7-Deaza-2'-deoxyinosine: a nucleoside showing ambiguous base-pairing properties against the four canonical DNA constituents.
The title compound [systematic name: 7-(2-deoxy-beta-D-erythro-pentofuranosyl)-3,7-dihydro-4H-pyrrolo[2,3-d]pyrimidin-4-one], C(11)H(13)N(3)O(4), represents an acid-stable derivative of 2'-deoxyinosine. It exhibits an anti glycosylic bond conformation, with a chi torsion angle of 113.30 (15) degrees . The furanose moiety adopts an S-type sugar pucker (4)T(3), with P = 221.8 (1) degrees and tau(m) = 40.4 (1) degrees . The conformation at the exocyclic C4'-C5' bond of the furanose ring is ap (trans), with gamma = 167.14 (10) degrees . The extended structure forms a three-dimensional hydrogen-bond network involving O-H...O, N-H...O and C-H...O hydrogen bonds. The title compound forms an uncommon hydrogen bond between a CH group of the pyrrole system and the ring O atom of the sugar moiety of a neighbouring molecule.
Seela
Frank
F
Laboratorium für Organische und Bioorganische Chemie, Institut für Chemie, Universität Osnabrück, Barbarastrasse 7, 49069 Osnabrück, Germany. frank.seela@uni-osnabrueck.de
Ming
Xin
X
Eickmeier
Henning
H
Reuter
Hans
H
D020029:Base Pairing; D018360:Crystallography, X-Ray; D004247:DNA / Q000737:chemistry*; D006860:Hydrogen Bonding; D007288:Inosine / Q000031:analogs & derivatives* / Q000737:chemistry; D008958:Models, Molecular
C533718:7-deaza-2'-deoxyinosine; D007288:Inosine; D004247:DNA; C012271:deoxyinosine