Rates of formation of anhydronucleosides and comparison with their corresponding oxy analogues
Abstract:
Anhydronucleosides are reactive intermediates in the synthesis of modified nucleosides. Their rates of cyclization of 2,2'; 2,3' and 2,5'-anhydro 2-thiouridine were studied and compared with their oxy analogues. The order of displacement of the leaving group is as follows: 2' > 5' > 3'. It was also observed that the rates of cyclization onto the 5' or 3'-position was about 70 times faster in 2-thiouridine series as compared with the uridine series. Similarly the rate of formation of 2, 2'-anhydronucleoside is nearly 2 orders of the magnitude faster in the case of thionucleosides.
Related Concept Videos
Antiviral Nucleoside Inhibitors
Biosynthesis of Nucleic Acids
Base-Catalyzed Ring-Opening of Epoxides
DNA Base Pairing
Predicting Products: SN1 vs. SN2
With increased substitution on the alkyl halide,...
SN2 Reaction: Kinetics
In a chemical reaction, a relationship exists between the concentration of reactants and the rate at which the reaction proceeds. The study to measure this relationship is known as the kinetics of a chemical reaction. Kinetic studies are used to deduce the rate law of a chemical reaction, which provides information about the species involved during the transition state of the rate-determining step. Thus, kinetic studies help to derive the mechanism of a reaction.


