Hydrolysis of 2'- and 3'-C-Methyluridine 2',3'-Cyclic Monophosphates and Interconversion and Dephosphorylation of the Resulting 2'- and 3'-Monophosphates: Comparision with the Reactions of Uridine Monophosphates

Article abstract of DOI:10.1021/jo00041a014

2',3'-Cyclic monophosphates of 2'- and 3'-C-methyluridines have been prepared and shown to hydrolyze to a mixture of the corresponding 2'- and 3'-monophosphates.The predominant product isomer is the one having the tertiary hydroxyl group phosphorylated, but on longer treatment a phosphate migration from the tertiary to secondary hydroxyl function takes place.Hydrolytic dephosphorylation competes with the phosphate migration, the tertiary hydroxyl group being dephosphorylated 1 order of magnitude faster than the secondary one.Kinetics of the partial reactions have been described and compared to the data obtained with uridine 2',3'-cyclic monophosphate.The tertiary monophosphate has been shown to be exceptionally susceptible to nucleophilic attack of the neighboring hydroxyl group.