22715-28-2Relevant articles and documents
Kinetics of the Multistage Reactions of 6-Substituted Purine Nucleosides with Aqueous Alkalies
Loennberg, Harri,Kaeppi, Rainer,Lehikoinen, Pertti,Oivanen, Mikko
, p. 34 - 40 (2007/10/02)
Reactions of some 6-substituted 9-(β-D-ribofuranosyl)purines with aqueous sodium hydroxide have been studied by liquid chromatography.The main reaction pathway for the decomposition of 6-chloro, 6-methyl and 6-methylthio derivatives has been shown to consist of three consecutive reactions: an attack of hydroxide ion on C8 atom with rapid subsequent openingof the imidazole ring and anomerization of the glycone moiety, deformylation of the resulting 5-formamido-4-ribosylaminopyrimidines, and clevage of the N-glicosidic bond.With the 6-chloro derivative, the first step is irreversible, while with the 6-methyl and 6-methylthio derivatives, recyclization to purine ribosides competes with the deformylation of 5-formamido-4-ribosylaminopyrimidines. 6-Chloro- and 6-methylthio-9-(β-D-ribofuranosyl)purines also yield some inosine, but this reaction is of minor importance.In contrast, 6-methoxy-9-(β-D-ribofuranosyl)purine is converted quantitatively to inosine.The rate constants for the different partial reactions have been determined at several concentrations of hydroxide ion.The kinetic data, and those reported earlier for adenosine and 9-(β-D-ribofuranosyl)purine, have been used to evaluate the susceptibility of the consecutive steps to the polar nature of the 6-substituent.
