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The title compound. 9-(1,3-dihydroxy-2-propoxymethyl)adenine (DHP-Ade). an analogue of the antiviral acyclonucleoside 9-(1,3-dihydroxy-2-propoxymethyl)guanine (DHPG), crystallizes in the monoclinic space group P2 1 . with unit cell dimensions of a = 10.848(4), b = 8.765(3), c = 11.432(4) Å. β = 102.14(3)° . with two independent molecules in the asymmetric unit. The crystal structure of DHP-Ade was determined and compared with that for DHPG. The solution conformations of both acyclonucleosides were also determined with the aid of  1 H and , 13 C NMR spectroscopy. In the solid state the acyclic chain may adopt a “folded” form, i.e. gauche about the C(1′)-O(1′) bond (as in DHP-Ade), or an “extended” form (as in DHPG), results which corre- spond to the rotations about this bond in solution. A general discussion is presented of the conformations of the acyclic chains of various acyclonucleosides, from the antiviral 9-(2-hydroxyethoxymethyl)guanine (Acyclovir, ACV) through to 2′,3′-seco-nucleosides, both in the solid state and in solution, and the relevance of these to biological activities.

Solid State and Solution Structures of an Adenine Analogue of the Antiviral Acyclonucleoside 9-(1,3-Dihydroxy-2-propoxymethyl)guanine