The 7-bromo derivative of 2-amino-2'-deoxytubercidin fluorinated at the sugar moiety.
The title compound, 2,4-diamino-5-bromo-7-(2-deoxy-2-fluoro-beta-D-arabinofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine, C(11)H(13)BrFN(5)O(3), shows two conformations of the exocyclic C4'-C5' bond, with the torsion angle gamma (O5'-C5'-C4'-C3') being 170.1 (3) degrees for conformer 1 (occupancy 0.69) and 60.7 (7) degrees for conformer 2 (occupancy 0.31). The N-glycosylic bond exhibits an anti conformation, with chi = -114.8 (4) degrees . The sugar pucker is N-type (C3'-endo; (3)T(4)), with P = 23.3 (4) degrees and tau(m) = 36.5 (2) degrees . The compound forms a three-dimensional network that is stabilized by several intermolecular hydrogen bonds (N-H...O, O-H...N and N-H...Br).
Seela
Frank
F
Laboratorium für Organische und Bioorganische Chemie, Institut für Chemie, Universität Osnabrück, Barbarastrasse 7, 49069 Osnabrück, Germany. frank.seela@uni-osnabrueck.de
Ding
Ping
P
Peng
Xiaohua
X
Eickmeier
Henning
H
Reuter
Hans
H
D017605:Bromine Compounds / Q000737:chemistry*; D002241:Carbohydrates / Q000737:chemistry*; D018360:Crystallography, X-Ray; D017611:Fluorine Compounds / Q000737:chemistry*; D006860:Hydrogen Bonding; D008958:Models, Molecular; D015394:Molecular Structure; D011336:Probability; D014372:Tubercidin / Q000031:analogs & derivatives* / Q000737:chemistry*
D017605:Bromine Compounds; D002241:Carbohydrates; D017611:Fluorine Compounds; D014372:Tubercidin