Bacterial Catabolism of Biphenyls: Synthesis and Evaluation of Analogues

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...

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Published in:Chembiochem : a European journal of chemical biology 2018-08, Vol.19 (16), p.1771-1778
Main Authors: Nerdinger, Sven, Kuatsjah, Eugene, Hurst, Timothy E., Schlapp‐Hackl, Inge, Kahlenberg, Volker, Wurst, Klaus, Eltis, Lindsay D., Snieckus, Victor
Format: Article
Language:English
Subjects:
Alkylation
Biphenyl
biphenyls
Catabolism
Cleavage
Coupling (molecular)
cross-coupling
Dioxygenase
Lignin
metalation
microbial catabolism
Microorganisms
Substrate specificity
Substrates
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cited_by cdi_FETCH-LOGICAL-c4101-cc8b60a209e5c51812d8ace8dae72e64850ac76f6273ac6e64600f502c66ca773
cites cdi_FETCH-LOGICAL-c4101-cc8b60a209e5c51812d8ace8dae72e64850ac76f6273ac6e64600f502c66ca773
container_end_page 1778
container_issue 16
container_start_page 1771
container_title Chembiochem : a European journal of chemical biology
container_volume 19
creator Nerdinger, Sven
Kuatsjah, Eugene
Hurst, Timothy E.
Schlapp‐Hackl, Inge
Kahlenberg, Volker
Wurst, Klaus
Eltis, Lindsay D.
Snieckus, Victor
description 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. Alkylated 2,3‐dihydroxybiphenyls (DHBs) have been prepared on the gram scale by using a Directed ortho Metalation–Suzuki–Miyaura coupling strategy. These compounds were used to investigate the substrate specificity of the meta‐cleavage dioxygenase BphC, a key enzyme in the microbial catabolism of biphenyl. Isolation of the meta‐cleavage products will allow further study of the catabolism of lignin‐derived biphenyls.
doi_str_mv 10.1002/cbic.201800231
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source Wiley-Blackwell Read & Publish Collection
subjects Alkylation
Biphenyl
biphenyls
Catabolism
Cleavage
Coupling (molecular)
cross-coupling
Dioxygenase
Lignin
metalation
microbial catabolism
Microorganisms
Substrate specificity
Substrates
title Bacterial Catabolism of Biphenyls: Synthesis and Evaluation of Analogues
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