4229-57-6Relevant articles and documents
Enzymatic synthesis of 2-deoxy-β-d-ribonucleosides of 8-azapurines and 8-aza-7-deazapurines
Stepchenko, Vladimir A.,Seela, Frank,Esipov, Roman S.,Miroshnikov, Anatoly I.,Sokolov, Yuri A.,Mikhailopulo, Igor A.
experimental part, p. 1541 - 1545 (2012/09/08)
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. Georg Thieme Verlag Stuttgart · New York.
Enhancement of nucleoside cytotoxicity through nucleotide prodrugs
Rose, Jerry D.,Parker, William B.,Someya, Hitoshi,Shaddix, Sue C.,Montgomery, John A.,Secrist III, John A.
, p. 4505 - 4512 (2007/10/03)
A common reason for the lack of cytotoxicity of certain nucleosides is thought to be their inability to be initially activated to the monophosphate level by a nucleoside kinase or other activating enzyme. In a search for other nucleosides that might be wo
Synthesis of 8-aza-2'-deoxyadenosine and related 7-amino-3H-1,2,3-triazolo[4,5-d]pyrimidine 2'-deoxyribofuranosides: Stereoselective glycosylation via the nucleobase anion
Kazimierczuk,Binding,Seela
, p. 1527 - 1536 (2007/10/02)
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