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Literature summary extracted from

  • Song, F.; Zhuang, Z.; Finci, L.; Dunaway-Mariano, D.; Kniewel, R.; Buglino, J.A.; Solorzano, V.; Wu, J.; Lima, C.D.
    Structure, function, and mechanism of the phenylacetate pathway hot dog-fold thioesterase PaaI (2006), J. Biol. Chem., 281, 11028-11038.
    View publication on PubMed

Crystallization (Commentary)

EC Number Crystallization (Comment) Organism
3.1.2.B5 C-terminal His-tagged enzyme is prepared for crystallization. The N-terminal Met is replaced by Ser-Leu. Crystals of the selenomethionine enzyme are grown in 13% polyethylene glycol, 0.1 M [bis(2-hydroxyethyl)imino]-tris(hydroxymethyl)methane (pH 6.0) and 0.2 M lithium sulfate at 18°C using the hanging drop vapor diffusion method. They are incubated in the presence of 30% glycerol before being flash-frozen in liquid nitrogen. The crystals belong to trigonal space group P3(1)21 with a = b = 69.9 A and c = 117.2 A Escherichia coli

Protein Variants

EC Number Protein Variants Comment Organism
3.1.2.B5 D16A significantly reduced activity Escherichia coli
3.1.2.B5 D61A small but detectable level of catalytic activity Escherichia coli
3.1.2.B5 D75A no activity Aromatoleum evansii
3.1.2.B5 E14A reduced activity Escherichia coli
3.1.2.B5 H52A 1000fold decrease in the kcat/Km is observed with the 4-hydroxyphenylacetyl-CoA, and a 100fold decrease in the kcat/Km value is observed with the 3-hydroxyphenylacetyl-CoA or 3,4-dihydroxyphenylacetyl-CoA Escherichia coli
3.1.2.B5 N15A reduced activity Escherichia coli
3.1.2.B5 N46A significantly reduced activity Escherichia coli
3.1.2.B5 N46Q/D61E no activity Escherichia coli
3.1.2.B5 N60A significantly reduced activity Aromatoleum evansii
3.1.2.B5 N60D significantly reduced activity Aromatoleum evansii

Inhibitors

EC Number Inhibitors Comment Organism Structure
3.1.2.B5 3-hydroxyphenylacyl-CoA
-
 Aromatoleum evansii
3.1.2.B5 4-hydroxyphenylacyl-CoA competitive Aromatoleum evansii

KM Value [mM]

EC Number KM Value [mM] KM Value Maximum [mM] Substrate Comment Organism Structure
3.1.2.B5 0.0086
-
 3,4-dihydroxyphenylacetyl-CoA pH 8.1, 25°C, mutant enzyme N60A Aromatoleum evansii
3.1.2.B5 0.0096
-
 phenylacetyl-CoA pH 8.1, 25°C, wild-type enzyme Escherichia coli
3.1.2.B5 0.016
-
 3,4-dihydroxyphenylacetyl-CoA pH 8.1, 25°C, wild-type enzyme Escherichia coli
3.1.2.B5 0.018
-
 4-hydroxyphenylacetyl-CoA pH 8.1, 25°C, mutant enzyme N15A Escherichia coli
3.1.2.B5 0.021
-
 3-hydroxyphenylacetyl-CoA pH 8.1, 25°C, wild-type enzyme Escherichia coli
3.1.2.B5 0.024
-
 3,4-dihydroxyphenylacetyl-CoA pH 8.1, 25°C, mutant enzyme N46A Escherichia coli
3.1.2.B5 0.028
-
 4-hydroxyphenylacetyl-CoA pH 8.1, 25°C, mutant enzyme H52A Escherichia coli
3.1.2.B5 0.028
-
 3,5-dihydroxyphenylacetyl-CoA pH 8.1, 25°C, wild-type enzyme Aromatoleum evansii
3.1.2.B5 0.032
-
 3-hydroxyphenylacetyl-CoA pH 8.1, 25°C, mutant enzyme H52A Escherichia coli
3.1.2.B5 0.033
-
 3,4-dihydroxyphenylacetyl-CoA pH 8.1, 25°C, mutant enzyme D16A Escherichia coli
3.1.2.B5 0.034
-
 3-hydroxyphenylacetyl-CoA pH 8.1, 25°C, mutant enzyme N15A Escherichia coli
3.1.2.B5 0.035
-
 4-hydroxyphenylacetyl-CoA pH 8.1, 25°C, wild-type enzyme Escherichia coli
3.1.2.B5 0.045
-
 3,4-dihydroxyphenylacetyl-CoA pH 8.1, 25°C, mutant enzyme H52A Escherichia coli
3.1.2.B5 0.047
-
 3,4-dihydroxyphenylacetyl-CoA pH 8.1, 25°C, mutant enzyme N15A Escherichia coli
3.1.2.B5 0.048
-
 3,4-dihydroxyphenylacetyl-CoA pH 8.1, 25°C, mutant enzyme D75A Aromatoleum evansii
3.1.2.B5 0.051
-
 3,4-dihydroxyphenylacetyl-CoA pH 8.1, 25°C, wild-type enzyme Aromatoleum evansii
3.1.2.B5 0.055
-
 3,4-dihydroxyphenylacetyl-CoA pH 8.1, 25°C, mutant enzyme N60D Aromatoleum evansii
3.1.2.B5 0.055
-
 4-hydroxyphenylacetyl-CoA pH 8.1, 25°C, wild-type enzyme Aromatoleum evansii
3.1.2.B5 0.08
-
 3-hydroxyphenylacetyl-CoA pH 8.1, 25°C, mutant enzyme E14A Escherichia coli
3.1.2.B5 0.08
-
 3-hydroxyphenylacetyl-CoA pH 8.1, 25°C, wild-type enzyme Aromatoleum evansii
3.1.2.B5 0.09
-
 3-hydroxyphenylacetyl-CoA pH 8.1, 25°C, mutant enzyme D16A Escherichia coli
3.1.2.B5 0.09
-
 4-hydroxyphenylacetyl-CoA pH 8.1, 25°C, mutant enzyme E14A Escherichia coli
3.1.2.B5 0.13
-
 3,4-dihydroxyphenylacetyl-CoA pH 8.1, 25°C, mutant enzyme E14A Escherichia coli
3.1.2.B5 0.2
-
 3,5-dihydroxyphenylacetyl-CoA pH 8.1, 25°C, wild-type enzyme Escherichia coli
3.1.2.B5 0.23
-
 3-hydroxyphenylacetyl-CoA pH 8.1, 25°C, mutant enzyme N46A Escherichia coli
3.1.2.B5 0.25
-
 4-hydroxyphenylacetyl-CoA pH 8.1, 25°C, mutant enzyme D16A Escherichia coli
3.1.2.B5 0.28
-
 4-hydroxyphenylacetyl-CoA pH 8.1, 25°C, mutant enzyme N46A Escherichia coli
3.1.2.B5 0.39
-
 phenylacetyl-CoA pH 8.1, 25°C, wild-type enzyme Aromatoleum evansii

Molecular Weight [Da]

EC Number Molecular Weight [Da] Molecular Weight Maximum [Da] Comment Organism
3.1.2.B5 16419
-
 4 * 16419, ESI mass spectrometry Aromatoleum evansii
3.1.2.B5 58000
-
 gel filtration Escherichia coli
3.1.2.B5 67000
-
 gel filtration Aromatoleum evansii

Natural Substrates/ Products (Substrates)

EC Number Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
3.1.2.B5 3,4-dihydroxyphenylacetyl-CoA + H2O Escherichia coli the enzyme can liberate CoA from phenylacetyl-CoA and from hydroxyphenylacetyl-CoA substrates that are formed in the phenylacetate pathway 3,4-dihydroxyphenylacetate + CoA
-
 ?
3.1.2.B5 3,4-dihydroxyphenylacetyl-CoA + H2O Aromatoleum evansii the enzyme can liberate CoA from phenylacetyl-CoA and from hydroxyphenylacetyl-CoA substrates that form from the phenylacetate pathway 3,4-dihydroxyphenylacetate + CoA
-
 ?
3.1.2.B5 3,4-dihydroxyphenylacetyl-CoA + H2O Aromatoleum evansii DSM 6898 the enzyme can liberate CoA from phenylacetyl-CoA and from hydroxyphenylacetyl-CoA substrates that form from the phenylacetate pathway 3,4-dihydroxyphenylacetate + CoA
-
 ?

Organism

EC Number Organism UniProt Comment Textmining
3.1.2.B5 Aromatoleum evansii Q9F9V0
-
-
3.1.2.B5 Aromatoleum evansii DSM 6898 Q9F9V0
-
-
3.1.2.B5 Escherichia coli P76084
-
-

Storage Stability

EC Number Storage Stability Organism
3.1.2.B5 -80°C, stable for storage in 10 mM K+/Hepes buffer (pH 7.5) or in 10 mM Tris buffer (pH 8.1) containing 10 mM KCl for several months Aromatoleum evansii
3.1.2.B5 0°C, pH 8.1, stored in 10 mM Tris buffer for several weeks without significant loss of activity Escherichia coli

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
3.1.2.B5 3,4-dihydroxyphenylacetyl-CoA + H2O
-
 Escherichia coli 3,4-dihydroxyphenylacetate + CoA
-
 ?
3.1.2.B5 3,4-dihydroxyphenylacetyl-CoA + H2O
-
 Aromatoleum evansii 3,4-dihydroxyphenylacetate + CoA
-
 ?
3.1.2.B5 3,4-dihydroxyphenylacetyl-CoA + H2O the enzyme can liberate CoA from phenylacetyl-CoA and from hydroxyphenylacetyl-CoA substrates that are formed in the phenylacetate pathway Escherichia coli 3,4-dihydroxyphenylacetate + CoA
-
 ?
3.1.2.B5 3,4-dihydroxyphenylacetyl-CoA + H2O the enzyme can liberate CoA from phenylacetyl-CoA and from hydroxyphenylacetyl-CoA substrates that form from the phenylacetate pathway Aromatoleum evansii 3,4-dihydroxyphenylacetate + CoA
-
 ?
3.1.2.B5 3,4-dihydroxyphenylacetyl-CoA + H2O
-
 Aromatoleum evansii DSM 6898 3,4-dihydroxyphenylacetate + CoA
-
 ?
3.1.2.B5 3,4-dihydroxyphenylacetyl-CoA + H2O the enzyme can liberate CoA from phenylacetyl-CoA and from hydroxyphenylacetyl-CoA substrates that form from the phenylacetate pathway Aromatoleum evansii DSM 6898 3,4-dihydroxyphenylacetate + CoA
-
 ?
3.1.2.B5 3,5-dihydroxyphenylacetyl-CoA + H2O
-
 Escherichia coli 3,5-dihydroxyphenylacetate + CoA
-
 ?
3.1.2.B5 3,5-dihydroxyphenylacetyl-CoA + H2O
-
 Aromatoleum evansii 3,5-dihydroxyphenylacetate + CoA
-
 ?
3.1.2.B5 3,5-dihydroxyphenylacetyl-CoA + H2O
-
 Aromatoleum evansii DSM 6898 3,5-dihydroxyphenylacetate + CoA
-
 ?
3.1.2.B5 3-hydroxyphenylacetyl-CoA + H2O
-
 Escherichia coli 3-hydroxyphenylacetate + CoA
-
 ?
3.1.2.B5 3-hydroxyphenylacetyl-CoA + H2O
-
 Aromatoleum evansii 3-hydroxyphenylacetate + CoA
-
 ?
3.1.2.B5 4-hydroxyphenylacetyl-CoA + H2O
-
 Escherichia coli 4-hydroxyphenylacetate + CoA
-
 ?
3.1.2.B5 4-hydroxyphenylacetyl-CoA + H2O
-
 Aromatoleum evansii 4-hydroxyphenylacetate + CoA
-
 ?
3.1.2.B5 additional information no activity with 4-hydroxybenzoyl-CoA, 3-hydroxybenzoyl-CoA, 4-hydroxybenzyl-CoA, 4-hydroxyphenacyl-CoA, 3-hydroxyphenacyl-CoA, 4-chlorobenzoyl-CoA, 4-methoxybenzoyl-CoA. Low activity with acetyl-CoA, n-hexanoyl-CoA, n-butyryl-CoA, isobutyryl-CoA, beta-hydroxybutyryl-CoA, methylmalonyl-CoA, crotonyl-CoA Aromatoleum evansii ?
-
 ?
3.1.2.B5 additional information no activity with 4-hydroxybenzoyl-CoA, 4-hydroxybenzyl-CoA, 4-hydroxyphenacyl-CoA Escherichia coli ?
-
 ?
3.1.2.B5 additional information no activity with 4-hydroxybenzoyl-CoA, 3-hydroxybenzoyl-CoA, 4-hydroxybenzyl-CoA, 4-hydroxyphenacyl-CoA, 3-hydroxyphenacyl-CoA, 4-chlorobenzoyl-CoA, 4-methoxybenzoyl-CoA. Low activity with acetyl-CoA, n-hexanoyl-CoA, n-butyryl-CoA, isobutyryl-CoA, beta-hydroxybutyryl-CoA, methylmalonyl-CoA, crotonyl-CoA Aromatoleum evansii DSM 6898 ?
-
 ?
3.1.2.B5 phenylacetyl-CoA + H2O
-
 Escherichia coli phenylacetate + CoA
-
 ?
3.1.2.B5 phenylacetyl-CoA + H2O
-
 Aromatoleum evansii phenylacetate + CoA
-
 ?
3.1.2.B5 phenylacetyl-CoA + H2O
-
 Aromatoleum evansii DSM 6898 phenylacetate + CoA
-
 ?

Subunits

EC Number Subunits Comment Organism
3.1.2.B5 homotetramer 4 * 16419, ESI mass spectrometry Aromatoleum evansii
3.1.2.B5 homotetramer 4 *14720, ESI mass spectrometry Escherichia coli

Synonyms

EC Number Synonyms Comment Organism
3.1.2.B5 PaaI
-
 Escherichia coli
3.1.2.B5 PaaI
-
 Aromatoleum evansii

Turnover Number [1/s]

EC Number Turnover Number Minimum [1/s] Turnover Number Maximum [1/s] Substrate Comment Organism Structure
3.1.2.B5 0.0065
-
 3,4-dihydroxyphenylacetyl-CoA pH 8.1, 25°C, mutant enzyme D75A Aromatoleum evansii
3.1.2.B5 0.012
-
 3,4-dihydroxyphenylacetyl-CoA pH 8.1, 25°C, mutant enzyme N60A Aromatoleum evansii
3.1.2.B5 0.065
-
 3-hydroxyphenylacetyl-CoA pH 8.1, 25°C, mutant enzyme D16A Escherichia coli
3.1.2.B5 0.076
-
 3,4-dihydroxyphenylacetyl-CoA pH 8.1, 25°C, mutant enzyme N46A Escherichia coli
3.1.2.B5 0.11
-
 3,4-dihydroxyphenylacetyl-CoA pH 8.1, 25°C, mutant enzyme D16A Escherichia coli
3.1.2.B5 0.17
-
 4-hydroxyphenylacetyl-CoA pH 8.1, 25°C, mutant enzyme D16A Escherichia coli
3.1.2.B5 0.18
-
 3,4-dihydroxyphenylacetyl-CoA pH 8.1, 25°C, mutant enzyme N60D Aromatoleum evansii
3.1.2.B5 0.26
-
 4-hydroxyphenylacetyl-CoA pH 8.1, 25°C, mutant enzyme H52A Escherichia coli
3.1.2.B5 0.31
-
 4-hydroxyphenylacetyl-CoA pH 8.1, 25°C, mutant enzyme N46A Escherichia coli
3.1.2.B5 0.41
-
 phenylacetyl-CoA pH 8.1, 25°C, wild-type enzyme Escherichia coli
3.1.2.B5 0.81
-
 3-hydroxyphenylacetyl-CoA pH 8.1, 25°C, mutant enzyme N46A Escherichia coli
3.1.2.B5 0.89
-
 3-hydroxyphenylacetyl-CoA pH 8.1, 25°C, mutant enzyme H52A Escherichia coli
3.1.2.B5 2.3
-
 3,5-dihydroxyphenylacetyl-CoA pH 8.1, 25°C, wild-type enzyme Aromatoleum evansii
3.1.2.B5 2.7
-
 3,4-dihydroxyphenylacetyl-CoA pH 8.1, 25°C, mutant enzyme H52A Escherichia coli
3.1.2.B5 3.2
-
 4-hydroxyphenylacetyl-CoA pH 8.1, 25°C, mutant enzyme N15A Escherichia coli
3.1.2.B5 3.7
-
 phenylacetyl-CoA pH 8.1, 25°C, wild-type enzyme Aromatoleum evansii
3.1.2.B5 8.2
-
 3-hydroxyphenylacetyl-CoA pH 8.1, 25°C, wild-type enzyme Aromatoleum evansii
3.1.2.B5 9
-
 3,5-dihydroxyphenylacetyl-CoA pH 8.1, 25°C, wild-type enzyme Escherichia coli
3.1.2.B5 11
-
 4-hydroxyphenylacetyl-CoA pH 8.1, 25°C, wild-type enzyme Aromatoleum evansii
3.1.2.B5 15
-
 3-hydroxyphenylacetyl-CoA pH 8.1, 25°C, mutant enzyme E14A Escherichia coli
3.1.2.B5 18
-
 3,4-dihydroxyphenylacetyl-CoA pH 8.1, 25°C, wild-type enzyme Aromatoleum evansii
3.1.2.B5 19
-
 4-hydroxyphenylacetyl-CoA pH 8.1, 25°C, mutant enzyme E14A Escherichia coli
3.1.2.B5 20
-
 3,4-dihydroxyphenylacetyl-CoA pH 8.1, 25°C, mutant enzyme E14A Escherichia coli
3.1.2.B5 26
-
 3,4-dihydroxyphenylacetyl-CoA pH 8.1, 25°C, mutant enzyme N15A Escherichia coli
3.1.2.B5 30
-
 3-hydroxyphenylacetyl-CoA pH 8.1, 25°C, mutant enzyme N15A Escherichia coli
3.1.2.B5 79
-
 4-hydroxyphenylacetyl-CoA pH 8.1, 25°C, wild-type enzyme Escherichia coli
3.1.2.B5 86
-
 3-hydroxyphenylacetyl-CoA pH 8.1, 25°C, wild-type enzyme Escherichia coli
3.1.2.B5 100
-
 3,4-dihydroxyphenylacetyl-CoA pH 8.1, 25°C, wild-type enzyme Escherichia coli

Ki Value [mM]

EC Number Ki Value [mM] Ki Value maximum [mM] Inhibitor Comment Organism Structure
3.1.2.B5 0.029
-
 4-hydroxyphenylacyl-CoA pH 8.1, 25°C, wild-type enzyme Aromatoleum evansii
3.1.2.B5 0.039
-
 4-hydroxyphenylacyl-CoA pH 8.1, 25°C, wild-type enzyme Aromatoleum evansii

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.B5 0.1
-
 3,4-dihydroxyphenylacetyl-CoA pH 8.1, 25°C, mutant enzyme D75A Aromatoleum evansii
3.1.2.B5 0.7
-
 3-hydroxyphenylacetyl-CoA pH 8.1, 25°C, mutant enzyme D16A Escherichia coli
3.1.2.B5 0.7
-
 4-hydroxyphenylacetyl-CoA pH 8.1, 25°C, mutant enzyme D16A Escherichia coli
3.1.2.B5 1
-
 4-hydroxyphenylacetyl-CoA pH 8.1, 25°C, mutant enzyme N46A Escherichia coli
3.1.2.B5 1
-
 3,4-dihydroxyphenylacetyl-CoA pH 8.1, 25°C, mutant enzyme N60A Aromatoleum evansii
3.1.2.B5 3
-
 3,4-dihydroxyphenylacetyl-CoA pH 8.1, 25°C, mutant enzyme D16A Escherichia coli
3.1.2.B5 3
-
 3,4-dihydroxyphenylacetyl-CoA pH 8.1, 25°C, mutant enzyme N46A Escherichia coli
3.1.2.B5 3
-
 3,4-dihydroxyphenylacetyl-CoA pH 8.1, 25°C, mutant enzyme N60D Aromatoleum evansii
3.1.2.B5 4
-
 3-hydroxyphenylacetyl-CoA pH 8.1, 25°C, mutant enzyme N46A Escherichia coli
3.1.2.B5 9
-
 4-hydroxyphenylacetyl-CoA pH 8.1, 25°C, mutant enzyme H52A Escherichia coli
3.1.2.B5 10
-
 phenylacetyl-CoA pH 8.1, 25°C, wild-type enzyme Aromatoleum evansii
3.1.2.B5 30
-
 3-hydroxyphenylacetyl-CoA pH 8.1, 25°C, mutant enzyme H52A Escherichia coli
3.1.2.B5 43
-
 phenylacetyl-CoA pH 8.1, 25°C, wild-type enzyme Escherichia coli
3.1.2.B5 45
-
 3,5-dihydroxyphenylacetyl-CoA pH 8.1, 25°C, wild-type enzyme Escherichia coli
3.1.2.B5 60
-
 3,4-dihydroxyphenylacetyl-CoA pH 8.1, 25°C, mutant enzyme H52A Escherichia coli
3.1.2.B5 80
-
 3,5-dihydroxyphenylacetyl-CoA pH 8.1, 25°C, wild-type enzyme Aromatoleum evansii
3.1.2.B5 100
-
 3-hydroxyphenylacetyl-CoA pH 8.1, 25°C, wild-type enzyme Aromatoleum evansii
3.1.2.B5 200
-
 3-hydroxyphenylacetyl-CoA pH 8.1, 25°C, mutant enzyme E14A Escherichia coli
3.1.2.B5 200
-
 4-hydroxyphenylacetyl-CoA pH 8.1, 25°C, mutant enzyme E14A Escherichia coli
3.1.2.B5 200
-
 3,4-dihydroxyphenylacetyl-CoA pH 8.1, 25°C, mutant enzyme E14A Escherichia coli
3.1.2.B5 200
-
 4-hydroxyphenylacetyl-CoA pH 8.1, 25°C, mutant enzyme N15A Escherichia coli
3.1.2.B5 200
-
 4-hydroxyphenylacetyl-CoA pH 8.1, 25°C, wild-type enzyme Aromatoleum evansii
3.1.2.B5 400
-
 3,4-dihydroxyphenylacetyl-CoA pH 8.1, 25°C, wild-type enzyme Aromatoleum evansii
3.1.2.B5 600
-
 3,4-dihydroxyphenylacetyl-CoA pH 8.1, 25°C, mutant enzyme N15A Escherichia coli
3.1.2.B5 900
-
 3-hydroxyphenylacetyl-CoA pH 8.1, 25°C, mutant enzyme N15A Escherichia coli
3.1.2.B5 2257
-
 4-hydroxyphenylacetyl-CoA pH 8.1, 25°C, wild-type enzyme Escherichia coli
3.1.2.B5 4095
-
 3-hydroxyphenylacetyl-CoA pH 8.1, 25°C, wild-type enzyme Escherichia coli
3.1.2.B5 6250
-
 3,4-dihydroxyphenylacetyl-CoA pH 8.1, 25°C, wild-type enzyme Escherichia coli