THE SYNTHESIS AND PROPERTIES OF ADENOSINE-2′ DIPHOSPHATE AND ADENOSINE-3′ DIPHOSPHATE

Abstract

Adenosine-2′ diphosphate (A2'DP) and adenosine-3′ diphosphate (A3′DP) have been prepared by reaction between the corresponding mononucleotides with phosphoramidic acid in formamide. The products were isolated by ion-exchange chromatography on DEAE-cellulose and characterized by enzymic and chemical methods. A major side reaction in the synthesis is the phosphorylation of unprotected hydroxyl groups oil the nucleotides. A2′DP and A3′DP were found to be more labile than adenosine-5′ diphosphate, and to decompose at neutral pH by direct hydrolysis of the pyrophosphate bond as well as by formation of adenosine-2′,3′ cyclic phosphate. They are stable in 10% trichloroacetic acid at 0° for 10 minutes. Phosphomonoesterase degrades both to nucleosides by way of the corresponding nucleoside monophosphates. Ribonuclease T2does not attack A2′DP but degrades A3′DP to adenosine-3′ phosphate. Neither nucleotide is degraded by snake venom or spleen phosphodiesterases under conditions where oligonucleotides are completely hydrolyzed.