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The title compound crystallizes in space group P 4 s 2 1 2 with a-b=9.558 Å, c = 36.649 Å. The structure has been determined by direct methods on the basis of 1624 X-ray counter data and refined by least squares methods to R = 6.7%. The acidic proton resides at the carboxyl group and not at adenine N(1) and the acetal methyl group is exo while the bulkier carboxyethyl group is endo relative to the ribose. The nucleoside occurs in the syn conformation, the conformation about C(4′)-C(5′) is trans, gauche, thus prohibiting an intramolecular O (5′) - H ... N (3) hydrogen bond. The ribose is in a slightly puckered C(3′)-exo envelope conformation, the carboxyethyl group is all-lrans rendering the molecule in an extended form with a distance 11 Å between the carboxyl group and amino group N(6). The acetal methyl group in exo displays a pmr signal at 1.35 ppm and can serve to distinguish the two methyl signals of O-2′,3′-isopropylideneadenosine at 1.38 ppm and at 1.65 ppm.

X-Ray Structure of 2′,3′-O-(2-Carboxyethyl)-ethylideneadenosine A Spacer Extended Ligand for Affinity Resins