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Literature summary for 3.8.1.7 extracted from

  • Luo, L.; Taylor, K.L.; Xiang, H.; Wei, Y.; Zhang, W.; Dunaway-Mariano, D.
    Role of active site binding interactions in 4-chlorobenzoyl-coenzyme A dehalogenase catalysis (2001), Biochemistry, 40, 15684-15692.
    View publication on PubMed
Search for more literature for 3.8.1.7

Cloned(Commentary)

Cloned (Comment) Organism
expression of wild-type and mutant enzymes in Escherichia coli Pseudomonas sp.

Protein Variants

Protein Variants Comment Organism
F64A site-directed mutagenesis, decreased kcat and slightly increased Km compared to the wild-type enzyme Pseudomonas sp.
F64P site-directed mutagenesis, highly decreased kcat compared to the wild-type enzyme, nearly inactive Pseudomonas sp.
G113A site-directed mutagenesis, decreased kcat and increased Km compared to the wild-type enzyme Pseudomonas sp.
R24K site-directed mutagenesis, increased kcat and increased Km compared to the wild-type enzyme Pseudomonas sp.
R24L site-directed mutagenesis, decreased kcat and increased Km compared to the wild-type enzyme Pseudomonas sp.
R257K site-directed mutagenesis, slightly decreased kcat and slightly increased Km compared to the wild-type enzyme Pseudomonas sp.
R257L site-directed mutagenesis, decreased kcat and increased Km compared to the wild-type enzyme Pseudomonas sp.
R67K site-directed mutagenesis, decreased kcat and slightly increased Km compared to the wild-type enzyme Pseudomonas sp.
R67L site-directed mutagenesis, expression in inclusion bodies Pseudomonas sp.

Inhibitors

Inhibitors Comment Organism Structure
3'-AMP weak inhibitor Pseudomonas sp.
3'-dephospho-CoA
-
 Pseudomonas sp.
4-Chlorobenzoate poor inhibitor Pseudomonas sp.
4-chlorobenzoyl-coenzyme A competitive Pseudomonas sp.
4-hydroxybenzoyl-3'-dephospho-CoA competitive Pseudomonas sp.
4-hydroxybenzoyl-CoA competitive Pseudomonas sp.
4-hydroxybenzoyl-dithio-CoA competitive Pseudomonas sp.
4-methylbenzoyl-3'-dephospho-CoA competitive Pseudomonas sp.
4-methylbenzoyl-CoA competitive Pseudomonas sp.
5'-ADP weak inhibitor Pseudomonas sp.
5'-AMP weak inhibitor Pseudomonas sp.
adenosine weak inhibitor Pseudomonas sp.
adenosine 3',5'-bisphosphate weak inhibitor Pseudomonas sp.
ATP weak inhibitor Pseudomonas sp.
CoA feedback inhibition Pseudomonas sp.
diphosphate weak inhibitor Pseudomonas sp.

KM Value [mM]

KM Value [mM] KM Value Maximum [mM] Substrate Comment Organism Structure
additional information
-
 additional information kinetics Pseudomonas sp.
0.0037
-
 4-chlorobenzoyl-CoA wild-type enzyme, pH 7.5, 25°C Pseudomonas sp.
0.0052
-
 4-chlorobenzoyl-CoA mutant F64A, pH 7.5, 25°C Pseudomonas sp.
0.0058
-
 4-chlorobenzoyl-CoA mutant R257K, pH 7.5, 25°C Pseudomonas sp.
0.0069
-
 4-chlorobenzoyl-CoA mutant R67K, pH 7.5, 25°C Pseudomonas sp.
0.014
-
 4-chlorobenzoyl-CoA mutant G113A, pH 7.5, 25°C Pseudomonas sp.
0.02
-
 4-chlorobenzoyl-3'-dephospho-CoA wild-type enzyme, pH 7.5, 25°C Pseudomonas sp.
0.021
-
 4-chlorobenzoyl-CoA mutant R24K, pH 7.5, 25°C Pseudomonas sp.
0.024
-
 4-bromophenacyl-CoA wild-type enzyme, pH 7.5, 25°C Pseudomonas sp.
0.033
-
 4-chlorobenzoyl-dithio-CoA wild-type enzyme, pH 7.5, 25°C Pseudomonas sp.
0.041
-
 4-chlorobenzoyl-CoA mutant R24L, pH 7.5, 25°C Pseudomonas sp.
0.07
-
 4-chlorobenzoyl-CoA mutant R257L, pH 7.5, 25°C Pseudomonas sp.
0.07
-
 4-chlorobenzoyl-pantetheine wild-type enzyme, pH 7.5, 25°C, in presence of 1 mM 5'-ADP Pseudomonas sp.
0.11
-
 4-chlorobenzoyl-CoA mutant G114A, pH 7.5, 25°C Pseudomonas sp.
0.31
-
 4-chlorobenzoyl-epsilon-CoA wild-type enzyme, pH 7.5, 25°C Pseudomonas sp.
0.44
-
 4-chlorobenzoyl-pantetheine phosphate wild-type enzyme, pH 7.5, 25°C Pseudomonas sp.
2
-
 4-chlorobenzoyl-pantetheine above, wild-type enzyme, pH 7.5, 25°C Pseudomonas sp.

Natural Substrates/ Products (Substrates)

Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
4-chlorobenzoyl-CoA + H2O Pseudomonas sp. degradation in soil, pathway overview 4-hydroxybenzoyl-CoA + chloride
-
 ?

Organism

Organism UniProt Comment Textmining
Pseudomonas sp.
-
-
-

Reaction

Reaction Comment Organism Reaction ID
4-chlorobenzoyl-CoA + H2O = 4-hydroxybenzoyl CoA + chloride specific for dehalogenation at the 4-position, can dehalogenate substrates bearing fluorine, chlorine, bromine and iodine in the 4-position, multistep mechanism, attack of Asp145 on the C(4) of the substrates' benzoyl ring to form a Meisenheimer intermediate, followed by expulsion of chloride ion to form an arylated enzyme intermediate, and ester hydrolysis to form 4-hydroxybenzoyl-CoA, active site structure Pseudomonas sp.
a

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
4-bromophenacyl-CoA + H2O
-
 Pseudomonas sp. 4-hydroxyphenacyl-CoA + bromide
-
 ?
4-chlorobenzoyl-3'-dephospho-CoA + H2O
-
 Pseudomonas sp. 4-hydroxybenzoyl-3'-dephospho-CoA + chloride
-
 ?
4-chlorobenzoyl-CoA + H2O
-
 Pseudomonas sp. 4-hydroxybenzoyl-CoA + chloride
-
 ?
4-chlorobenzoyl-CoA + H2O degradation in soil, pathway overview Pseudomonas sp. 4-hydroxybenzoyl-CoA + chloride
-
 ?
4-chlorobenzoyl-dithio-CoA + H2O
-
 Pseudomonas sp. 4-hydroxybenzoyl-dithio-CoA + chloride
-
 ?
4-chlorobenzoyl-epsilon-CoA + H2O
-
 Pseudomonas sp. 4-hydroxybenzoyl-epsilon-CoA + chloride
-
 ?
4-chlorobenzoyl-pantetheine + H2O very low activity Pseudomonas sp. 4-hydroxybenzoyl-pantetheine + chloride
-
 ?
4-chlorobenzoyl-pantetheine phosphate + H2O
-
 Pseudomonas sp. 4-hydroxybenzoyl-pantetheine phosphate + chloride
-
 ?

Synonyms

Synonyms Comment Organism
4-CBA-CoA dehalogenase
-
 Pseudomonas sp.
4-chlorobenzoyl-coenzyme A dehalogenase
-
 Pseudomonas sp.

Temperature Optimum [°C]

Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
25
-
 assay at Pseudomonas sp.

Turnover Number [1/s]

Turnover Number Minimum [1/s] Turnover Number Maximum [1/s] Substrate Comment Organism Structure
0.00001
-
 4-chlorobenzoyl-CoA below, mutant F64P, pH 7.5, 25°C Pseudomonas sp.
0.001
-
 4-chlorobenzoyl-pantetheine about, wild-type enzyme, pH 7.5, 25°C Pseudomonas sp.
0.002
-
 4-chlorobenzoyl-CoA mutant G114A, pH 7.5, 25°C Pseudomonas sp.
0.003
-
 4-chlorobenzoyl-dithio-CoA wild-type enzyme, pH 7.5, 25°C Pseudomonas sp.
0.005
-
 4-chlorobenzoyl-CoA mutant G113A, pH 7.5, 25°C Pseudomonas sp.
0.007
-
 4-chlorobenzoyl-epsilon-CoA wild-type enzyme, pH 7.5, 25°C Pseudomonas sp.
0.03
-
 4-bromophenacyl-CoA wild-type enzyme, pH 7.5, 25°C Pseudomonas sp.
0.03
-
 4-chlorobenzoyl-CoA mutant F64A, pH 7.5, 25°C Pseudomonas sp.
0.051
-
 4-chlorobenzoyl-pantetheine phosphate wild-type enzyme, pH 7.5, 25°C Pseudomonas sp.
0.056
-
 4-chlorobenzoyl-pantetheine wild-type enzyme, pH 7.5, 25°C, in presence of 1 mM 5'-ADP Pseudomonas sp.
0.14
-
 4-chlorobenzoyl-CoA mutant R257L, pH 7.5, 25°C Pseudomonas sp.
0.33
-
 4-chlorobenzoyl-CoA mutant R24L, pH 7.5, 25°C Pseudomonas sp.
0.38
-
 4-chlorobenzoyl-CoA mutant R67K, pH 7.5, 25°C Pseudomonas sp.
0.45
-
 4-chlorobenzoyl-3'-dephospho-CoA wild-type enzyme, pH 7.5, 25°C Pseudomonas sp.
0.55
-
 4-chlorobenzoyl-CoA mutant R257K, pH 7.5, 25°C Pseudomonas sp.
0.6
-
 4-chlorobenzoyl-CoA wild-type enzyme, pH 7.5, 25°C Pseudomonas sp.
0.95
-
 4-chlorobenzoyl-CoA mutant R24K, pH 7.5, 25°C Pseudomonas sp.

pH Optimum

pH Optimum Minimum pH Optimum Maximum Comment Organism
7.5
-
 assay at Pseudomonas sp.

Ki Value [mM]

Ki Value [mM] Ki Value maximum [mM] Inhibitor Comment Organism Structure
0.0017
-
 4-hydroxybenzoyl-CoA mutant R257K, pH 7.5, 25°C Pseudomonas sp.
0.0024
-
 4-hydroxybenzoyl-CoA mutant R24K, pH 7.5, 25°C Pseudomonas sp.
0.0025
-
 4-hydroxybenzoyl-CoA wild-type enzyme, pH 7.5, 25°C Pseudomonas sp.
0.0031
-
 4-methylbenzoyl-CoA mutant R257K, pH 7.5, 25°C Pseudomonas sp.
0.0042
-
 4-methylbenzoyl-CoA wild-type enzyme, pH 7.5, 25°C Pseudomonas sp.
0.0062
-
 4-hydroxybenzoyl-CoA mutant R67K, pH 7.5, 25°C Pseudomonas sp.
0.011
-
 4-methylbenzoyl-CoA mutant R24K, pH 7.5, 25°C Pseudomonas sp.
0.0165
-
 4-hydroxybenzoyl-CoA mutant R24L, pH 7.5, 25°C Pseudomonas sp.
0.019
-
 4-hydroxybenzoyl-CoA mutant R257L, pH 7.5, 25°C Pseudomonas sp.
0.022
-
 4-methylbenzoyl-3'-dephospho-CoA wild-type enzyme, pH 7.5, 25°C Pseudomonas sp.
0.04
-
 4-hydroxybenzoyl-CoA mutant G113A, pH 7.5, 25°C Pseudomonas sp.
0.044
-
 4-methylbenzoyl-CoA mutant G113A, pH 7.5, 25°C Pseudomonas sp.
0.046
-
 4-methylbenzoyl-CoA mutant R24L, pH 7.5, 25°C Pseudomonas sp.
0.05 0.1 4-hydroxybenzoyl-CoA mutant G114A, pH 7.5, 25°C Pseudomonas sp.
0.051
-
 4-methylbenzoyl-CoA mutant R67K, pH 7.5, 25°C Pseudomonas sp.
0.055
-
 4-chlorobenzoyl-coenzyme A wild-type enzyme, pH 7.5, 25°C Pseudomonas sp.
0.069
-
 4-hydroxybenzoyl-dithio-CoA wild-type enzyme, pH 7.5, 25°C Pseudomonas sp.
0.072
-
 4-methylbenzoyl-CoA mutant R257L, pH 7.5, 25°C Pseudomonas sp.
0.09
-
 CoA mutant R257K, pH 7.5, 25°C Pseudomonas sp.
0.14
-
 CoA wild-type enzyme, pH 7.5, 25°C Pseudomonas sp.
0.25
-
 CoA mutant R24K, pH 7.5, 25°C Pseudomonas sp.
0.52
-
 CoA mutant R67K, pH 7.5, 25°C Pseudomonas sp.
0.66
-
 CoA mutant R24L, pH 7.5, 25°C Pseudomonas sp.
0.77
-
 3'-dephospho-CoA wild-type enzyme, pH 7.5, 25°C Pseudomonas sp.
2.4
-
 CoA mutant R257L, pH 7.5, 25°C Pseudomonas sp.
4.2
-
 5'-ADP wild-type enzyme, pH 7.5, 25°C Pseudomonas sp.
21
-
 4-Chlorobenzoate wild-type enzyme, pH 7.5, 25°C Pseudomonas sp.