title: Phosphorylation of AMP by inorganic phosphorylating agents.
abstract: AMP was phosphorylated by inorganic phosphorylating agents: cyclo-triphosphate and diphosphonate, in aqueous solution (70-80 degrees C, pH 6-12). The molecular structures of phosphorylated products were established by use of phosphorus-31 NMR and high-performance liquid chromatography (HPLC). The OH groups on AMP were phosphorylated by both phosphorylating agents to form 2'- or 3'-phosphate but an OH group on dAMP was not phosphorylated. Phosphorylation of OH group proceeds in two steps: formation of hydrogen bond between OH group and phosphorylating agent; subsequent nucleophilic attack of OH group on a phosphorus atom. Phosphate group on AMP was phosphorylated by diphosphonate but not by cyclo-triphosphate. The difference in the reactivities is explained in terms of charge repulsion between AMP and agents.
mesh_terms: D000249:Adenosine Monophosphate / Q000031:analogs & derivatives*; D002851:Chromatography, High Pressure Liquid; D004164:Diphosphonates; D009682:Magnetic Resonance Spectroscopy; D010710:Phosphates; D010766:Phosphorylation
chemical_list: D004164:Diphosphonates; D010710:Phosphates; D000249:Adenosine Monophosphate