title: 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.
abstract: The title compound, C(10)H(12)FN(5)O(4).H(2)O, shows an anti glycosyl orientation [chi = -123.1 (2) degrees]. The 2-deoxy-2-fluoroarabinofuranosyl moiety exhibits a major C2'-endo sugar puckering (S-type, C2'-endo-C1'-exo, (2)T(1)), with P = 156.9 (2) degrees and tau(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...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.
authors.affiliation: Laboratory of Bioorganic Chemistry and Chemical Biology, Center for Nanotechnology, Heisenbergstrasse 11, 48149 Münster, Germany.
authors.forename: Dawei
authors.initials: D
authors.lastname: Jiang
authors.forename: Simone
authors.initials: S
authors.lastname: Budow
authors.forename: Virginie
authors.initials: V
authors.lastname: Glaçon
authors.forename: Henning
authors.initials: H
authors.lastname: Eickmeier
authors.forename: Hans
authors.initials: H
authors.lastname: Reuter
authors.forename: Yang
authors.initials: Y
authors.lastname: He
authors.forename: Frank
authors.initials: F
authors.lastname: Seela
mesh_terms: D018360:Crystallography, X-Ray; D003849:Deoxyguanosine / Q000031:analogs & derivatives* / Q000737:chemistry*; D006571:Heterocyclic Compounds / Q000737:chemistry*; D006860:Hydrogen Bonding; D008968:Molecular Conformation; D015394:Molecular Structure; D012996:Solutions / Q000737:chemistry; D012997:Solvents / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: C549894:2-amino-8-(2-deoxy-2-fluoroarabinofuranosyl)imidazo(1,2-a)(1,3,5)triazin-4(8H)-one; D006571:Heterocyclic Compounds; D012996:Solutions; D012997:Solvents; D003849:Deoxyguanosine