(Salen)Metal-Catalyzed β-Glucuronidation of Alcohols, Phenols, and Anilines.

ABSTRACT: β-Glucuronidation is an important metabolic pathway for a variety of chemicals, including drugs and endogenous substances. We report here that simple (salen)cobalt and (salen)chromium complexes catalyze the β-glucuronidation of alcohols, phenols, and anilines via stereospecific opening of 1,2-anhydroglucuronate electrophiles. The optimized protocol is mild and pH-neutral, enabling the β-glucuronidation of complex pharmaceuticals and natural products bearing acid-sensitive and Lewis-basic functionalities. Kinetic studies reveal a first-order kinetic dependence on catalyst concentration, which stands in contrast to the (salen)metal-catalyzed opening of simple epoxides where second-order rate dependence on the catalyst has been observed consistently.

SUBMITTER: Beyer PD 

PROVIDER: S-EPMC12516814 | biostudies-literature | 2025 Oct

REPOSITORIES: biostudies-literature