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Beilstein J. Org. Chem. 2020, 16, 2607–2622, doi:10.3762/bjoc.16.212
Graphical Abstract
Scheme 1: General scheme of the suggested synthesis of nucleosides employing the enzymatic phosphorolysis of ...
Figure 1: Phosphorolysis (5.0 mM K-phosphate buffer, pH 7.0; 23 °C) of Ara-U and thymidine (Thd) catalyzed by...
Scheme 2: Transarabinosylation of O6-methylguanine (OMG) employing Ara-U as a donor of the Ara-1Pi (1:1.5 mol...
Figure 2: Optimized conditions of phosphorolysis of Ara-U: 0.20 mmol of Ara-U in distilled water (30 mL) cont...
Scheme 3: Synthesis of nelarabine with intermediate preparation of crude Ara-1Pi.
Scheme 4: Synthesis of kinetin riboside with intermediate preparation of crude Rib-1Pi.
Beilstein J. Org. Chem. 2016, 12, 2588–2601, doi:10.3762/bjoc.12.254
Scheme 1: Enzymatic synthesis of 2-deoxy-β-D-ribofuranosides 1b–5b of the heterocyclic bases 1a–5a. Regents a...
Scheme 2: Phosphorolysis of nucleosides 1b–5b and related pyrimidine nucleosides (2’-deoxyuridine, thymidine,...
Figure 1: Phosphorolysis of a number of 2’-deoxy-β-D-ribofuranosides of uracil and thymine, and their 6-aza d...
Figure 2: Phosphorolysis of 2′-deoxyuridine and thymidine, their 4- and 2-thio derivatives and 6-aza-2-thioth...
Figure 3: Supposed monoanionic forms of 4-thiouracil and 2-thiouracil in aqueous medium [48,49].
Figure 4: Phosphorolysis of 6-aza-2-thiothymidine (5b), 4-thiothymidine (11a) and 4-thio-2′-deoxyuridine (1b)...
Figure 5: Structures of 2-thiopyrimidine(9–12) and 5-azacytidine (13 and 14) nucleosides.
Figure 6: Energy minimized structures of N3-(β-D-ribofuranosyl)adenine (left) and 5-aza-2′-deoxycytidine (rig...
Figure 7: Structures of 6-azapyrimidines 15–18 tested for E. coli UP and TP.
Figure 8: Geometry optimized structures (PM3 method) of 5-tert-butyl-6-azauracil (15) and 5-phenyl-6-azauraci...
Figure 9: The UV spectra of 4-thio-2′-deoxyuridine (1b).
Figure 10: The UV spectra of 6-aza-2-thiothymidine (5b).
Beilstein J. Org. Chem. 2014, 10, 1657–1669, doi:10.3762/bjoc.10.173
Figure 1: The structures of purine nucleosides studied in the chemoenzymatic synthesis and in a cascade one-p...
Scheme 1: Chemical synthesis of 2-deoxy-2-fluoro-α/β-D-arabinofuranose-1-phosphates (12a,b). Reagents and con...
Figure 2: The structures of 1-phosphates of α-D-arabinofuranose (13a; AraFur-1P) and β-D-arabinopyranose (13b...
Figure 3: Geometry optimization of 1-phosphates of 2-deoxy-2-fluoro-α-D-arabinofuranose (12a) and the β-anome...
Figure 4: Progress of the formation of 9-(2-deoxy-2-fluoro-β-D-arabinofuranosyl)-2-chloroadenine (1), 2-amino...
Figure 5: Clofarabine content in the reaction mixture vs time (hours) of the reaction.
Scheme 2: Suggested mechanism of purine nucleoside synthesis catalyzed by E. coli purine nucleoside phosphory...
Figure 6: Progress of the formation of β-D-arabinofuranosides and 2-deoxy-2-fluoro-β-D-arabinofuranosides of ...
Figure 7: Tautomeric structures of 5-aza-7-deazaguanine (17).
Figure 8: Progress of the formation of clofarabine (1), 9-(β-D-arabinofuranosyl)-2-chloroadenine (6), 9-(β-D-...