Document Detail

New inhibitors of iron-containing nitrile hydratases.
MedLine Citation:
PMID:  11481039     Owner:  NLM     Status:  MEDLINE    
There is growing evidence in the literature emphasizing the significance of the post-translational modification of cysteine thiols to sulfenic acids (SOH), which have been found in a number of proteins. Crystallographic and mass spectrometric evidence has shown the presence of this group in an inactive form of the industrially important enzyme nitrile hydratase (NHase). This oxidized cysteine is unique in that it forms part of the coordination sphere of the low-spin iron III at the active site of the enzyme. The presence of this unstable sulfenic group in the active form of NHase is the subject of some controversy. To try to detect this function in NHase, we have studied the inhibitory effect on nitrile hydration of reagents known to react with sulfenic acids. Two NHases were studied, namely, Rhodococcus rhodochrous R312 NHase and Comamonas testosteroni NI1 NHase, and the reagents used were meta-chlorocarbonyldicyano-phenylhydrazone (m-ClCP), 7-chloro-4-nitrobenzo-2-oxa-1,3-diazole (NBD-Cl), and 2-nitro-5-thiocyanato-benzoic acid (NTBA). Following this approach we report three novel inhibitors of NHases. In addition, we report thiocyanate reagents that can be used to monitor NHase activity spectroscopically.
D Bonnet; J M Stevens; R A de Sousa; M A Sari; D Mansuy; I Artaud
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't    
Journal Detail:
Title:  Journal of biochemistry     Volume:  130     ISSN:  0021-924X     ISO Abbreviation:  J. Biochem.     Publication Date:  2001 Aug 
Date Detail:
Created Date:  2001-08-01     Completed Date:  2001-12-18     Revised Date:  2007-12-19    
Medline Journal Info:
Nlm Unique ID:  0376600     Medline TA:  J Biochem     Country:  Japan    
Other Details:
Languages:  eng     Pagination:  227-33     Citation Subset:  IM    
Laboratoire de Chimie et Biochimie Pharmacologiques et Toxicologiques (UMR CNRS), Université Paris V, rue des Saints-Pères, 75270 Paris Cedex 06, France.
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MeSH Terms
4-Chloro-7-nitrobenzofurazan / metabolism,  pharmacology*
Catalytic Domain
Enzyme Inhibitors / metabolism,  pharmacology*
Hydrazones / metabolism,  pharmacology
Hydro-Lyases / antagonists & inhibitors*,  chemistry,  metabolism
Iron / metabolism*
Molecular Structure
Spectrum Analysis
Sulfenic Acids / metabolism*
Thiocyanates / metabolism,  pharmacology*
Reg. No./Substance:
0/Enzyme Inhibitors; 0/Hydrazones; 0/Sulfenic Acids; 0/Thiocyanates; 10199-89-0/4-Chloro-7-nitrobenzofurazan; 14046-96-9/carbonyl 3-chlorophenylhydrazone; 30211-77-9/2-nitro-5-thiocyanobenzoic acid; 7439-89-6/Iron; EC 4.2.1.-/Hydro-Lyases; EC 4.2.1.-/nitrile hydratase

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