The biochemistry of aromatic amines. The resistance of some o-aminoaryl sulphates to hydrolysis by aryl sulphatases

Abstract

Sulfatase preparations from human urine or Taka diastase hydrolyzed all of a number of aryl sulfates except those with a basic amino group in the ortho position to the ester group. No o-aminoaryl sulfates with pKa values of 4.3 or higher were hydrolyzed, and the rates of hydrolysis of a series of less basic aminophenyl sulfates increased as the basicity of the amino groups decreased. The o-aminophenyl sulfates derived from carcinogenic aromatic amines have relatively strong basic groups and were not hydrolyzed by sulfates. 2-Amino-1-naphthyl sulfate, which was not hydrolyzed by sulfatase, did not inhibit the hydrolysis of 2-hydroxy-4-nltrophenyl sulfate. 2-Amino-1-naphthyl phosphate was hydrolyzed by acid and alkaline phosphatase and 2-amino-l-naphthyl glucosiduronate was hydrolyzed by beta-glucuronidase.