Radical dehalogenation and purine nucleoside phosphorylase E. coli: how does an admixture of 2′′,3′′-anhydroinosinehinder 2-fluoro-cordycepin synthesis was written by Kayushin, Alexey L.; Tokunova, Julia A.; Fateev, Ilja V.; Arnautova, Alexandra O.; Berzina, Maria Ya.; Paramonov, Alexander S.; Lutonina, Olga I.; Dorofeeva, Elena V.; Antonov, Konstantin V.; Esipov, Roman S.; Mikhailopulo, Igor A.; Miroshnikov, Anatoly I.; Konstantinova, Irina D.. And the article was included in Biomolecules in 2021.Reference of 13146-72-0 The following contents are mentioned in the article:
During the preparative synthesis of 2-fluorocordycepin from 2-fluoroadenosine and 3′′-deoxyinosine catalyzed by E. coli purine nucleoside phosphorylase, a slowdown of the reaction and decrease of yield down to 5% were encountered. An unknown nucleoside was found in the reaction mixture and its structure was established. This nucleoside is formed from the admixture of 2′′,3′′-anhydroinosine, a byproduct in the preparation of 3-′′deoxyinosine. Moreover, 2′′,3′′-anhydroinosine forms during radical dehalogenation of 9-(2′′,5′′-di-O-acetyl-3′′-bromo-3′′-deoxyxylofuranosyl)hypoxanthine, a precursor of 3′′-deoxyinosine in chem. synthesis. The products of 2′′,3′′-anhydroinosine hydrolysis inhibit the formation of 1-phospho-3-deoxyribose during the synthesis of 2-fluorocordycepin. The progress of 2′′,3′′-anhydroinosine hydrolysis was investigated. The reactions were performed in D2O instead of H2O; this allowed accumulating intermediate substances in sufficient quantities. Two intermediates were isolated and their structures were confirmed by mass and NMR spectroscopy. A mechanism of 2′′,3′′-anhydroinosine hydrolysis in D2O is fully determined for the first time. This study involved multiple reactions and reactants, such as 9-((2R,3R,5S)-3-Hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-9H-purin-6-ol (cas: 13146-72-0Reference of 13146-72-0).
9-((2R,3R,5S)-3-Hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-9H-purin-6-ol (cas: 13146-72-0) belongs to tetrahydrofuran derivatives. Tetrahydrofurans and furans are important oxygen-containing heterocycles that often exhibit interesting properties for biological applications or applications in the cosmetic industry. It is more basic than diethyl ether and forms stronger complexes with Li+, Mg2+, and boranes. It is a popular solvent for hydroboration reactions and for organometallic compounds such as organolithium and Grignard reagents.Reference of 13146-72-0
13146-72-0;9-((2R,3R,5S)-3-Hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-9H-purin-6-ol;The future of 13146-72-0;New trend of C10H12N4O4 ;function of 13146-72-0