David Schachter

The chemical estimation of acyl glucuronides and its application to studies on the metabolism of benzoate and salicylate in man.

Structurally, glucuronides are the condensation products of hydroxyl-bearing compounds with the first, hemiacetal carbon of D-glucuronic acid. Two groups have been described (1). Alcohols and phenols form ethereal glucuronides, which are resistant to hydrolysis by mild alkali and do not reduce alkaline copper reagents. Carboxylic acids form ester glucuronides, which are easily split by mild alkali to liberate free glucuronic acid, a reducing agent. The term acyl glucuronide is introduced here for members of the latter group to denote clearly conjugation via the carboxyl group. Another chemical reaction characteristic of the acyl glucuronides is described in this report. At room temperature and neutral pH, the acyl group can be transferred to hydroxylamine to form characteristic hydroxamic acids (Reaction I). acids in man. Since urinary glucuronides have been found following the ingestion of benzoate, salicylate, and probenecid (1, 3), observations were made on the metabolism of these clinically important drugs.