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Literature summary for 3.1.2.23 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
Search for more literature for 3.1.2.23

Crystallization (Commentary)

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

Protein Variants

Protein Variants Comment Organism
D31A steady-state kinetic analysis Arthrobacter sp.
D31N steady-state kinetic analysis Arthrobacter sp.
E73A steady-state kinetic analysis, crystallization data Arthrobacter sp.
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.
E73D steady-state kinetic analysis Arthrobacter sp.
E73D/T77A mutant regains most of the catalytic efficiency lost in the E73D single mutant Arthrobacter sp.
E73D/T77S steady-state kinetic analysis Arthrobacter sp.
E73Q steady-state kinetic analysis, crystallization data Arthrobacter sp.
E78A steady-state kinetic analysis Arthrobacter sp.
H64A steady-state kinetic analysis, crystallization data Arthrobacter sp.
H64Q steady-state kinetic analysis Arthrobacter sp.
Q58A steady-state kinetic analysis, crystallization data Arthrobacter sp.
Q58D steady-state kinetic analysis Arthrobacter sp.
Q58D/E73D NA complete loss of activity Arthrobacter sp.
Q58E steady-state kinetic analysis Arthrobacter sp.
Q58E/E73A NA complete loss of activity Arthrobacter sp.
Q58E/E73Q NA complete loss of activity Arthrobacter sp.
R102A steady-state kinetic analysis Arthrobacter sp.
R150A steady-state kinetic analysis Arthrobacter sp.
S120A steady-state kinetic analysis Arthrobacter sp.
T121A steady-state kinetic analysis Arthrobacter sp.
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.
T77A steady-state kinetic analysis, crystallization data Arthrobacter sp.
T77D steady-state kinetic analysis Arthrobacter sp.
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.
T77S steady-state kinetic analysis, crystallization data Arthrobacter sp.
T77V steady-state kinetic analysis Arthrobacter sp.

KM Value [mM]

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

Organism

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

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
4-Hydroxybenzoyl-CoA + H2O
-
 Arthrobacter sp. 4-Hydroxybenzoate + CoA
-
 ?
4-Hydroxybenzoyl-CoA + H2O
-
 Arthrobacter sp. SU / DSM 20407 4-Hydroxybenzoate + CoA
-
 ?
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. ?
-
 ?
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]

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

kcat/KM [mM/s]

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