Bacterial catabolism of biphenyls: Synthesis and evaluation of analogues


A series of alkylated 2,3-dihydroxybiphenyls were prepared on the gram-scale by using an effective directed ortho Metalation-Suzuki-Miyaura cross-coupling strategy. These compounds have been used to investigate the substrate specificity of the meta-cleavage dioxygenase BphC, a key enzyme in the microbial catabolism of biphenyl. Isolation and characterization of the meta-cleavage products will allow further study of related processes, including the catabolism of lignin-derived biphenyls. [on SciFinder(R)]