Studies on enzymatic transglycosylation catalyzed by bacterial Nucleoside deoxyribosyltransferase II and Nucleoside phosphorylase for the synthesis of pyrimidine 2′-Deoxyribonucleosides containing modified heterocyclic base

A comparative analysis of enzymatic transglycosylation reactions catalyzed by Lactobacillus leichmannii NDT II and Escherichia coli PNP in the presence of various glycosyl donors and under different conditions was performed to synthesize modified 2ʹ-deoxynucleosides. Substitution of Escherichia coli PNP with Lactobacillus leichmannii NDT II allowed the synthesis of various deoxynucleosides from different glycosyl donors in 39–100% yields. The replacement of thymidine as a commonly used NDT substrate with 7-Methyl-2′-deoxyguanosine as a novel glycosyl-donor allowed the enzymatic synthesis of 2′-deoxycytidine derivatives and 5-substituted 2′-deoxyuridine derivatives, which is essential for further elaboration of eco-friendly technologies for synthesis of base-modified nucleosides.