89435-63-2Relevant academic research and scientific papers
Synthesis of bromophenyl β-D-glucuronides: Hydrophilic precursors of lipophilic standards in the analysis of environmental polychlorinated biphenyls
Tandon, Manju,Kumar, Piyush,Xia, Haiyan,Wang, Lili,Wiebe, Leonard I.
, p. 1042 - 1050 (2006)
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.
