Comparative Analysis of Enzymatic Transglycosylation Using E. coli Nucleoside Phosphorylases: A Synthetic Concept for the Preparation of Purine Modified 2 '-Deoxyribonucleosides from Ribonucleosides

A comparative analysis of the transglycosylation conditions catalyzed by E. coli nucleoside phosphorylases, leading to the formation of 2 & PRIME;-deoxynucleosides, was performed. We demonstrated that maximal yields of 2 & PRIME;-deoxynucleosides, especially modified, can be achieved under small excess of glycosyl-donor (7-methyl-2 & PRIME;-deoxyguanosine, thymidine) and a 4-fold lack of phosphate. A phosphate concentration less than equimolar one allows using only a slight excess of the carbohydrate residue donor nucleoside to increase the reaction's output. A three-step methodology was elaborated for the preparative synthesis of purine-modified 2 & PRIME;-deoxyribonucleosides, starting from the corresponding ribonucleosides.