ArticleJournal of the American Chemical Society2014
The active site sulfenic acid ligand in nitrile hydratases can function as a nucleophile.
Article in Journal of the American Chemical Society, 2014. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 22 papers.
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22 citing papers in PubMed, 63 citations in OpenAlex.
- Merging enzymes with chemocatalysis for amide bond synthesis.Nature communications · 2022Article
- Identification of an Intermediate Species along the Nitrile Hydratase Reaction Pathway by EPR Spectroscopy.Biochemistry · 2021Article
- Biodegradation of flonicamid by Ensifer adhaerens CGMCC 6315 and enzymatic characterization of the nitrile hydratases involved.Microbial cell factories · 2021Article
- Maturation Mechanism of Nitrile Hydratase FromFrontiers in microbiology · 2020Article
- Recent Advances and Promises in Nitrile Hydratase: From Mechanism to Industrial Applications.Frontiers in bioengineering and biotechnology · 2020Review
- Cellular maturation of an iron-type nitrile hydratase interrogated using EPR spectroscopy.Journal of biological inorganic chemistry : JBIC : a publication of the Society of Biological Inorganic Chemistry · 2019Article
- Insights into the catalytic mechanism of a bacterial hydrolytic dehalogenase that degrades the fungicide chlorothalonil.The Journal of biological chemistry · 2019Article
- Advances in cloning, structural and bioremediation aspects of nitrile hydratases.Molecular biology reports · 2019Review
- Emergence of metal selectivity and promiscuity in metalloenzymes.Journal of biological inorganic chemistry : JBIC : a publication of the Society of Biological Inorganic Chemistry · 2019Review
- Glutamine-451 Confers Sensitivity to Oxidative Inhibition and Heme-Thiolate Sulfenylation of Cytochrome P450 4B1.Chemical research in toxicology · 2019Article
- Analyzing the function of the insert region found between the α and β-subunits in the eukaryotic nitrile hydratase from Monosiga brevicollis.Archives of biochemistry and biophysics · 2018Article
- Redox Signaling by Reactive Electrophiles and Oxidants.Chemical reviews · 2018Review
- The versatility of boron in biological target engagement.Nature chemistry · 2017Review
- Heme-thiolate sulfenylation of human cytochrome P450 4A11 functions as a redox switch for catalytic inhibition.The Journal of biological chemistry · 2017Article
- Article
- Metal-Assisted Oxo Atom Addition to an Fe(III) Thiolate.Journal of the American Chemical Society · 2017Article
- A Protein-derived Oxygen Is the Source of the Amide Oxygen of Nitrile Hydratases.The Journal of biological chemistry · 2016Article
- Construction of a subunit-fusion nitrile hydratase and discovery of an innovative metal ion transfer pattern.Scientific reports · 2016Article
- Spectroscopic and Computational Studies of Nitrile Hydratase: Insights into Geometric and Electronic Structure and the Mechanism of Amide Synthesis.Chemical science · 2015Article
- Analyzing the catalytic role of active site residues in the Fe-type nitrile hydratase from Comamonas testosteroni Ni1.Journal of biological inorganic chemistry : JBIC : a publication of the Society of Biological Inorganic Chemistry · 2015Article
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5 authors at 3 institutions in 1 country.
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Abstract
Nitrile hydratase (NHase) catalyzes the hydration of nitriles to their corresponding commercially valuable amides at ambient temperatures and physiological pH. Several reaction mechanisms have been proposed for NHase enzymes; however, the source of the nucleophile remains a mystery. Boronic acids have been shown to be potent inhibitors of numerous hydrolytic enzymes due to the open shell of boron, which allows it to expand from a trigonal planar (sp(2)) form to a tetrahedral form (sp(3)). Therefore, we examined the inhibition of the Co-type NHase from Pseudonocardia thermophila JCM 3095 (PtNHase) by boronic acids via kinetics and X-ray crystallography. Both 1-butaneboronic acid (BuBA) and phenylboronic acid (PBA) function as potent competitive inhibitors of PtNHase. X-ray crystal structures for BuBA and PBA complexed to PtNHase were solved and refined at 1.5, 1.6, and 1.2 Å resolution. The resulting PtNHase-boronic acid complexes represent a "snapshot" of reaction intermediates and implicate the cysteine-sulfenic acid ligand as the catalytic nucleophile, a heretofore unknown role for the αCys(113)-OH sulfenic acid ligand. Based on these data, a new mechanism of action for the hydration of nitriles by NHase is presented.
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