Comparative Analysis of Enzymatic Transglycosylation Using <i>E.</i> <i>coli</i> Nucleoside Phosphorylases: A Synthetic Concept for the Preparation of Purine Modified 2′-Deoxyribonucleosides from Ribonucleosides
A comparative analysis of the transglycosylation conditions catalyzed by <i>E. coli</i> 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...
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MDPI AG
2022-03-01
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| Series: | International Journal of Molecular Sciences |
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| Online Access: | https://www.mdpi.com/1422-0067/23/5/2795 |
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| author | Mikhail S. Drenichev Vladimir E. Oslovsky Anastasia A. Zenchenko Claudia V. Danilova Mikhail A. Varga Roman S. Esipov Dmitry D. Lykoshin Cyril S. Alexeev |
| author_facet | Mikhail S. Drenichev Vladimir E. Oslovsky Anastasia A. Zenchenko Claudia V. Danilova Mikhail A. Varga Roman S. Esipov Dmitry D. Lykoshin Cyril S. Alexeev |
| author_sort | Mikhail S. Drenichev |
| collection | DOAJ |
| description | A comparative analysis of the transglycosylation conditions catalyzed by <i>E. coli</i> 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. |
| first_indexed | 2024-03-09T20:36:51Z |
| format | Article |
| id | doaj.art-4f9fe34fa39c4d2d9d4dace996715f60 |
| institution | Directory Open Access Journal |
| issn | 1661-6596 1422-0067 |
| language | English |
| last_indexed | 2024-03-09T20:36:51Z |
| publishDate | 2022-03-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | International Journal of Molecular Sciences |
| spelling | doaj.art-4f9fe34fa39c4d2d9d4dace996715f602023-11-23T23:09:45ZengMDPI AGInternational Journal of Molecular Sciences1661-65961422-00672022-03-01235279510.3390/ijms23052795Comparative Analysis of Enzymatic Transglycosylation Using <i>E.</i> <i>coli</i> Nucleoside Phosphorylases: A Synthetic Concept for the Preparation of Purine Modified 2′-Deoxyribonucleosides from RibonucleosidesMikhail S. Drenichev0Vladimir E. Oslovsky1Anastasia A. Zenchenko2Claudia V. Danilova3Mikhail A. Varga4Roman S. Esipov5Dmitry D. Lykoshin6Cyril S. Alexeev7Engelhardt Institute of Molecular Biology, Russian Academy of Sciences, Vavilova Str. 32, 119991 Moscow, RussiaEngelhardt Institute of Molecular Biology, Russian Academy of Sciences, Vavilova Str. 32, 119991 Moscow, RussiaEngelhardt Institute of Molecular Biology, Russian Academy of Sciences, Vavilova Str. 32, 119991 Moscow, RussiaEngelhardt Institute of Molecular Biology, Russian Academy of Sciences, Vavilova Str. 32, 119991 Moscow, RussiaEngelhardt Institute of Molecular Biology, Russian Academy of Sciences, Vavilova Str. 32, 119991 Moscow, RussiaLaboratory of Biopharmaceutical Technologies, Shemyakin-Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences, Ulitsa Miklukho-Maklaya, 16/10, GSP-7, 117997 Moscow, RussiaLaboratory of Biopharmaceutical Technologies, Shemyakin-Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences, Ulitsa Miklukho-Maklaya, 16/10, GSP-7, 117997 Moscow, RussiaEngelhardt Institute of Molecular Biology, Russian Academy of Sciences, Vavilova Str. 32, 119991 Moscow, RussiaA comparative analysis of the transglycosylation conditions catalyzed by <i>E. coli</i> 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.https://www.mdpi.com/1422-0067/23/5/27957-methyl-2′deoxyguanosinenucleoside phosphorylaseenzymestransglycosylationbiologically active nucleosidesfluorine |
| spellingShingle | Mikhail S. Drenichev Vladimir E. Oslovsky Anastasia A. Zenchenko Claudia V. Danilova Mikhail A. Varga Roman S. Esipov Dmitry D. Lykoshin Cyril S. Alexeev Comparative Analysis of Enzymatic Transglycosylation Using <i>E.</i> <i>coli</i> Nucleoside Phosphorylases: A Synthetic Concept for the Preparation of Purine Modified 2′-Deoxyribonucleosides from Ribonucleosides International Journal of Molecular Sciences 7-methyl-2′deoxyguanosine nucleoside phosphorylase enzymes transglycosylation biologically active nucleosides fluorine |
| title | Comparative Analysis of Enzymatic Transglycosylation Using <i>E.</i> <i>coli</i> Nucleoside Phosphorylases: A Synthetic Concept for the Preparation of Purine Modified 2′-Deoxyribonucleosides from Ribonucleosides |
| title_full | Comparative Analysis of Enzymatic Transglycosylation Using <i>E.</i> <i>coli</i> Nucleoside Phosphorylases: A Synthetic Concept for the Preparation of Purine Modified 2′-Deoxyribonucleosides from Ribonucleosides |
| title_fullStr | Comparative Analysis of Enzymatic Transglycosylation Using <i>E.</i> <i>coli</i> Nucleoside Phosphorylases: A Synthetic Concept for the Preparation of Purine Modified 2′-Deoxyribonucleosides from Ribonucleosides |
| title_full_unstemmed | Comparative Analysis of Enzymatic Transglycosylation Using <i>E.</i> <i>coli</i> Nucleoside Phosphorylases: A Synthetic Concept for the Preparation of Purine Modified 2′-Deoxyribonucleosides from Ribonucleosides |
| title_short | Comparative Analysis of Enzymatic Transglycosylation Using <i>E.</i> <i>coli</i> Nucleoside Phosphorylases: A Synthetic Concept for the Preparation of Purine Modified 2′-Deoxyribonucleosides from Ribonucleosides |
| title_sort | comparative analysis of enzymatic transglycosylation using i e i i coli i nucleoside phosphorylases a synthetic concept for the preparation of purine modified 2 deoxyribonucleosides from ribonucleosides |
| topic | 7-methyl-2′deoxyguanosine nucleoside phosphorylase enzymes transglycosylation biologically active nucleosides fluorine |
| url | https://www.mdpi.com/1422-0067/23/5/2795 |
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