ArticleJournal of bacteriology2001
Halohydrin dehalogenases are structurally and mechanistically related to short-chain dehydrogenases/reductases.
Article in Journal of bacteriology, 2001. 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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Who cites it
29 citing papers in PubMed, 175 citations in OpenAlex.
- Engineered halohydrin dehalogenase mediates remote enantiocontrolled dehalogenative hydroxylation via an unconventional mechanism.Nature communications · 2026Article
- Microbially-mediated halogenation and dehalogenation cycling of organohalides in the ocean.Nature communications · 2025Article
- Biocatalytic kinetic resolution for efficient and enantioselective synthesis of δ-haloalcohols and tetrahydrofurans.Communications chemistry · 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
- Community-integrated multi-omics facilitates screening and isolation of the organohalide dehalogenation microorganism.Innovation (Cambridge (Mass.)) · 2023Article
- G-type Halohydrin Dehalogenases Catalyze Ring Opening Reactions of Cyclic Epoxides with Diverse Anionic Nucleophiles.Chemistry (Weinheim an der Bergstrasse, Germany) · 2022Article
- Regiodivergent and stereoselective hydroxyazidation of alkenes by biocatalytic cascades.iScience · 2021Article
- Highly α-position regioselective ring-opening of epoxides catalyzed by halohydrin dehalogenase fromRSC advances · 2019Article
- 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
- Effect of ZnBioengineered · 2017Article
- Combinatorial metabolic engineering of Pseudomonas putida KT2440 for efficient mineralization of 1,2,3-trichloropropane.Scientific reports · 2017Article
- 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
- Exacerbation of substrate toxicity by IPTG in Escherichia coli BL21(DE3) carrying a synthetic metabolic pathway.Microbial cell factories · 2015Article
- Exploring the enantioselective mechanism of halohydrin dehalogenase from Agrobacterium radiobacter AD1 by iterative saturation mutagenesis.Applied and environmental microbiology · 2015Article
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Authors and funding
9 authors at 1 institution in 2 countries.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Halohydrin dehalogenases, also known as haloalcohol dehalogenases or halohydrin hydrogen-halide lyases, catalyze the nucleophilic displacement of a halogen by a vicinal hydroxyl function in halohydrins to yield epoxides. Three novel bacterial genes encoding halohydrin dehalogenases were cloned and expressed in Escherichia coli, and the enzymes were shown to display remarkable differences in substrate specificity. The halohydrin dehalogenase of Agrobacterium radiobacter strain AD1, designated HheC, was purified to homogeneity. The k(cat) and K(m) values of this 28-kDa protein with 1,3-dichloro-2-propanol were 37 s(-1) and 0.010 mM, respectively. A sequence homology search as well as secondary and tertiary structure predictions indicated that the halohydrin dehalogenases are structurally similar to proteins belonging to the family of short-chain dehydrogenases/reductases (SDRs). Moreover, catalytically important serine and tyrosine residues that are highly conserved in the SDR family are also present in HheC and other halohydrin dehalogenases. The third essential catalytic residue in the SDR family, a lysine, is replaced by an arginine in halohydrin dehalogenases. A site-directed mutagenesis study, with HheC as a model enzyme, supports a mechanism for halohydrin dehalogenases in which the conserved Tyr145 acts as a catalytic base and Ser132 is involved in substrate binding. The primary role of Arg149 may be lowering of the pK(a) of Tyr145, which abstracts a proton from the substrate hydroxyl group to increase its nucleophilicity for displacement of the neighboring halide. The proposed mechanism is fundamentally different from that of the well-studied hydrolytic dehalogenases, since it does not involve a covalent enzyme-substrate intermediate.
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