title: 7-Cyclopropyl-2'-deoxytubercidin: a carbocyclic side-chain derivative of 7-deaza-2'-deoxyadenosine.
abstract: The title compound {systematic name: 4-amino-5-cyclopropyl-7-(2-deoxy-β-D-erythro-pentofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine}, C14H18N4O3, exhibits an anti glycosylic bond conformation, with the torsion angle χ = -108.7 (2)°. The furanose group shows a twisted C1'-exo sugar pucker (S-type), with P = 120.0 (2)° and τm = 40.4 (1)°. The orientation of the exocyclic C4'-C5' bond is -ap (trans), with the torsion angle γ = -167.1 (2)°. The cyclopropyl substituent points away from the nucleobase (anti orientation). Within the three-dimensional extended crystal structure, the individual molecules are stacked and arranged into layers, which are highly ordered and stabilized by hydrogen bonding. The O atom of the exocyclic 5'-hydroxy group of the sugar residue acts as an acceptor, forming a bifurcated hydrogen bond to the amino groups of two different neighbouring molecules. By this means, four neighbouring molecules form a rhomboidal arrangement of two bifurcated hydrogen bonds involving two amino groups and two O5' atoms of the sugar residues.
authors.affiliation: Laboratorium für Organische und Bioorganische Chemie, Institut für Chemie neuer Materialien, Universität Osnabrück, Barbarastrasse 7, 49069 Osnabrück, Germany.
authors.forename: Haozhe
authors.initials: H
authors.lastname: Yang
authors.affiliation: Laboratory of Bioorganic Chemistry and Chemical Biology, Center for Nanotechnology, Heisenbergstrasse 11, 48149 Münster, Germany.
authors.forename: Simone
authors.initials: S
authors.lastname: Budow-Busse
authors.affiliation: Anorganische Chemie II, Institut für Chemie neuer Materialien, Universität Osnabrück, Barbarastrasse 7, 49069 Osnabrück, Germany.
authors.forename: Henning
authors.initials: H
authors.lastname: Eickmeier
authors.affiliation: Anorganische Chemie II, Institut für Chemie neuer Materialien, Universität Osnabrück, Barbarastrasse 7, 49069 Osnabrück, Germany.
authors.forename: Hans
authors.initials: H
authors.lastname: Reuter
authors.affiliation: Laboratorium für Organische und Bioorganische Chemie, Institut für Chemie neuer Materialien, Universität Osnabrück, Barbarastrasse 7, 49069 Osnabrück, Germany.
authors.forename: Frank
authors.initials: F
authors.lastname: Seela
mesh_terms: D002241:Carbohydrates / Q000737:chemistry*; D018360:Crystallography, X-Ray; D006031:Glycosylation; D006860:Hydrogen Bonding; D008968:Molecular Conformation; D009005:Monosaccharides / Q000737:chemistry*; D014372:Tubercidin / Q000031:analogs & derivatives* / Q000737:chemistry
chemical_list: C000595901:4-amino-5-cyclopropyl-7-(2-deoxy-beta-D-erythro-pentofuranosyl)-7H-pyrrolo(2,3-d)pyrimidine); D002241:Carbohydrates; D009005:Monosaccharides; C053222:2'-deoxytubercidin; D014372:Tubercidin
keywords: 7-cyclopropyl-2′-deoxytubercidin; 7-deazapurine; crystal structure; cyclopropane; hydrogen bonding; nucleoside