ArticleProceedings of the National Academy of Sciences of the United States of America2013
Crystal structure of aldoxime dehydratase and its catalytic mechanism involved in carbon-nitrogen triple-bond synthesis.
Article in Proceedings of the National Academy of Sciences of the United States of America, 2013. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 18 papers.
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18 citing papers in PubMed, 66 citations in OpenAlex.
- Molecular dissection of the Cereibacter sphaeroides spheroidene monooxygenase.The Biochemical journal · 2026Article
- Radical Ring-Opening Reaction of Non-Activated Oximes Catalyzed by Aldoxime Dehydratases.Angewandte Chemie (International ed. in English) · 2025Article
- The Heme Oxygenase-Like Diiron Enzyme HrmI Reveals Altered Regulatory Mechanisms for Dioxygen Activation and Substrate N-Oxygenation.Journal of the American Chemical Society · 2025Article
- A single diiron enzyme catalyses the oxidative rearrangement of tryptophan to indole nitrile.Nature chemistry · 2024Article
- Aldoxime dehydratases: production, immobilization, and use in multistep processes.Applied microbiology and biotechnology · 2024Review
- Enzymatic properties of a non-classical aldoxime dehydratase capable of producing alkyl and arylalkyl nitriles.Applied microbiology and biotechnology · 2023Article
- Efficient biosynthesis of nucleoside cytokinin angustmycin A containing an unusual sugar system.Nature communications · 2021Article
- Rationalizing the Unprecedented Stereochemistry of an Enzymatic Nitrile Synthesis through a Combined Computational and Experimental Approach.Angewandte Chemie (International ed. in English) · 2021Article
- Protein engineering of the aldoxime dehydratase from Bacillus sp. OxB-1 based on a rational sequence alignment approach.Scientific reports · 2021Article
- Synthetic Processes toward Nitriles without the Use of Cyanide: A Biocatalytic Concept Based on Dehydration of Aldoximes in Water.Chemistry (Weinheim an der Bergstrasse, Germany) · 2021Article
- Effect of Particle Wettability and Particle Concentration on the Enzymatic Dehydration of n-Octanaloxime in Pickering Emulsions.Angewandte Chemie (International ed. in English) · 2021Article
- Biocatalytic production of adiponitrile and related aliphatic linear α,ω-dinitriles.Nature communications · 2018Article
- Amide compound synthesis by adenylation domain of bacillibactin synthetase.The Journal of antibiotics · 2017Article
- New function of aldoxime dehydratase: Redox catalysis and the formation of an unexpected product.PloS one · 2017Article
- Discovery of a sesamin-metabolizing microorganism and a new enzyme.Proceedings of the National Academy of Sciences of the United States of America · 2016Article
- Evolutionary relationships between heme-binding ferredoxin α + β barrels.BMC bioinformatics · 2016Article
- Substrate, product, and cofactor: The extraordinarily flexible relationship between the CDE superfamily and heme.Archives of biochemistry and biophysics · 2015Review
- A new synthetic route to N-benzyl carboxamides through the reverse reaction of N-substituted formamide deformylase.Applied and environmental microbiology · 2014Article
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8 authors at 3 institutions in 1 country.
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Abstract
Aldoxime dehydratase (OxdA), which is a unique heme protein, catalyzes the dehydration of an aldoxime to a nitrile even in the presence of water in the reaction mixture. Unlike the utilization of H(2)O(2) or O(2) as a mediator of catalysis by other heme-containing enzymes (e.g., P450), OxdA is notable for the direct binding of a substrate to the heme iron. Here, we determined the crystal structure of OxdA. We then constructed OxdA mutants in which each of the polar amino acids lying within ∼6 Å of the iron atom of the heme was converted to alanine. Among the purified mutant OxdAs, S219A had completely lost and R178A exhibited a reduction in the activity. Together with this finding, the crystal structural analysis of OxdA and spectroscopic and electrostatic potential analyses of the wild-type and mutant OxdAs suggest that S219 plays a key role in the catalysis, forming a hydrogen bond with the substrate. Based on the spatial arrangement of the OxdA active site and the results of a series of mutagenesis experiments, we propose the detailed catalytic mechanism of general aldoxime dehydratases: (i) S219 stabilizes the hydroxy group of the substrate to increase its basicity; (ii) H320 acts as an acid-base catalyst; and (iii) R178 stabilizes the heme, and would donate a proton to and accept one from H320.
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