BN/CC isosteric compounds as enzyme inhibitors: N- and B-ethyl-1,2-azaborine inhibit ethylbenzene hydroxylation as nonconvertible substrate analogues

Angew Chem Int Ed Engl. 2013 Feb 25;52(9):2599-601. doi: 10.1002/anie.201208351. Epub 2013 Jan 28.

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.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Benzene Derivatives / antagonists & inhibitors
  • Benzene Derivatives / chemistry*
  • Benzene Derivatives / metabolism
  • Boron Compounds / chemistry*
  • Boron Compounds / pharmacology*
  • Enzyme Inhibitors / chemistry*
  • Enzyme Inhibitors / pharmacology*
  • Hydroxylation / drug effects
  • Oxidoreductases / antagonists & inhibitors
  • Oxidoreductases / chemistry
  • Oxidoreductases / metabolism

Substances

  • 1,2-azaborine
  • Benzene Derivatives
  • Boron Compounds
  • Enzyme Inhibitors
  • Oxidoreductases
  • ethylbenzene dehydrogenase
  • ethylbenzene