Beilstein J. Org. Chem.2014,10, 1657–1669, doi:10.3762/bjoc.10.173
phosphate 12a: ribokinase (2-deoxy-2-fluoro-D-arabinofuranose-5-phosphate), phosphopentomutase (PPN; no 1,6-diphosphates of D-hexoses as co-factors required) (12a), and finally PNP. The substrate activities of D-arabinose, D-ribose and D-xylose in the similar cascade syntheses of the relevant 2
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; recombinant E. coli ribokinase
demonstrated that D-ribose and 2-deoxy-D-ribose can be converted to nucleosides in the cascade one-pot synthesis under the consecutive action of three E. coli enzymes, i.e., ribokinase (RK), phosphopentomutase (PPM) and nucleoside phosphorylases [24][25][26][27] (for a recent review, see [28]). In the present
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Graphical Abstract
Figure 1:
The structures of purine nucleosides studied in the chemoenzymatic synthesis and in a cascade one-p...