We have synthesized adenosine and 7-methylguanosine 5‘-diphosphate imidazolides from imidazole
and the corresponding nucleoside 5‘-diphosphates. The phosphorimidazolide bond of the compounds
was susceptible to hydrolysis and hydrolyzed gradually in neutral aqueous solution, but it was
more stable than that of the corresponding imidazolides of nucleoside 5‘-monophosphate. The
7-methylguanosine 5‘-diphosphate imidazolide reacted with guanosine 5‘-monophosphate or 5‘-monophosphorylated oligoribonucleotides in neutral aqueous solution in the presence of an Mn2+
ion catalyst converting to the cap portion of mRNA or the capped m7Gppp-oligoribonucleotides in
substantial yields. The condensation reaction of adenosine 5‘-diphosphate imidazolide with adenosine
5‘-monophosphate took place similarly in neutral aqueous solution by a divalent metal ion-catalyst
such as Mg2+ or Mn2+, yielding diadenosine 5‘,5‘-triphosphate.
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