biostudies-literatureUnknown11(4)Kayushin ALDuring the preparative synthesis of 2-fluorocordycepin from 2-fluoroadenosine and 3'-deoxyinosine catalyzed by <i>E. coli</i> 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-<i>O</i>-acetyl-3'-bromo- -3'-deoxyxylofuranosyl)hypoxanthine, a precursor of 3'-deoxyinosine in chemical synthesis. The products of 2',3'-anhydroinosine hydrolysis inhibit the formation of 1-phospho-3-deoxyribose during the synthesis of 2-fluorocordycepin. The progresBiomolecules539https://www.ebi.ac.uk/biostudies/studies/S-EPMC8067715biostudies-literatureRadical Dehalogenation and Purine Nucleoside Phosphorylase <i>E. coli</i>: How Does an Admixture of 2',3'-Anhydroinosine Hinder 2-fluoro-cordycepin Synthesis.PMC8067715Dorofeeva EVMiroshnikov AILutonina OIFateev IVKayushin ALAntonov KVTokunova JABerzina MYParamonov ASArnautova AOEsipov RSMikhailopulo IAKonstantinova IDfalseRadical Dehalogenation and Purine Nucleoside Phosphorylase <i>E. coli</i>: How Does an Admixture of 2',3'-Anhydroinosine Hinder 2-fluoro-cordycepin Synthesis.During the preparative synthesis of 2-fluorocordycepin from 2-fluoroadenosine and 3'-deoxyinosine catalyzed by <i>E. coli</i> 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-<i>O</i>-acetyl-3'-bromo- -3'-deoxyxylofuranosyl)hypoxanthine, a precursor of 3'-deoxyinosine in chemical synthesis. The products of 2',3'-anhydroinosine hydrolysis inhibit the formation of 1-phospho-3-deoxyribose during the synthesis of 2-fluorocordycepin. The progres2021-01-01T00:00:00Z2021 Apr2026-07-16T06:22:43.326Z2025-05-31T23:33:04.647ZS-EPMC80677153391702510.3390/biom11040539