Bacterial Catabolism of Biphenyls: Synthesis and Evaluation of Analogues

Sven Nerdinger; Eugene Kuatsjah; Timothy E Hurst; Inge Schlapp-Hackl; Volker Kahlenberg; Klaus Wurst; Lindsay D Eltis; Victor Snieckus

doi:10.1002/cbic.201800231

Bacterial Catabolism of Biphenyls: Synthesis and Evaluation of Analogues

Chembiochem. 2018 Jun 15. doi: 10.1002/cbic.201800231. Online ahead of print.

Authors

Sven Nerdinger¹, Eugene Kuatsjah², Timothy E Hurst³, Inge Schlapp-Hackl⁴, Volker Kahlenberg⁵, Klaus Wurst⁶, Lindsay D Eltis², Victor Snieckus³

Affiliations

¹ Global Commercial Operations, Sandoz GmbH, Biochemiestrasse 10, 6250, Kundl, Austria.
² Life Sciences Centre, 2350 Health Sciences Mall, Vancouver, BC, V6T 1Z3, Canada.
³ Department of Chemistry, Queen's University, Chernoff Hall, Kingston, ON, K7L 3N6, Canada.
⁴ Institute of General, Inorganic and Theoretical Chemistry, University of Innsbruck, Center for Chemistry and Biomedicine, Innrain 80-82, 6020, Innsbruck, Austria.
⁵ Institute of Mineralogy and Petrography, University of Innsbruck, Innrain 52, 6020, Innsbruck, Austria.
⁶ Faculty of Chemistry and Pharmacy, University of Innsbruck, Innrain 80-82, 6020, Innsbruck, Austria.

PMID: 29905982
DOI: 10.1002/cbic.201800231

Abstract

A series of alkylated 2,3-dihydroxybiphenyls has been 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.

Keywords: biphenyls; cross-coupling; metalation; microbial catabolism; substrate specificity.