Collect. Czech. Chem. Commun. 2006, 71, 1042-1050

Synthesis of Bromophenyl β-D-Glucuronides: Hydrophilic Precursors of Lipophilic Standards in the Analysis of Environmental Polychlorinated Biphenyls

Manju Tandona, Piyush Kumarb,*, Haiyan Xiaa, Lili Wanga and Leonard I. Wiebea,b

a Faculty of Pharmacy and Pharmaceutical Sciences, University of Alberta, Edmonton, Alberta, Canada T6G 2N8
b Department of Oncologic Imaging, Cross Cancer Institute, 11560 University Avenue, Edmonton, Alberta, Canada T6G 1Z2


A rapid PCB-screening protocol, based on a combination of extraction techniques and instrumental nuclear activation analysis (INAA), required water soluble brominated internal standard that undergoes facile hydrolysis to a lipophilic brominated counterpart. Bromophenyl glucuronic acids 2, 3, 7 were synthesized for this application. Glucuronic acids 2 and 3 were prepared by bromination of phenyl β-D-glucopyranosiduronic acid in 81 and 54%, respectively, whereas compound 7 was prepared by coupling methyl 2,3,4-tri-O-acetyl-α-D-glucopyranosyluronate bromide (5) with 2,4,6-tribromophenol. Incubation with β-glucuronidase indicated that tribromophenyl derivative 7 is an excellent substrate, with near quantitative conversion to tribromophenol within seconds of incubation with the enzyme.

Keywords: Glycosides; Glucuronides; Bromophenyl glucuronic acids; Bromination; PCB analysis standards; Instrumental neutron activation analysis (INAA); Bromobenzenes.

References: 9 live references.