Theoretical study of the ring-closing reaction of 5 '-AMP to cAMP and H2O in the gas phase

摘要

The ring-closing reaction of 5'-adenosine monophosphate (5'-AMP) to generate cyclic 3', 5'-adenosine monophosphate (cAMP) and H2O was theoretically investigated at the B3LYP/6-31G**level. It was found that the ring-closing reaction of 5'-AMP may proceed in a synchronous way or in a stepwise way. For the latter, the reaction is a multichannel elimination reaction including inner H transfer. The potential energy surface of Path 3 is lowest in all the ring-closing reaction paths. In addition, H shuttling reaction with the participation of a water molecule to act as a shuttle were also studied at the same level. The calculations indicate that the participation of a water molecule facilitates hydrogen transfer reaction. Our present calculations rationalized all the possible reaction channels. (c) 2005 Wiley Periodicals, Inc.