Adenosine Monophosphate → Adenosine

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Dinucleotide 24 afforded phosphonate 20 and adenosine 5′-monophosphate 21 in about 60% yield. 9-(β-D-Furanosyl)adenine-3′-[[1-(adenin-7-yl-ethoxy)methyl]-phosphonate] gave adenosine (40% yield) and 20 (60% yield). Dinucleotide analog 25, having a butenolide ester unit, was found to be stable to the enzyme.Compound 24, possessing both the skeletons of phosphonate 20 and 5′-adenosine monophosphate 21, was dephosphorylated at the 5′-position by snake venom in 80% yield after 8 h. The resultant 9-(b-D-furanosyl)adenine-3′-[[1-(adenin-7-yl-ethoxy)methyl]phosphonate] was hydrolyzed further in the presence of spleen phosphodiesterase to afford adenosine and phosphonate 20 in about 40-60% yield after 8 h. See, Hakimelahi et al. (1995) J. Med. Chem. 38: 4648-4659 and references cited therein. Spleen phosphodiesterase also degraded compound 24 to give 5′-adenosine monophosphate 21 and phosphonate 20 in an overall yield of 60% after 8 h. These results indicate that the phosphodiesterases recognized dinucleotide analog 24 as a normal substrate. In addition, it was found that nucleotide-containing butenolide 25 was completely resistant to snake venom and spleen enzymes.

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