Molecular orbital studies on the structure of nucleoside analogs. III. Conformation of 3-deazapyrimidine nucleosides.
PCILO computations ahve been carried out on the conformational properties of 3-deazapyrimidine nucleosides namely: 3-deazauridine and 3-deazacytidine. These nucleoside analogs result as a consequence of the replacement of N(3) by a carbon atom and they become nucleoside antibiotics having cytostatic and antiviral properties. Both C(2')-endo and C(3')-endo sugar geometries have been considered and the results indicate that the conformational preferences of these nucleoside antibiotics are very similar to those of their parent nucleosides and more particularly so in the situations that occur in aqueous solutions. The important biological significance of the results has been discussed.
D015092:3-Deazauridine; D000900:Anti-Bacterial Agents; D055598:Chemical Phenomena; D002621:Chemistry; D003562:Cytidine / Q000031:analogs & derivatives*; D006860:Hydrogen Bonding; D008968:Molecular Conformation; D013329:Structure-Activity Relationship; D014529:Uridine / Q000031:analogs & derivatives; D014961:X-Ray Diffraction
D000900:Anti-Bacterial Agents; D015092:3-Deazauridine; C000852:3-deazacytidine; D003562:Cytidine; D014529:Uridine