Crystal structure of a nucleoside model for the inter-strand cross-link formed by the reaction of 2'-de-oxy-guanosine and an abasic site in duplex DNA

Michael J Catalano; Kasi Viswanatharaju Ruddraraju; Charles L Barnes; Kent S Gates

doi:10.1107/S205698901600517X

Crystal structure of a nucleoside model for the inter-strand cross-link formed by the reaction of 2'-de-oxy-guanosine and an abasic site in duplex DNA

Acta Crystallogr E Crystallogr Commun. 2016 Apr 5;72(Pt 5):624-7. doi: 10.1107/S205698901600517X. eCollection 2016 May 1.

Authors

Michael J Catalano¹, Kasi Viswanatharaju Ruddraraju¹, Charles L Barnes¹, Kent S Gates¹

Affiliation

¹ 125 Chemistry Bldg, University of Missouri-Columbia, MO 65211, USA.

Abstract

The title compound, 9-[(2R,4S,5R)-4-hy-droxy-5-(hy-droxy-meth-yl)tetra-hydro-furan-2-yl]-2-{[(2R,4S,5R)-4-meth-oxy-5-(meth-oxy-meth-yl)tetra-hydro-furan-2-yl]amino}-1H-purin-6(9H)-one, C17H25N5O7, crystallizes with two independent mol-ecules (A and B) in the asymmetric unit. In the crystal, the guanosine moieties of mol-ecules A and B are linked by N-H⋯N and O-H⋯N hydrogen-bonding inter-actions, 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 inter-actions to complete the three-dimensional structure.

Keywords: 2′-deoxyguanosine; crystal structure; deoxy-d-ribofuranose; glycosidic linkage; hydrogen bonding; nucleobase; purine-6(9H)-one.