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bn cc isosteric compounds as enzyme inhibitors n and b ethyl 1 2 azaborine inhibit ethylbenzene hydroxylation as nonconvertible substrate analogues

descriptionPublicationkeyboard_double_arrow_right Article , Other literature type , Journal 28 Jan 2013Publisher:WileyJournal:Angewandte Chemie International Edition, volume 52, pages 2,599-2,601 (issn: 1433-7851, eissn: 1521-3773,

Authors: Jonathan L. Marshall; Daniel H. Knack; Johann Heider; Agnieszka Dudzik; Maciej Szaleniec; Gregory P. Harlow; Shih-Yuan Liu;

doi: 10.1002/anie.201208351

pmid: 23355270

pmc: PMC3748812

bn cc isosteric compounds as enzyme inhibitors n and b ethyl 1 2 azaborine inhibit ethylbenzene hydroxylation as nonconvertible substrate analogues

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Abstract

Good substrate gone bad! BN/CC isosterism of ethylbenzene leads to N-ethyl-1,2-azaborine and B-ethyl-1,2-azaborine. In contrast to ethylbenzene, which is the substrate for ethylbenzene dehydrogenase (EbDH), N-ethyl-1,2-azaborine (see scheme; Fc=Ferricenium tetrafluoroborate) and B-ethyl-1,2-azaborine are strong inhibitors of EbDH. Thus, the changes provided by BN/CC isosterism can lead to new biochemical reactivity.

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Keywords

Boron Compounds, Benzene Derivatives, Enzyme Inhibitors, Hydroxylation, Oxidoreductases, Article

4 Research products, page 1 of 1

A DFT Study of the Modulation of the Antiaromatic and Open‐Shell Character of Dibenzo[a,f]pentalene by Employing Three Strategies: Additional Benzoannulation, BN/CC Isosterism, and Substitution
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Late-stage functionalization of BN-heterocycles
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Effect of BN/CC Isosterism on the Thermodynamics of Surface and Bulk Binding: 1,2-Dihydro-1,2-azaborine vs Benzene
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Diterpenoid alkaloids from aconitum episcopale
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	citations This is an alternative to the "Influence" indicator, which also reflects the overall/total impact of an article in the research community at large, based on the underlying citation network (diachronically).	115
	popularity This indicator reflects the "current" impact/attention (the "hype") of an article in the research community at large, based on the underlying citation network.	Top 10%
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bn cc isosteric compounds as enzyme inhibitors n and b ethyl 1 2 azaborine inhibit ethylbenzene hydroxylation as nonconvertible substrate analogues

bn cc isosteric compounds as enzyme inhibitors n and b ethyl 1 2 azaborine inhibit ethylbenzene hydroxylation as nonconvertible substrate analogues

4 Research products, page 1 of 1

A DFT Study of the Modulation of the Antiaromatic and Open‐Shell Character of Dibenzo[a,f]pentalene by Employing Three Strategies: Additional Benzoannulation, BN/CC Isosterism, and Substitution

Late-stage functionalization of BN-heterocycles

Effect of BN/CC Isosterism on the Thermodynamics of Surface and Bulk Binding: 1,2-Dihydro-1,2-azaborine vs Benzene

Diterpenoid alkaloids from aconitum episcopale