Beilstein J. Org. Chem.2014,10, 1657–1669, doi:10.3762/bjoc.10.173
2-chloro-9-(β-D-arabinofuranosyl)adenine (6) in 45 min, the formation of 2-chloro-9-(β-D-xylofuranosyl)adenine (7) proceeded very slowly attaining ca. 8% yield in 48 h.
Keywords: chemoenzymatic synthesis; clofarabine; nucleoside phosphorylases; phosphopentomutase; recombinantE. coliribokinase
using the α-D-pentofuranose-1-phosphates as glycosylating agents. The cascade synthesis involves a sequential conversion of D-pentoses into their 5-monophosphates catalyzed by the recombinantE. coliribokinase (RK; ATP co-factor) [27], stereospecific isomerization of the 5-phosphates into α-D
D-pentoses into nucleosides of 2-chloroadenine catalyzed by the recombinantE. coliribokinase (RK), phosphopentomutase (PPM) and purine nucleoside phosphorylase (PNP) (purine numbering was used throughout of the manuscript).
The structures of 1-phosphates of α-D-arabinofuranose (13a; AraFur-1P) and
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Graphical Abstract
Figure 1:
The structures of purine nucleosides studied in the chemoenzymatic synthesis and in a cascade one-p...