The 7-bromo derivative of 2-amino-2 `-deoxytubercidin fluorinated at the sugar moiety

Autor(en): Seela, Frank
Ding, Ping
Peng, Xiaohua
Eickmeier, Henning
Reuter, Hans 
Stichwörter: 2'-DEOXY-2'-FLUORO-BETA-D-ARABINONUCLEOSIDES; ANALOGS; Chemistry; Chemistry, Multidisciplinary; CONFORMATION; Crystallography; DNA; DUPLEX STABILITY; NUCLEOSIDE; OLIGONUCLEOTIDES
Erscheinungsdatum: 2007
Herausgeber: BLACKWELL PUBLISHING
Journal: ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS
Volumen: 63
Ausgabe: 10
Startseite: O600-O602
Zusammenfassung: 
The title compound, 2,4-diamino-5-bromo-7-(2-deoxy-2-uorofi-d-arabinofuranosyl)-7H-pyrrolo[ 2,3-d] pyrimidine, C11H13BrFN5O3, shows two conformations of the exocyclic C4' C5' bond, with the torsion angle gamma (O5' -C5'0 -C4' -C3') being 170.1 (3) degrees for conformer 1 (occupancy 0.69) and 60.7 (7) degrees for conformer 2 (occupancy 0.31). The N-glycosylic bond exhibits an anti conformation, with x =. 114.8 (4) degrees. The sugar pucker is N-type (C3'-endo; (3) T-4), with P = 23.3 (4)degrees and tau(m) m = 36.5 (2) degrees. The compound forms a three-dimensional network that is stabilized by several intermolecular hydrogen bonds (N -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 Br).
ISSN: 01082701
DOI: 10.1107/S0108270107027138

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