Abstract
4-Deoxy-4-fluoro analogues of 2-acetamido-2-deoxy- d-glucose and 2-acetamido-2-deoxy- d-galactose were synthesized and evaluated as inhibitors of hepatic glycosaminoglycan biosynthesis. 2-Acetamido-1,3,6-tri- O-acetyl-2,4-dideoxy-4-fluoro- d-glucopyranose ( 16) exhibited a reduction of [ 3H]GlcN and [ 35S]SO 4 incorporation into hepatocyte cellular glycosaminoglycans to 12 and 18%, respectively, of the control cells, at 1.0 mM. Similarly, 2-acetamido-1,3,6-tri- O-acetyl-2,4-dideoxy-4-fluoro- d-galactopyranose ( 31) exhibited a reduction of [ 3H]GlcN and [ 35S]SO 4 incorporation to 1 and 9%, respectively, of the control cells, at 1.0 mM. Unlike 16, 31 exhibited a reduction of [ 14C]Leu incorporation into cellular protein to 57% of control cells, at 1.0 mM.
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