Dehydration promotes phosphoramidate-linked amino acidyl and peptido adenosine conjugates

Abstract

Cyclic nucleoside phosphates have been shown previously to be adequately activated to oligomerise under dry conditions. Herein, it is demonstrated that 3′,5′-cyclic adenosine monophosphate (3′,5′-cAMP) and glycine when subjected to dehydration under alkaline conditions form phosphoramidate-linked conjugates. Solid-state reaction mechanisms investigated by DFT suggest why the reaction does not occur efficiently in the aqueous phase.