2 `-Deoxy-5-propynyluridine: a nucleoside with two conformations in the asymmetric unit
Autor(en): | Budow, Simone Eickmeier, Henning Reuter, Hans Seela, Frank |
Stichwörter: | Chemistry; Chemistry, Multidisciplinary; CRYSTAL; Crystallography; DNA; MOLECULAR-STRUCTURE; OLIGODEOXYNUCLEOTIDES; PYRIMIDINES; RNA; STABILITY | Erscheinungsdatum: | 2009 | Herausgeber: | WILEY-BLACKWELL | Journal: | ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS | Volumen: | 65 | Ausgabe: | 12 | Startseite: | O645-O648 | Zusammenfassung: | The title compound, 1-(2-deoxy-beta-D-erythro-pentofuranosyl)-5-(prop-1-ynyl)pyrimidin-2,4(1 H,3H)-dione, C(12)H(14)N(2)O(5), shows two conformations in the crystalline state: conformer 1 adopts a C2'-endo (close to (2)E; S-type) sugar pucker and an anti nucleobase orientation [chi = -134.04 (19)degrees], while conformer 2 shows an S sugar pucker (twisted C2'-endo-C3'-exo), which is accompanied by a different anti base orientation [chi = -162.79 (17)degrees]. Both molecules show a sc (gauche, gauche) conformation at the exocyclic C4'-C5' bond and a coplanar orientation of the propynyl group with respect to the pyrimidine ring. The extended structure is a three-dimensional hydrogen- bond network involving intermolecular N-H center dot center dot center dot O and O-H center dot center dot center dot O hydrogen bonds. Only O atoms function as H-atom acceptor sites. |
ISSN: | 01082701 | DOI: | 10.1107/S0108270109044850 |
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geprüft am 03.05.2024