7-Fluorotubercidin: a halogenated derivative of a naturally occurring nucleoside antimetabolite

Autor(en): Seela, Frank
Ming, Xin
Budow, Simone
Eickmeier, Henning
Reuter, Hans 
Stichwörter: 2'-DEOXYTUBERCIDIN; ANALOGS; Chemistry; Chemistry, Multidisciplinary; CRYSTAL; Crystallography; NUCLEIC-ACIDS; REPLICATION; RINGS; TUBERCIDIN
Erscheinungsdatum: 2008
Herausgeber: WILEY-BLACKWELL
Journal: ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS
Volumen: 64
Ausgabe: 5
Startseite: O293-O295
Zusammenfassung: 
The title compound [systematic name: 4-amino-5-uoro-7-(beta-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine], C(11)H(13)FN(4)O(4), exhibits an anti glycosylic bond conformation, with a chi torsion angle of -124.7 (3)degrees. The furanose moiety shows a twisted C2'-endo sugar pucker (S-type), with P = 169.8 (3)degrees and tau m = 38.7 (2)degrees. The orientation of the exocyclic C4'-C5' bond is sc (gauche, gauche), with a gamma torsion angle of 59.3 (3)degrees. The nucleobases are stacked head-to-head. The extended crystal structure is a three-dimensional hydrogen-bond network involving O-H center dot center dot center dot O, O-H center dot center dot center dot N and N-H center dot center dot center dot O hydrogen bonds. The crystal structure of the title nucleoside demonstrates that the C-C bonds nearest the F atom of the pyrrole system are significantly shortened by the electronegative halogen atom.
ISSN: 01082701
DOI: 10.1107/S0108270108010160

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