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MetaCyc Reaction: 3.8.1.9/3.8.1.10

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

EC Number: 3.8.1.9 , 3.8.1.10

The reaction direction shown, that is, A + B ↔ C + D versus C + D ↔ A + B, is in accordance with the Enzyme Commission system.

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 3.8.1.9: (R)-2-haloacid dehalogenase

Enzyme Commission Synonyms for 3.8.1.9: 2-haloalkanoic acid dehalogenase[ambiguous], 2-haloalkanoid acid halidohydrolase[ambiguous], D-2-haloacid dehalogenase, D-DEX

Enzyme Commission Primary Name for 3.8.1.10: 2-haloacid dehalogenase (configuration-inverting)

Enzyme Commission Synonyms for 3.8.1.10: 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)

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

Enzyme Commission Summary for 3.8.1.9:
Acts on acids of short chain lengths, C(2) to C(4), with inversion

Enzyme Commission Summary for 3.8.1.10:
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 3.8.1.2, (S)-2-haloacid dehalogenase, EC 3.8.1.9, (R)-2-haloacid dehalogenase, and EC 3.8.1.11, 2-haloacid dehalogenase (configuration-retaining).

Citations: [Smith90a, Weightman82, Cairns96, Liu94f, HEPPEL48, Motosugi82, Motosugi82a]

Unification Links: KEGG:R07308 , KEGG:R07308

Relationship Links: BRENDA:EC:3.8.1.9 , BRENDA:EC:3.8.1.10 , ENZYME:EC:3.8.1.9 , ENZYME:EC:3.8.1.10 , IUBMB-ExplorEnz:EC:3.8.1.9 , IUBMB-ExplorEnz:EC:3.8.1.10


References

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

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

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

Liu94f: 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

Motosugi82: 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

Motosugi82a: 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

Smith90a: Smith JM, Harrison K, Colby J (1990). "Purification and characterization of D-2-haloacid dehalogenase from Pseudomonas putida strain AJ1/23." J Gen Microbiol 136(5);881-6. PMID: 2380688

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


Report Errors or Provide Feedback
Please cite the following article in publications resulting from the use of MetaCyc: Caspi et al, Nucleic Acids Research 42:D459-D471 2014
Page generated by SRI International Pathway Tools version 18.5 on Wed Nov 26, 2014, biocyc14.