Purine → Adenine

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Purine-containing oligonucleoside methylphosphonates may be depurinated by treatment by hydrochloric acid at 65° C. The methylphosphonate linkage is resistant to hydrolysis by these conditions as shown by the stability of d-TpT and d-TpTpT. On the other hand, dimers or trimers containing purine bases such as d-ApA, dApT, dTpA or d-ApApA have half-lives between 92 and 144 min in 0.01 M hydrochloric acid. Following neutralization with ammonium hydroxide, the products of these reactions were characterized by reversed phase HPLC. d-ApA gave adenine, while both d-ApT and d-TpA gave adenine and thymidine as the sole products of the reaction. Adenine and d-ApA were the only products observed when d-ApApA was partially hydrolyzed. When d-CpCpApT was completely hydrolyzed in acid three products, d-CpC, adenine and thymidine, were observed in a molar ratio of 1:1:1.

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