metabolism; D000818:Animals; D001386:Azides / Q000138:chemical synthesis* / Q000378:metabolism; D002417:Cattle; D004578:Electron Spin Resonance Spectroscopy; D007700:Kinetics; D008929:Mitochondria, Heart / Q000378:metabolism*; D006180:Proton-Translocating ATPases / Q000378:metabolism*; D013113:Spin Labels / Q000138:chemical synthesis*
D001386:Azides; D013113:Spin Labels; C054794:3'(O)-(1-oxyl-2,2,5,5-tetramethyl-3-carbonyl pyrrolidine)-8-azidoadenosine 5'-triphosphate; C026652:3'-O-(1-oxyl-2,2,5,5-tetramethyl-3-carbonyl pyrrolidine)-adenosine 5'-triphosphate; D000255:Adenosine Triphosphate; D006180:Proton-Translocating ATPases