Specific irreversible inhibition of human and boar N-acetyl-β-D-hexosaminidase by 2-acetamido-2-deoxy-β-D-glucopyranosyl isothiocyanate

Abstract 2-Acetamido-2-deoxy-β-D-glucopyranosyl isothiocyanate (I) was obtained by the action of thiophosgene on 2-acetamido-2-deoxy-β-D-glucopyranosylamine. Compound I irreversibly inhibits the human and boar N-acetyl-β-D-hexosaminidase; the dialysis does not restore the enzyme activity. N-Acetyl-D-glucosamine, the competitive inhibitor of N-acetyl-β-D-hexosaminidase, protects the enzyme from inactivation, that testifies to the binding of isothiocyanate I in the active site of the enzyme.