Crystal structure of a nucleoside model for the interstrand cross-link formed by the reaction of 2′-deoxyguanosine and an abasic site in duplex DNA

• Main Authors: Michael J. Catalano, Kasi Viswanatharaju Ruddraraju, Charles L. Barnes, Kent S. Gates
• Format: Article
• Language: English
• Published: International Union of Crystallography 2016-05-01
• Series: Acta Crystallographica Section E: Crystallographic Communications
• Subjects: crystal structure; purine-6(9H)-one; 2′-deoxyguanosine; deoxy-D-ribofuranose; glycosidic linkage; nucleobase; hydrogen bonding
• Online Access: http://scripts.iucr.org/cgi-bin/paper?S205698901600517X

The title compound, 9-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-2-{[(2R,4S,5R)-4-methoxy-5-(methoxymethyl)tetrahydrofuran-2-yl]amino}-1H-purin-6(9H)-one, C17H25N5O7, crystallizes with two independent molecules (A and B) in the asymmetric unit. In the crystal, the guanosine moieties of molecules A and B are linked by N—H...N and O—H...N hydrogen-bonding interactions, forming ribbons which are stacked to form columns along [100]. These columns are then linked by O—H...O hydrogen bonds between the ribose moieties and numerous C—H...O interactions to complete the three-dimensional structure.