N-Acyl Specificity of Taka-N-acetyl-β-D-glucosaminidase* Studied by Synthetic Substrate Analogs

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Abstract
In order to investigate the N-acyl specificity of Taka-N-acetyl-β-D-glucosaminidase [EC 3.2.1.30], some of p-nitrophenyl 2-acylamino-2-deoxy-B-D-glucopyranosides containing formyl, propionyl, n-butyryl, isobutyryl, and benzoyl groups as N-substituent were synthesized. The substrate analogs other than N-benzoyl derivative were hydrolysed by this enzyme. Thus, the N-acyl specificity of this enzyme was not restricted to N-acetyl group, although it was found to be the most favorable substituent for the enzymatic reaction. The specificity was suggested to be controlled by the steric factor of the substrate N-substituent. In addition, other factors such as a hydrophobic and an electronic factors are also presumed to be concerned. It was confirmed by the enzymic reaction and melting point determination that O-N acetyl migration in N-acylation process did not occur.

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