8-Aza-7-deaza-2'-deoxy-2-(methylsulfanyl)adenosine.
In the title compound, 4-amino-1-(2-deoxy-beta-D-erythro-pentofuranosyl)-6-methylsulfanyl-1H-pyrazolo[3,4-d]pyrimidine, C11H16N5O3S, the conformation of the glycosidic bond is between anti and high anti. The 2'-deoxyribofuranosyl moiety adopts the C3'-exo-C4'-endo conformation (3T4, S-type sugar pucker), and the conformation at the exocyclic C-C bond is +sc (+gauche). The exocyclic 6-amine group and the 2-methylsulfanyl group lie on different sides of the heterocyclic ring system. The molecules form a three-dimensional hydrogen-bonded network that is stabilized by O-H...N, N-H...O and C-H...O hydrogen bonds.
Seela
Frank
F
Laboratorium für Organische und Bioorganische Chemie, Institut für Chemie, Universität Osnabrück, Barbarastrasse 7, 49069 Osnabrück, Germany. frank.seela@uni-osnabrueck.de
Jawalekar
Anup M
AM
Budow
Simone
S
Eickmeier
Henning
H
D000241:Adenosine / Q000031:analogs & derivatives* / Q000737:chemistry; D001372:Aza Compounds / Q000737:chemistry*; D006860:Hydrogen Bonding; D008958:Models, Molecular
C515420:8-aza-7-deaza-2'-deoxy-2-(methylsulfanyl)adenosine; D001372:Aza Compounds; D000241:Adenosine