Abstract
Abstract Ap(NH2)dT was synthesized as a model compound for a study of the stability of the phosphodiester-amide interribonucleotide linkage in neutral aqueous solution, by photolyzing AnBnp(NH2)dT in anhydrous p-dioxane. Ap(NH2)dT proved to be unstable even under anhydrous conditions and could not be isolated. It was rapidly decomposed in neutral aqueous buffer solution, at 25°C, to give A>p, dT and ApdT. Three unstable intermediates of this decomposition, A>pNH2, ApNH2 and A>pdT were detected by 31P NMR. On the basis of the structure of the products, a mechanism is proposed for the decomposition.
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