2-Amino-8-(2-deoxy-2-fluoro-β-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

The title compound, C10H12FN5O4·H2O, shows an anti glycosyl orientation [χ = −123.1 (2)°]. The 2‐deoxy‐2‐fluoroarabinofuranosyl moiety exhibits a major C2′‐endo sugar puckering (S‐type, C2′‐endo–C1′‐exo, 2T1), with P = 156.9 (2)° and τm = 36.8 (1)°, while in solution a predominantly N conformation o...

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Bibliographic Details
Published in:Acta crystallographica. Section C, Crystal structure communications Crystal structure communications, 2010-04, Vol.66 (4), p.o194-o197
Main Authors: Jiang, Dawei, Budow, Simone, Glaçon, Virginie, Eickmeier, Henning, Reuter, Hans, He, Yang, Seela, Frank
Format: Article
Language:English
Subjects:
Crystallography
Crystallography, X-Ray
Deoxyguanosine - analogs & derivatives
Deoxyguanosine - chemistry
Heterocyclic Compounds - chemistry
Hydrogen Bonding
Hydrogen bonds
Molecular Conformation
Molecular Structure
Solutions - chemistry
Solvents - chemistry
Stereoisomerism
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Summary:The title compound, C10H12FN5O4·H2O, shows an anti glycosyl orientation [χ = −123.1 (2)°]. The 2‐deoxy‐2‐fluoroarabinofuranosyl moiety exhibits a major C2′‐endo sugar puckering (S‐type, C2′‐endo–C1′‐exo, 2T1), with P = 156.9 (2)° and τm = 36.8 (1)°, 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 γ = −78.3 (2)°. Both nucleoside and solvent molecules participate in the formation of a three‐dimensional hydrogen‐bonding pattern via intermolecular N—H...O and O—H...O hydrogen bonds; the N atoms of the heterocyclic moiety and the F substituent do not take part in hydrogen bonding.
ISSN:0108-2701
1600-5759
DOI:10.1107/S0108270110008036