Literature DB >> 23355270

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

Daniel H Knack1, Jonathan L Marshall, Gregory P Harlow, Agnieszka Dudzik, Maciej Szaleniec, Shih-Yuan Liu, Johann Heider.   

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.
Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

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Year:  2013        PMID： 23355270      PMCID： PMC3748812          DOI： 10.1002/anie.201208351

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN： 1433-7851            Impact factor:   15.336


  15 in total

1.  Ab initio modeling of ethylbenzene dehydrogenase reaction mechanism.

Authors:  Maciej Szaleniec; Tomasz Borowski; Karola Schühle; Malgorzata Witko; Johann Heider
Journal:  J Am Chem Soc       Date:  2010-05-05       Impact factor: 15.419

2.  Resonance stabilization energy of 1,2-azaborines: a quantitative experimental study by reaction calorimetry.

Authors:  Patrick G Campbell; Eric R Abbey; Doinita Neiner; Daniel J Grant; David A Dixon; Shih-Yuan Liu
Journal:  J Am Chem Soc       Date:  2010-12-08       Impact factor: 15.419

3.  Isolation and characterization of anaerobic ethylbenzene dehydrogenase, a novel Mo-Fe-S enzyme.

Authors:  H A Johnson; D A Pelletier; A M Spormann
Journal:  J Bacteriol       Date:  2001-08       Impact factor: 3.490

4.  Crystal structure of ethylbenzene dehydrogenase from Aromatoleum aromaticum.

Authors:  Daniel P Kloer; Corina Hagel; Johann Heider; Georg E Schulz
Journal:  Structure       Date:  2006-09       Impact factor: 5.006

5.  UV-photoelectron spectroscopy of 1,2- and 1,3-azaborines: a combined experimental and computational electronic structure analysis.

Authors:  Anna Chrostowska; Senmiao Xu; Ashley N Lamm; Audrey Mazière; Christopher D Weber; Alain Dargelos; Patrick Baylère; Alain Graciaa; Shih-Yuan Liu
Journal:  J Am Chem Soc       Date:  2012-06-06       Impact factor: 15.419

6.  In vitro studies on the initial reactions of anaerobic ethylbenzene mineralization.

Authors:  H A Johnson; A M Spormann
Journal:  J Bacteriol       Date:  1999-09       Impact factor: 3.490

7.  Crystal clear structural evidence for electron delocalization in 1,2-dihydro-1,2-azaborines.

Authors:  Eric R Abbey; Lev N Zakharov; Shih-Yuan Liu
Journal:  J Am Chem Soc       Date:  2008-05-14       Impact factor: 15.419

8.  Diversity through isosterism: the case of boron-substituted 1,2-dihydro-1,2-azaborines.

Authors:  Adam J V Marwitz; Eric R Abbey; Jesse T Jenkins; Lev N Zakharov; Shih-Yuan Liu
Journal:  Org Lett       Date:  2007-10-18       Impact factor: 6.005

9.  Elemental isomerism: a boron-nitrogen surrogate for a carbon-carbon double bond increases the chemical diversity of estrogen receptor ligands.

Authors:  Hai-Bing Zhou; Kendall W Nettles; John B Bruning; Younchang Kim; Andrzej Joachimiak; Sanjay Sharma; Kathryn E Carlson; Fabio Stossi; Benita S Katzenellenbogen; Geoffrey L Greene; John A Katzenellenbogen
Journal:  Chem Biol       Date:  2007-06

10.  Kinetics and mechanism of oxygen-independent hydrocarbon hydroxylation by ethylbenzene dehydrogenase.

Authors:  Maciej Szaleniec; Corina Hagel; Maurycy Menke; Pawel Nowak; Malgorzata Witko; Johann Heider
Journal:  Biochemistry       Date:  2007-06-02       Impact factor: 3.162
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  24 in total

1.  Synthesis of 1,2-Azaborines and the Preparation of Their Protein Complexes with T4 Lysozyme Mutants.

Authors:  Hyelee Lee; Shih-Yuan Liu
Journal:  J Vis Exp       Date:  2017-03-25       Impact factor: 1.355

2.  Medicinal Chemistry Profiling of Monocyclic 1,2-Azaborines.

Authors:  Peng Zhao; David O Nettleton; Rajeshri G Karki; Frédéric J Zécri; Shih-Yuan Liu
Journal:  ChemMedChem       Date:  2017-02-21       Impact factor: 3.466

3.  Hydrogen Bonding of 1,2-Azaborines in the Binding Cavity of T4 Lysozyme Mutants: Structures and Thermodynamics.

Authors:  Hyelee Lee; Marcus Fischer; Brian K Shoichet; Shih-Yuan Liu
Journal:  J Am Chem Soc       Date:  2016-09-12       Impact factor: 15.419

4.  Accessing 1,2-Substituted Cyclobutanes through 1,2-Azaborine Photoisomerization.

Authors:  Zachary X Giustra; Xinyu Yang; Min Chen; Holger F Bettinger; Shih-Yuan Liu
Journal:  Angew Chem Int Ed Engl       Date:  2019-11-07       Impact factor: 15.336

5.  Rhodium-catalyzed boron arylation of 1,2-azaborines.

Authors:  Gabriel E Rudebusch; Lev N Zakharov; Shih-Yuan Liu
Journal:  Angew Chem Int Ed Engl       Date:  2013-07-05       Impact factor: 15.336

6.  Boron-substituted 1,3-dihydro-1,3-azaborines: synthesis, structure, and evaluation of aromaticity.

Authors:  Senmiao Xu; Tanya C Mikulas; Lev N Zakharov; David A Dixon; Shih-Yuan Liu
Journal:  Angew Chem Int Ed Engl       Date:  2013-06-07       Impact factor: 15.336

7.  Thermodynamically Controlled, Dynamic Binding of Diols to a 1,2-BN Cyclohexane Derivative.

Authors:  Gregory P Harlow; Lev N Zakharov; Gang Wu; Shih-Yuan Liu
Journal:  Organometallics       Date:  2013       Impact factor: 3.876

8.  A convergent, modular approach to functionalized 2,1-borazaronaphthalenes from 2-aminostyrenes and potassium organotrifluoroborates.

Authors:  Steven R Wisniewski; Courtney L Guenther; O Andreea Argintaru; Gary A Molander
Journal:  J Org Chem       Date:  2013-12-11       Impact factor: 4.354

9.  The Dewar Isomer of 1,2-Dihydro-1,2-azaborinines: Isolation, Fragmentation, and Energy Storage.

Authors:  Klara Edel; Xinyu Yang; Jacob S A Ishibashi; Ashley N Lamm; Cäcilia Maichle-Mössmer; Zachary X Giustra; Shih-Yuan Liu; Holger F Bettinger
Journal:  Angew Chem Int Ed Engl       Date:  2018-03-30       Impact factor: 15.336

10.  Protecting group-free synthesis of 1,2-azaborines: a simple approach to the construction of BN-benzenoids.

Authors:  Eric R Abbey; Ashley N Lamm; Andrew W Baggett; Lev N Zakharov; Shih-Yuan Liu
Journal:  J Am Chem Soc       Date:  2013-08-19       Impact factor: 15.419
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