| Autor: |
Stepchenko, Vladimir A., Seela, Frank, Esipov, Roman S., Miroshnikov, Anatoly I., Sokolov, Yuri A., Mikhailopulo, Igor A. |
| Předmět: |
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| Zdroj: |
Synlett; Jul2012, Vol. 23, p1541-1545, 5p |
| Abstrakt: |
The enzymatic synthesis of 8-azapurine and 8-aza-7- deazapurine 2'-deoxyribonucleosides has been studied. Two methods have been used: (i) transglycosylation employing 2'-deoxyguanosine, 2'-deoxycytidine, 2'-deoxyuridine, and 2'-deoxythymidine as 2-deoxy-D-ribofuranose donors and recombinant E. coli purine nucleoside phosphorylase (PNP) as biocatalyst, and (ii) one-pot synthesis from 2-deoxy-D-ribose and nucleobases employing recombinant E. coli ribokinase (RK), phosphopentomutase (PPM) and PNP as biocatalysts. Good substrate activity was observed for all bases studied except 2-amino-8-aza-6-chloro-7-deazapurine, which afforded the desired N9-nucleoside in moderate yield due to very low solubility of the base and partial replacement of C6-chloro atom of the base and formed nucleoside with a hydroxy group. The participation of Ser90 Oγ of E. coli PNP in the binding of 8-aza-7- deazapurines in the catalytic center of PNP followed by the formation of a productive complex and glycosidic bond is suggested. [ABSTRACT FROM AUTHOR] |
| Databáze: |
Complementary Index |
| Externí odkaz: |
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