2-Amino-8-(2-deoxy-2-fluoro-beta-D-arabinofuranosyl)imidazo[1,2-a][1 ,3,5]-triazin-4(8H)-one monohydrate, a 2 `-deoxyguanosine analogue with an altered Watson-Crick recognition site

Autor(en): Jiang, Dawei
Budow, Simone
Glacon, Virginie
Eickmeier, Henning
Reuter, Hans 
He, Yang
Seela, Frank
Stichwörter: Chemistry; Chemistry, Multidisciplinary; CONFORMATION; Crystallography; NUCLEOSIDE
Erscheinungsdatum: 2010
Herausgeber: INT UNION CRYSTALLOGRAPHY
Journal: ACTA CRYSTALLOGRAPHICA SECTION C-STRUCTURAL CHEMISTRY
Volumen: 66
Ausgabe: 4
Startseite: O194-O197
Zusammenfassung: 
The title compound, C10H12FN5O4 center dot H2O, shows an anti glycosyl orientation [chi = -123.1 (2)degrees] The 2-deoxy-2-fluoroarabino-furanosyl moiety exhibits a major C2'-endo sugar puckering (S-type, C2'-endo-C1'-exo, T-2(1)), with P = 156.9 (2)degrees and pi(m) = 36.8 (1)degrees, while in solution a predominantly N conformation of the sugar moiety is observed. The conformation around the exocyclic C4'-C5' bond is -sc (trans, gauche), with gamma = -78.3 (2)degrees. Both nucleoside and solvent molecules participate in the formation of a three-dimensional hydrogen-bonding pattern via intermolecular N-H center dot center dot center dot O and O-H center dot center dot center dot O hydrogen bonds; the N atoms of the heterocyclic moiety and the F substituent do not take part in hydrogen bonding.
ISSN: 20532296
DOI: 10.1107/S0108270110008036

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