7-Amino-1-(2-deoxy-β-erythro-pentofuranosyl)-1H-1,2,3-triazolo[4,5-d]pyrimidine: an 8-azaadenine nucleoside with the nucleobase in a syn conformation.
The title compound, C(9)H(12)N(6)O(3), shows a syn-glycosylic bond orientation [χ = 64.17 (16)°]. The 2'-deoxyfuranosyl moiety exhibits an unusual C1'-exo-O4'-endo ((1)T(0); S-type) sugar pucker, with P = 111.5 (1)° and τ(m) = 40.3 (1)°. The conformation at the exocyclic C4'-C5' bond is +sc (gauche), with γ = 64.4 (1)°. The two-dimensional hydrogen-bonded network is built from intermolecular N-H...O and O-H...N hydrogen bonds. An intramolecular bifurcated hydrogen bond, with an amino N-H group as hydrogen-bond donor and the ring and hydroxymethyl O atoms of the sugar moiety as acceptors, constrains the overall conformation of the nucleoside.
Institute for Nanobiomedical Technology and Membrane Biology, State Key Laboratory of Biotherapy, West-China Medical School/West-China Hospital, Sichuan University, Chengdu 610041, People's Republic of China.
Dawei
D
Jiang
Yang
Y
He
Simone
S
Budow
Zygmunt
Z
Kazimierczuk
Henning
H
Eickmeier
Hans
H
Reuter
Frank
F
Seela
D000225:Adenine / Q000031:analogs & derivatives* / Q000737:chemistry; D001483:Base Sequence; D018360:Crystallography, X-Ray; D006860:Hydrogen Bonding; D008958:Models, Molecular; D008968:Molecular Conformation; D011741:Pyrimidine Nucleosides / Q000737:chemistry*; D011743:Pyrimidines / Q000737:chemistry*; D014230:Triazoles / Q000737:chemistry*
C554377:7-amino-1-(2-deoxy-beta-erythro-pentofuranosyl)-1H-1,2,3-triazolo(4,5-d)pyrimidine; D011741:Pyrimidine Nucleosides; D011743:Pyrimidines; D014230:Triazoles; D000225:Adenine; C006654:8-azaadenine