Document Detail


BN/CC isosteric compounds as enzyme inhibitors: N- and B-ethyl-1,2-azaborine inhibit ethylbenzene hydroxylation as nonconvertible substrate analogues.
MedLine Citation:
PMID:  23355270     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
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.
Authors:
Daniel H Knack; Jonathan L Marshall; Gregory P Harlow; Agnieszka Dudzik; Maciej Szaleniec; Shih-Yuan Liu; Johann Heider
Publication Detail:
Type:  Journal Article; Research Support, N.I.H., Extramural; Research Support, Non-U.S. Gov't     Date:  2013-01-28
Journal Detail:
Title:  Angewandte Chemie (International ed. in English)     Volume:  52     ISSN:  1521-3773     ISO Abbreviation:  Angew. Chem. Int. Ed. Engl.     Publication Date:  2013 Feb 
Date Detail:
Created Date:  2013-02-20     Completed Date:  2014-01-23     Revised Date:  2014-02-26    
Medline Journal Info:
Nlm Unique ID:  0370543     Medline TA:  Angew Chem Int Ed Engl     Country:  Germany    
Other Details:
Languages:  eng     Pagination:  2599-601     Citation Subset:  IM    
Copyright Information:
Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
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MeSH Terms
Descriptor/Qualifier:
Benzene Derivatives / antagonists & inhibitors,  chemistry*,  metabolism
Boron Compounds / chemistry*,  pharmacology*
Enzyme Inhibitors / chemistry*,  pharmacology*
Hydroxylation / drug effects
Oxidoreductases / antagonists & inhibitors,  chemistry,  metabolism
Grant Support
ID/Acronym/Agency:
R01 GM094541/GM/NIGMS NIH HHS; R01 GM094541/GM/NIGMS NIH HHS
Chemical
Reg. No./Substance:
0/1,2-azaborine; 0/Benzene Derivatives; 0/Boron Compounds; 0/Enzyme Inhibitors; EC 1.-/Oxidoreductases; EC 1.3.-/ethylbenzene dehydrogenase; L5I45M5G0O/ethylbenzene
Comments/Corrections

From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine


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