ArticleThe EMBO journal2003
Structure and mechanism of a bacterial haloalcohol dehalogenase: a new variation of the short-chain dehydrogenase/reductase fold without an NAD(P)H binding site.
Article in The EMBO journal, 2003. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 29 papers.
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29 citing papers in PubMed, 129 citations in OpenAlex.
- Engineered halohydrin dehalogenase mediates remote enantiocontrolled dehalogenative hydroxylation via an unconventional mechanism.Nature communications · 2026Article
- A Thr/Ser-centered phosphate-binding triad of phosphate-binding protein SphX from Synechocystis.Communications biology · 2026Article
- Combination of a UPO-Based Epoxidation With a Subsequent Ring-Opening Reaction for the Synthesis of Amino Alcohols.Chembiochem : a European journal of chemical biology · 2026Article
- Biocatalytic kinetic resolution for efficient and enantioselective synthesis of δ-haloalcohols and tetrahydrofurans.Communications chemistry · 2025Article
- Martini 3 coarse-grained model of enzymes: Framework with validation by all-atom simulations and x-ray diffraction measurements.The Journal of chemical physics · 2025Article
- Engineering of Conserved Sequence Motif 1 Residues in Halohydrin Dehalogenase HheC Simultaneously Enhances Activity, Stability, and Enantioselectivity.ACS catalysis · 2025Article
- Biocatalytic enantioselective formation and ring-opening of oxetanes.Nature communications · 2025Article
- A Dynamic Loop in Halohydrin Dehalogenase HheG Regulates Activity and Enantioselectivity in Epoxide Ring Opening.ACS catalysis · 2024Article
- Preparation of (S)-epichlorohydrin using a novel halohydrin dehalogenase by selective conformation adjustment.Biotechnology letters · 2024Article
- Impact of organic solvents on the catalytic performance of halohydrin dehalogenase.Applied microbiology and biotechnology · 2023Article
- Structural Analysis of the Ancestral Haloalkane Dehalogenase AncLinB-DmbA.International journal of molecular sciences · 2021Article
- Position 123 of halohydrin dehalogenase HheG plays an important role in stability, activity, and enantioselectivity.Scientific reports · 2019Article
- Dehalogenases: From Improved Performance to Potential Microbial Dehalogenation Applications.Molecules (Basel, Switzerland) · 2018Review
- Enzymatic Halogenation and Dehalogenation Reactions: Pervasive and Mechanistically Diverse.Chemical reviews · 2017Review
- Enhancing the biocatalytic manufacture of the key intermediate of atorvastatin by focused directed evolution of halohydrin dehalogenase.Scientific reports · 2017Article
- Structures of Proline Utilization A (PutA) Reveal the Fold and Functions of the Aldehyde Dehydrogenase Superfamily Domain of Unknown Function.The Journal of biological chemistry · 2016Article
- Recent advances on halohydrin dehalogenases-from enzyme identification to novel biocatalytic applications.Applied microbiology and biotechnology · 2016Review
- Exploring the enantioselective mechanism of halohydrin dehalogenase from Agrobacterium radiobacter AD1 by iterative saturation mutagenesis.Applied and environmental microbiology · 2015Article
- Expanding the enzyme universe: accessing non-natural reactions by mechanism-guided directed evolution.Angewandte Chemie (International ed. in English) · 2015Review
- Insight into the Mechanism of Intramolecular Inhibition of the Catalytic Activity of Sirtuin 2 (SIRT2).PloS one · 2015Article
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Authors and funding
7 authors at 1 institution in 1 country.
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No grant is acknowledged in the PubMed record.
Abstract
Haloalcohol dehalogenases are bacterial enzymes that catalyze the cofactor-independent dehalogenation of vicinal haloalcohols such as the genotoxic environmental pollutant 1,3-dichloro-2-propanol, thereby producing an epoxide, a chloride ion and a proton. Here we present X-ray structures of the haloalcohol dehalogenase HheC from Agrobacterium radiobacter AD1, and complexes of the enzyme with an epoxide product and chloride ion, and with a bound haloalcohol substrate mimic. These structures support a catalytic mechanism in which Tyr145 of a Ser-Tyr-Arg catalytic triad deprotonates the haloalcohol hydroxyl function to generate an intramolecular nucleophile that substitutes the vicinal halogen. Haloalcohol dehalogenases are related to the widespread family of NAD(P)H-dependent short-chain dehydrogenases/reductases (SDR family), which use a similar Ser-Tyr-Lys/Arg catalytic triad to catalyze reductive or oxidative conversions of various secondary alcohols and ketones. Our results reveal the first structural details of an SDR-related enzyme that catalyzes a substitutive dehalogenation reaction rather than a redox reaction, in which a halide-binding site is found at the location of the NAD(P)H binding site. Structure-based sequence analysis reveals that the various haloalcohol dehalogenases have likely originated from at least two different NAD-binding SDR precursors.
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