MetaCyc Reaction:

Superclasses: Reactions Classified By Conversion Type Simple Reactions Chemical Reactions
Reactions Classified By Substrate Small-Molecule Reactions

EC Number: ,

Enzymes and Genes:

Burkholderia sp. WS : S-2-haloacid dehalogenase Inferred from experiment : l-dex
Xanthobacter autotrophicus : haloacetate dehydrogenase Inferred from experiment : dhlB

The reaction direction shown, that is, A + B ↔ C + D versus C + D ↔ A + B, 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, and some reactions have been computationally balanced for hydrogen by adding free protons. 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): -5.2382355 Inferred 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, Liu94d, 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."

Liu94d: 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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