MetaCyc Reaction:

Superclasses: Reactions Classified By Conversion TypeSimple ReactionsChemical Reactions
Reactions Classified By SubstrateSmall-Molecule Reactions

EC Number:,

Enzymes and Genes:

Burkholderia sp. WS: S-2-haloacid dehalogenaseInferred from experiment: l-dex
Xanthobacter autotrophicus: haloacetate dehydrogenaseInferred from experiment: dhlB

The direction shown, i.e. which substrates are on the left and right sides, is in accordance with the direction in which it was curated.

Most BioCyc compounds have been protonated to a reference pH value of 7.3. Please see the PGDB Concepts Guide for more information.

Mass balance status: Balanced.

Enzyme Commission Primary Name for (S)-2-haloacid dehalogenase

Enzyme Commission Synonyms for 2-haloacid dehalogenase[ambiguous], 2-haloacid halidohydrolase [ambiguous][ambiguous], 2-haloalkanoic acid dehalogenase, 2-haloalkanoid acid halidohydrolase, 2-halocarboxylic acid dehalogenase II, DL-2-haloacid dehalogenase[ambiguous], L-2-haloacid dehalogenase, L-DEX

Enzyme Commission Primary Name for 2-haloacid dehalogenase (configuration-inverting)

Enzyme Commission Synonyms for 2-haloalkanoic acid dehalogenase, 2-haloalkanoid acid halidohydrolase, DL-2-haloacid dehalogenase, DL-2-haloacid dehalogenase (inversion of configuration), DL-2-haloacid halidohydrolase (inversion of configuration), DL-DEXi, (R,S)-2-haloacid dehalogenase (configuration-inverting)

Taxonomic Range: Bacteria

Standard Gibbs Free Energy (ΔrG in kcal/mol): -5.2382355Inferred by computational analysis [Latendresse13]

Enzyme Commission Summary for
Acts on acids of short chain lengths, C2 to C4, with inversion of configuration at C-2. [See also EC, (R)-2-haloacid dehalogenase, EC, 2-haloacid dehalogenase (configuration-inverting) and EC, 2-haloacid dehalogenase (configuration-retaining).

Enzyme Commission Summary for
Dehalogenates both (S)- and (R)-2-haloalkanoic acids to the corresponding (R)- and (S)-hydroxyalkanoic acids, respectively, with inversion of configuration at C-2. The enzyme from Pseudomonas sp. 113 acts on 2-haloalkanoic acids whose carbon chain lengths are five or less.

See also EC, (S)-2-haloacid dehalogenase, EC, (R)-2-haloacid dehalogenase, and EC, 2-haloacid dehalogenase (configuration-retaining).

Citations: [Motosugi82, Kohler98, Morsberger91, Diez96, Klages83, Goldman68, Weightman82, Cairns96, Liu94a, HEPPEL48, Motosugi82a]

Gene-Reaction Schematic

Gene-Reaction Schematic

Instance reaction of [a haloacetate + H2O = glycolate + a halide anion + H+] (
i1: chloroacetate + H2O → glycolate + chloride + H+ (

Unification Links: KEGG:R03830, KEGG:R03830

Relationship Links: BRENDA:EC:, BRENDA:EC:, ENZYME:EC:, ENZYME:EC:, IUBMB-ExplorEnz:EC:, IUBMB-ExplorEnz:EC:, UniProt:RELATED-TO:P24069, UniProt:RELATED-TO:P24070, UniProt:RELATED-TO:Q59168, UniProt:RELATED-TO:Q59728


Cairns96: Cairns SS, Cornish A, Cooper RA (1996). "Cloning, sequencing and expression in Escherichia coli of two Rhizobium sp. genes encoding haloalkanoate dehalogenases of opposite stereospecificity." Eur J Biochem 235(3);744-9. PMID: 8654424

Diez96: Diez A, Prieto MI, Alvarez MJ, Bautista JM, Garrido J, Puyet A (1996). "Improved catalytic performance of a 2-haloacid dehalogenase from Azotobacter sp. by ion-exchange immobilisation." Biochem Biophys Res Commun 220(3);828-33. PMID: 8607850

Goldman68: Goldman P, Milne GW, Keister DB (1968). "Carbon-halogen bond cleavage. 3. Studies on bacterial halidohrolases." J Biol Chem 243(2);428-34. PMID: 5635785

HEPPEL48: HEPPEL LA, PORTERFIELD VT (1948). "Enzymatic dehalogenation of certain brominated and chlorinated compounds." J Biol Chem 176(2);763-9. PMID: 18889931

Klages83: Klages U, Krauss S, Lingens F (1983). "2-Haloacid dehalogenase from a 4-chlorobenzoate-degrading Pseudomonas spec. CBS 3." Hoppe Seylers Z Physiol Chem 364(5);529-35. PMID: 6873881

Kohler98: Kohler R, Brokamp A, Schwarze R, Reiting RH, Schmidt FR (1998). "Characteristics and DNA-sequence of a cryptic haloalkanoic acid dehalogenase from Agrobacterium tumefaciens RS5." Curr Microbiol 36(2);96-101. PMID: 9425247

Latendresse13: Latendresse M. (2013). "Computing Gibbs Free Energy of Compounds and Reactions in MetaCyc."

Liu94a: Liu JQ, Kurihara T, Hasan AK, Nardi-Dei V, Koshikawa H, Esaki N, Soda K (1994). "Purification and characterization of thermostable and nonthermostable 2-haloacid dehalogenases with different stereospecificities from Pseudomonas sp. strain YL." Appl Environ Microbiol 60(7);2389-93. PMID: 8074519

Morsberger91: Morsberger FM, Muller R, Otto MK, Lingens F, Kulbe KD (1991). "Purification and characterization of 2-halocarboxylic acid dehalogenase II from Pseudomonas spec. CBS 3." Biol Chem Hoppe Seyler 372(10);915-22. PMID: 1772590

Motosugi82: Motosugi K, Esaki N, Soda K (1982). "Bacterial assimilation of D- and L-2-chloropropionates and occurrence of a new dehalogenase." Arch Microbiol 131(3);179-83. PMID: 7103659

Motosugi82a: Motosugi K, Esaki N, Soda K (1982). "Purification and properties of a new enzyme, DL-2-haloacid dehalogenase, from Pseudomonas sp." J Bacteriol 150(2);522-7. PMID: 7068529

Weightman82: Weightman AJ, Weightman AL, Slater JH (1982). "Stereospecificity of 2-monochloropropionate dehalogenation by the two dehalogenases of Pseudomonas putida PP3: evidence for two different dehalogenation mechanisms." J Gen Microbiol 128(8);1755-62. PMID: 7142958

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Please cite the following article in publications resulting from the use of MetaCyc: Caspi et al, Nucleic Acids Research 42:D459-D471 2014
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