Comparative Analysis of Enzymatic Transglycosylation Using E. coli Nucleoside Phosphorylases: A Synthetic Concept for the Preparation of Purine Modified 2′-Deoxyribonucleosides from Ribonucleosides |
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| Authors: | Mikhail S Drenichev Vladimir E Oslovsky Anastasia A Zenchenko Claudia V Danilova Mikhail A Varga Roman S Esipov Dmitry D Lykoshin Cyril S Alexeev |
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| Affiliation: | 1.Engelhardt Institute of Molecular Biology, Russian Academy of Sciences, Vavilova Str. 32, 119991 Moscow, Russia; (M.S.D.); (V.E.O.); (A.A.Z.); (C.V.D.); (M.A.V.);2.Laboratory of Biopharmaceutical Technologies, Shemyakin-Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences, Ulitsa Miklukho-Maklaya, 16/10, GSP-7, 117997 Moscow, Russia; (R.S.E.); (D.D.L.) |
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| Abstract: | A comparative analysis of the transglycosylation conditions catalyzed by E. coli nucleoside phosphorylases, leading to the formation of 2′-deoxynucleosides, was performed. We demonstrated that maximal yields of 2′-deoxynucleosides, especially modified, can be achieved under small excess of glycosyl-donor (7-methyl-2′-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′-deoxyribonucleosides, starting from the corresponding ribonucleosides. |
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| Keywords: | 7-methyl-2′ deoxyguanosine nucleoside phosphorylase enzymes transglycosylation biologically active nucleosides fluorine benzyladenine kinetin |
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