Chemo-enzymatic synthesis of fluorinated 2-N-acetamidosugar nucleotides using UDP-GlcNAc pyrophosphorylase

Abstract

Two non-natural fluorinated 2-N-acetamidosugar nucleotides, uridine 5′-diphosphate (UDP) 2-acetamido-2,4-dideoxy-4-fluoro-α-D-glucopyranose (UDP-4-FGlcNAc) 1 and its galacto isomer (UDP-4-FGalNAc) 2, were enzymatically constructed by treating chemically synthesized fluorinated 2-N-acetamidosugar 1-phosphates as the donor with UDP 2-acetamido-2-deoxy-α-D-glucopyranose pyrophosphorylase in the presence of uridine 5′-triphosphate (UTP).