Cyclization of the phosphorus chain of the methylene-bridged analogs of adenosine triphosphate

The phosphorus-containing side chains of two methylene-bridged analogs of adenosine triphosphate have been cyclized to produce the corresponding analogs of monoadenosine-5′-trimetaphosphate: adenosine-5′-O P(O)OP(O)(OH)CH 2P(O)(OH)O and adenosine-5′-O P*(O)CH 2P(O)(OH)OP(O)(OH)O The molecules, which were generated in anhydrous media through a carbodi- imide-mediated condensation, were characterized by 31P nuclear-magnetic resonance, and the white-noise 1H decoupled spectra were simulated. These molecules are quite reactive and readily converted to their corresponding linear forms upon hydrolysis. The second structure contains an asymmetric phosphorus atom, and both of the possible cyclic molecules have been ob- served and the diasteroisometric mixture has been isolated.