Inhibition of in vitro biosynthesis of n-acetylneuraminic acid by n-acyl- and n-alkyl-2-amino-2-deoxyhexoses

The biosynthesis of N-acetylneuraminic acid is markedly inhibited by 2-deoxy-2-propionamido-d-glucose (GlcNProp) and to a much lesser extent by 2-deoxy-2-propionamido-d-mannose (ManNProp), but not by 2-deoxy-2-propionamido-d-galactose and N-methylated derivatives of 2-amino-2-deoxy-d-glucose. 2-Deoxy-2-trimethylamino-d-glucose is a weak inhibitor of 2-acetamido-2-deoxy-d-mannose metabolism. When incubated in a cell-free system from rat liver, GlcNProp gives the 6-phosphate, which is converted into N-propionylneuraminic acid. Evidence is presented which shows that it is the metabolites GlcNProp-6-P and ManNProp-6-P which are the competitive inhibitors, and not GlcNProp itself.