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Literature summary extracted from

  • Song, F.; Thoden, J.B.; Zhuang, Z.; Latham, J.; Trujillo, M.; Holden, H.M.; Dunaway-Mariano, D.
    The catalytic mechanism of the hotdog-fold enzyme superfamily 4-hydroxybenzoyl-CoA thioesterase from Arthrobacter sp. strain SU (2012), Biochemistry, 51, 7000-7016.
    View publication on PubMedView publication on EuropePMC

Crystallization (Commentary)

EC Number Crystallization (Comment) Organism
3.1.2.23 wild-type and mutant structures in complex with ligands 4-hydroxybenzoyl-CoA or CoA Arthrobacter sp.

Protein Variants

EC Number Protein Variants Comment Organism
3.1.2.23 D31A steady-state kinetic analysis Arthrobacter sp.
3.1.2.23 D31N steady-state kinetic analysis Arthrobacter sp.
3.1.2.23 E73A steady-state kinetic analysis, crystallization data Arthrobacter sp.
3.1.2.23 E73D mutation switches the function of the carboxylate residue from nucleophilic catalysis to base catalysis and thus, the reaction from a two-step process involving a covalent enzyme intermediate to a single-step hydrolysis reaction Arthrobacter sp.
3.1.2.23 E73D steady-state kinetic analysis Arthrobacter sp.
3.1.2.23 E73D/T77A mutant regains most of the catalytic efficiency lost in the E73D single mutant Arthrobacter sp.
3.1.2.23 E73D/T77S steady-state kinetic analysis Arthrobacter sp.
3.1.2.23 E73Q steady-state kinetic analysis, crystallization data Arthrobacter sp.
3.1.2.23 E78A steady-state kinetic analysis Arthrobacter sp.
3.1.2.23 H64A steady-state kinetic analysis, crystallization data Arthrobacter sp.
3.1.2.23 H64Q steady-state kinetic analysis Arthrobacter sp.
3.1.2.23 Q58A steady-state kinetic analysis, crystallization data Arthrobacter sp.
3.1.2.23 Q58D steady-state kinetic analysis Arthrobacter sp.
3.1.2.23 Q58D/E73D NA complete loss of activity Arthrobacter sp.
3.1.2.23 Q58E steady-state kinetic analysis Arthrobacter sp.
3.1.2.23 Q58E/E73A NA complete loss of activity Arthrobacter sp.
3.1.2.23 Q58E/E73Q NA complete loss of activity Arthrobacter sp.
3.1.2.23 R102A steady-state kinetic analysis Arthrobacter sp.
3.1.2.23 R150A steady-state kinetic analysis Arthrobacter sp.
3.1.2.23 S120A steady-state kinetic analysis Arthrobacter sp.
3.1.2.23 T121A steady-state kinetic analysis Arthrobacter sp.
3.1.2.23 T77A configuration of the active site residues is unchanged. The Thr77 side chain is positioned to bind and orient a water molecule for attack at the benzoyl carbonyl carbon of the putative anhydride intermediate Arthrobacter sp.
3.1.2.23 T77A steady-state kinetic analysis, crystallization data Arthrobacter sp.
3.1.2.23 T77D steady-state kinetic analysis Arthrobacter sp.
3.1.2.23 T77S Ser77 is more effective than is the Thr77 at positioning the water for attack at the 4-hydroxybenzoyl carbonyl carbon of the anhydride intermediate Arthrobacter sp.
3.1.2.23 T77S steady-state kinetic analysis, crystallization data Arthrobacter sp.
3.1.2.23 T77V steady-state kinetic analysis Arthrobacter sp.

KM Value [mM]

EC Number KM Value [mM] KM Value Maximum [mM] Substrate Comment Organism Structure
3.1.2.23 0.00038
-
 4-hydroxybenzoyl-CoA mutant T77D, pH 7.5, 25°C Arthrobacter sp.
3.1.2.23 0.00077
-
 4-hydroxybenzoyl-CoA mutant T77S, pH 7.5, 25°C Arthrobacter sp.
3.1.2.23 0.0012
-
 4-hydroxybenzoyl-CoA wild-type, pH 7.5, 25°C Arthrobacter sp.
3.1.2.23 0.0012
-
 4-hydroxybenzoyl-CoA mutant T77A, pH 7.5, 25°C Arthrobacter sp.
3.1.2.23 0.0016
-
 4-hydroxybenzoyl-CoA mutant Q58A, pH 7.5, 25°C Arthrobacter sp.
3.1.2.23 0.0016
-
 4-hydroxybenzoyl-CoA mutant S120A, pH 7.5, 25°C Arthrobacter sp.
3.1.2.23 0.004
-
 4-hydroxybenzoyl-CoA mutant D31A, pH 7.5, 25°C Arthrobacter sp.
3.1.2.23 0.004
-
 4-hydroxybenzoyl-CoA mutant Q58E, pH 7.5, 25°C Arthrobacter sp.
3.1.2.23 0.0046
-
 4-hydroxybenzoyl-CoA mutant E73D/T77A, pH 7.5, 25°C Arthrobacter sp.
3.1.2.23 0.0055
-
 4-hydroxybenzoyl-CoA mutant T77V, pH 7.5, 25°C Arthrobacter sp.
3.1.2.23 0.0061
-
 4-hydroxybenzoyl-CoA mutant T121A, pH 7.5, 25°C Arthrobacter sp.
3.1.2.23 0.0128
-
 4-hydroxybenzoyl-CoA mutant D31N, pH 7.5, 25°C Arthrobacter sp.
3.1.2.23 0.013
-
 4-hydroxybenzoyl-CoA mutant E73D/T77S, pH 7.5, 25°C Arthrobacter sp.
3.1.2.23 0.014
-
 4-hydroxybenzoyl-CoA mutant R102A, pH 7.5, 25°C Arthrobacter sp.
3.1.2.23 0.0142
-
 4-hydroxybenzoyl-CoA mutant E73Q, pH 7.5, 25°C Arthrobacter sp.
3.1.2.23 0.015
-
 4-hydroxybenzoyl-CoA mutant R150A, pH 7.5, 25°C Arthrobacter sp.
3.1.2.23 0.018
-
 4-hydroxybenzoyl-CoA mutant E73D, pH 7.5, 25°C Arthrobacter sp.
3.1.2.23 0.096
-
 4-hydroxybenzoyl-CoA mutant E78A, pH 7.5, 25°C Arthrobacter sp.
3.1.2.23 0.18
-
 4-hydroxybenzoyl-CoA mutant Q58D, pH 7.5, 25°C Arthrobacter sp.
3.1.2.23 0.237
-
 4-hydroxybenzoyl-CoA mutant H64Q, pH 7.5, 25°C Arthrobacter sp.
3.1.2.23 0.51
-
 4-hydroxybenzoyl-CoA mutant H64A, pH 7.5, 25°C Arthrobacter sp.

Organism

EC Number Organism UniProt Comment Textmining
3.1.2.23 Arthrobacter sp. Q04416
-
-
3.1.2.23 Arthrobacter sp. SU / DSM 20407 Q04416
-
-

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
3.1.2.23 4-Hydroxybenzoyl-CoA + H2O
-
 Arthrobacter sp. 4-Hydroxybenzoate + CoA
-
 ?
3.1.2.23 4-Hydroxybenzoyl-CoA + H2O
-
 Arthrobacter sp. SU / DSM 20407 4-Hydroxybenzoate + CoA
-
 ?
3.1.2.23 additional information residue Glu73 functions in nucleophilic catalysis, Gly65 and Gln58 contribute to transition-state stabilization via hydrogen bond formation with the thioester moiety and Thr77 orients the water nucleophile for attack at the 4-hydroxybenzoyl carbon of the enzymeanhydride intermediate. Mutation E73D switches the function of the carboxylate residue from nucleophilic catalysis to base catalysis and thus, the reaction from a two-step process involving a covalent enzyme intermediate to a single-step hydrolysis reaction. The substrate nucleotide unit is bound to the enzyme surface Arthrobacter sp. ?
-
 ?
3.1.2.23 additional information residue Glu73 functions in nucleophilic catalysis, Gly65 and Gln58 contribute to transition-state stabilization via hydrogen bond formation with the thioester moiety and Thr77 orients the water nucleophile for attack at the 4-hydroxybenzoyl carbon of the enzymeanhydride intermediate. Mutation E73D switches the function of the carboxylate residue from nucleophilic catalysis to base catalysis and thus, the reaction from a two-step process involving a covalent enzyme intermediate to a single-step hydrolysis reaction. The substrate nucleotide unit is bound to the enzyme surface Arthrobacter sp. SU / DSM 20407 ?
-
 ?

Turnover Number [1/s]

EC Number Turnover Number Minimum [1/s] Turnover Number Maximum [1/s] Substrate Comment Organism Structure
3.1.2.23 0.0001
-
 4-hydroxybenzoyl-CoA mutant E73A, pH 7.5, 25°C Arthrobacter sp.
3.1.2.23 0.0017
-
 4-hydroxybenzoyl-CoA mutant E73Q, pH 7.5, 25°C Arthrobacter sp.
3.1.2.23 0.0103
-
 4-hydroxybenzoyl-CoA mutant T77D, pH 7.5, 25°C Arthrobacter sp.
3.1.2.23 0.0417
-
 4-hydroxybenzoyl-CoA mutant D31A, pH 7.5, 25°C Arthrobacter sp.
3.1.2.23 0.123
-
 4-hydroxybenzoyl-CoA mutant E73D, pH 7.5, 25°C Arthrobacter sp.
3.1.2.23 0.127
-
 4-hydroxybenzoyl-CoA mutant Q58A, pH 7.5, 25°C Arthrobacter sp.
3.1.2.23 0.129
-
 4-hydroxybenzoyl-CoA mutant E73D/T77S, pH 7.5, 25°C Arthrobacter sp.
3.1.2.23 0.13
-
 4-hydroxybenzoyl-CoA mutant Q58D, pH 7.5, 25°C Arthrobacter sp.
3.1.2.23 0.15
-
 4-hydroxybenzoyl-CoA mutant H64A, pH 7.5, 25°C Arthrobacter sp.
3.1.2.23 0.17
-
 4-hydroxybenzoyl-CoA mutant T77V, pH 7.5, 25°C Arthrobacter sp.
3.1.2.23 0.28
-
 4-hydroxybenzoyl-CoA mutant H64Q, pH 7.5, 25°C Arthrobacter sp.
3.1.2.23 0.364
-
 4-hydroxybenzoyl-CoA mutant Q58E, pH 7.5, 25°C Arthrobacter sp.
3.1.2.23 1.08
-
 4-hydroxybenzoyl-CoA mutant E78A, pH 7.5, 25°C Arthrobacter sp.
3.1.2.23 1.15
-
 4-hydroxybenzoyl-CoA mutant D31N, pH 7.5, 25°C Arthrobacter sp.
3.1.2.23 1.54
-
 4-hydroxybenzoyl-CoA mutant E73D/T77A, pH 7.5, 25°C Arthrobacter sp.
3.1.2.23 2.09
-
 4-hydroxybenzoyl-CoA mutant T77A, pH 7.5, 25°C Arthrobacter sp.
3.1.2.23 2.4
-
 4-hydroxybenzoyl-CoA wild-type, solvent D2O, pH 7.5, 25°C Arthrobacter sp.
3.1.2.23 3.16
-
 4-hydroxybenzoyl-CoA mutant T77S, pH 7.5, 25°C Arthrobacter sp.
3.1.2.23 6.7
-
 4-hydroxybenzoyl-CoA wild-type, pH 7.5, 25°C Arthrobacter sp.
3.1.2.23 9.5
-
 4-hydroxybenzoyl-CoA mutant R150A, pH 7.5, 25°C Arthrobacter sp.
3.1.2.23 9.7
-
 4-hydroxybenzoyl-CoA mutant T121A, pH 7.5, 25°C Arthrobacter sp.
3.1.2.23 10.1
-
 4-hydroxybenzoyl-CoA mutant S120A, pH 7.5, 25°C Arthrobacter sp.
3.1.2.23 99
-
 4-hydroxybenzoyl-CoA mutant R102A, pH 7.5, 25°C Arthrobacter sp.

kcat/KM [mM/s]

EC Number kcat/KM Value [1/mMs-1] kcat/KM Value Maximum [1/mMs-1] Substrate Comment Organism Structure
3.1.2.23 0.12
-
 4-hydroxybenzoyl-CoA mutant E73Q, pH 7.5, 25°C Arthrobacter sp.
3.1.2.23 0.29
-
 4-hydroxybenzoyl-CoA mutant H64A, pH 7.5, 25°C Arthrobacter sp.
3.1.2.23 1.1
-
 4-hydroxybenzoyl-CoA mutant E78A, pH 7.5, 25°C Arthrobacter sp.
3.1.2.23 1.2
-
 4-hydroxybenzoyl-CoA mutant H64Q, pH 7.5, 25°C Arthrobacter sp.
3.1.2.23 6.8
-
 4-hydroxybenzoyl-CoA mutant E73D, pH 7.5, 25°C Arthrobacter sp.
3.1.2.23 10
-
 4-hydroxybenzoyl-CoA mutant D31A, pH 7.5, 25°C Arthrobacter sp.
3.1.2.23 10
-
 4-hydroxybenzoyl-CoA mutant E73D/T77S, pH 7.5, 25°C Arthrobacter sp.
3.1.2.23 27
-
 4-hydroxybenzoyl-CoA mutant T77D, pH 7.5, 25°C Arthrobacter sp.
3.1.2.23 31
-
 4-hydroxybenzoyl-CoA mutant T77V, pH 7.5, 25°C Arthrobacter sp.
3.1.2.23 72
-
 4-hydroxybenzoyl-CoA mutant Q58D, pH 7.5, 25°C Arthrobacter sp.
3.1.2.23 79
-
 4-hydroxybenzoyl-CoA mutant Q58A, pH 7.5, 25°C Arthrobacter sp.
3.1.2.23 90
-
 4-hydroxybenzoyl-CoA mutant D31N, pH 7.5, 25°C Arthrobacter sp.
3.1.2.23 91
-
 4-hydroxybenzoyl-CoA mutant Q58E, pH 7.5, 25°C Arthrobacter sp.
3.1.2.23 340
-
 4-hydroxybenzoyl-CoA mutant E73D/T77A, pH 7.5, 25°C Arthrobacter sp.
3.1.2.23 630
-
 4-hydroxybenzoyl-CoA mutant R150A, pH 7.5, 25°C Arthrobacter sp.
3.1.2.23 710
-
 4-hydroxybenzoyl-CoA mutant R102A, pH 7.5, 25°C Arthrobacter sp.
3.1.2.23 1600
-
 4-hydroxybenzoyl-CoA mutant T121A, pH 7.5, 25°C Arthrobacter sp.
3.1.2.23 1700
-
 4-hydroxybenzoyl-CoA mutant T77A, pH 7.5, 25°C Arthrobacter sp.
3.1.2.23 4100
-
 4-hydroxybenzoyl-CoA mutant T77S, pH 7.5, 25°C Arthrobacter sp.
3.1.2.23 5400
-
 4-hydroxybenzoyl-CoA wild-type, pH 7.5, 25°C Arthrobacter sp.
3.1.2.23 6300
-
 4-hydroxybenzoyl-CoA mutant S120A, pH 7.5, 25°C Arthrobacter sp.