A fluorogenic substrate for the continuous assaying of aryl sulfatases.

The most common fluorogenic substrate for assaying aryl sulfatases (ARSs) is 4-methylumbelliferyl sulfate (MUS). However, ARSs operate optimally at pH values that are less than the pK(a) (7.8) of the reaction product of MUS, 4-methylumbelliferone (4-MU).

Synthesis and protection of aryl sulfates using the 2,2,2-trichloroethyl moiety.

[reaction: see text] The 2,2,2-trichloroethyl (TCE) group was utilized as the first protecting group for aryl sulfates. Aryl sulfates, protected with the TCE group, were prepared in high yield by reacting phenols with chlorosulfuric acid TCE ester. Deprotection was accomplished using Pd/C-ammonium formate or with Zn-ammonium formate to give aryl sulfate monoesters in high yield.