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Literature summary for 4.2.1.113 extracted from

  • Zhu, W.W.; Wang, C.; Jipp, J.; Ferguson, L.; Lucas, S.N.; Hicks, M.A.; Glasner, M.E.
    Residues required for activity in Escherichia coli o-succinylbenzoate synthase (OSBS) are not conserved in all OSBS enzymes (2012), Biochemistry, 51, 6171-6181.
    View publication on PubMed
Search for more literature for 4.2.1.113

Cloned(Commentary)

Cloned (Comment) Organism
gene menC, phylogenetic analysis, expression of wild-type enzme in Escherichia coli strain BL21(DE3), expression of mutant enzymes in Escherichia coli strain BW25113 (menC::kan), which is converted into a DE3 strain to express T7 RNA polymerase Escherichia coli

Protein Variants

Protein Variants Comment Organism
F51A site-directed mutagenesis, the mutant shows reduced activity compared to the wild-type enzyme Escherichia coli
F51Y site-directed mutagenesis, the mutant shows reduced activity compared to the wild-type enzyme Escherichia coli
G16P/V17F/V18R/L19T/R20S/D21F/R22G/R23T/L24QL48A site-directed mutagenesis, the mutant shows reduced activity compared to the wild-type enzyme Escherichia coli
G288A site-directed mutagenesis, the mutant shows highly reduced activity compared to the wild-type enzyme, G288A introduces a steric clash with the substrate, reducing kcat/KM over 500fold Escherichia coli
I265A site-directed mutagenesis, the mutant shows reduced activity compared to the wild-type enzyme Escherichia coli
L109A site-directed mutagenesis, the mutant shows reduced activity compared to the wild-type enzyme Escherichia coli
L19A site-directed mutagenesis, the mutant shows reduced activity compared to the wild-type enzyme Escherichia coli
L48A/F51A site-directed mutagenesis, the mutant shows reduced activity compared to the wild-type enzyme Escherichia coli
L48M site-directed mutagenesis, the mutant shows reduced activity compared to the wild-type enzyme Escherichia coli
L48M/F51Y site-directed mutagenesis, the mutant shows reduced activity compared to the wild-type enzyme Escherichia coli
additional information 20s loop is truncated by deleting residues V17, V18, L19, R20, D21, R22, R23, and L24 resulting in a mutant with highly reduced activity compared to the wild-type enzyme Escherichia coli
R159M site-directed mutagenesis, the mutant shows highly reduced activity compared to the wild-type enzyme Escherichia coli
S262A/S263A/S264A/I265A site-directed mutagenesis, the mutant shows reduced activity compared to the wild-type enzyme Escherichia coli
S262G site-directed mutagenesis, the mutant shows reduced activity compared to the wild-type enzyme Escherichia coli
S262T site-directed mutagenesis, the mutant shows reduced activity compared to the wild-type enzyme Escherichia coli
S263G site-directed mutagenesis, the mutant shows reduced activity compared to the wild-type enzyme Escherichia coli
S264A site-directed mutagenesis, the mutant shows reduced activity compared to the wild-type enzyme Escherichia coli
T291S site-directed mutagenesis, the mutant shows reduced activity compared to the wild-type enzyme Escherichia coli
V233N site-directed mutagenesis, the mutant shows reduced activity compared to the wild-type enzyme Escherichia coli

KM Value [mM]

KM Value [mM] KM Value Maximum [mM] Substrate Comment Organism Structure
0.0096
-
 (1R,6R)-6-hydroxy-2-succinylcyclohexa-2,4-diene-1-carboxylate pH 8.0, 25°C, recombinant mutant G16P/V17F/V18R/L19T/R20S/D21F/R22G/R23T/L24QL48A Escherichia coli
0.01
-
 (1R,6R)-6-hydroxy-2-succinylcyclohexa-2,4-diene-1-carboxylate pH 8.0, 25°C, recombinant mutant I265A Escherichia coli
0.012
-
 (1R,6R)-6-hydroxy-2-succinylcyclohexa-2,4-diene-1-carboxylate pH 8.0, 25°C, recombinant wild-type enzyme Escherichia coli
0.013
-
 (1R,6R)-6-hydroxy-2-succinylcyclohexa-2,4-diene-1-carboxylate pH 8.0, 25°C, recombinant mutant L19A Escherichia coli
0.021
-
 (1R,6R)-6-hydroxy-2-succinylcyclohexa-2,4-diene-1-carboxylate pH 8.0, 25°C, recombinant mutant S262G Escherichia coli
0.029
-
 (1R,6R)-6-hydroxy-2-succinylcyclohexa-2,4-diene-1-carboxylate pH 8.0, 25°C, recombinant mutant S264A Escherichia coli
0.036
-
 (1R,6R)-6-hydroxy-2-succinylcyclohexa-2,4-diene-1-carboxylate pH 8.0, 25°C, recombinant mutant L109A Escherichia coli
0.051
-
 (1R,6R)-6-hydroxy-2-succinylcyclohexa-2,4-diene-1-carboxylate pH 8.0, 25°C, recombinant mutant F51Y Escherichia coli
0.051
-
 (1R,6R)-6-hydroxy-2-succinylcyclohexa-2,4-diene-1-carboxylate pH 8.0, 25°C, recombinant mutant S262A/S263A/S264A/I265A Escherichia coli
0.052
-
 (1R,6R)-6-hydroxy-2-succinylcyclohexa-2,4-diene-1-carboxylate pH 8.0, 25°C, recombinant mutant L48M Escherichia coli
0.073
-
 (1R,6R)-6-hydroxy-2-succinylcyclohexa-2,4-diene-1-carboxylate pH 8.0, 25°C, recombinant mutant L48M/F51Y Escherichia coli
0.08
-
 (1R,6R)-6-hydroxy-2-succinylcyclohexa-2,4-diene-1-carboxylate pH 8.0, 25°C, recombinant mutant R159M Escherichia coli
0.089
-
 (1R,6R)-6-hydroxy-2-succinylcyclohexa-2,4-diene-1-carboxylate pH 8.0, 25°C, recombinant mutant L48A/F51A Escherichia coli
0.099
-
 (1R,6R)-6-hydroxy-2-succinylcyclohexa-2,4-diene-1-carboxylate pH 8.0, 25°C, recombinant mutant V233N Escherichia coli
0.111
-
 (1R,6R)-6-hydroxy-2-succinylcyclohexa-2,4-diene-1-carboxylate pH 8.0, 25°C, recombinant mutant L48A Escherichia coli
0.122
-
 (1R,6R)-6-hydroxy-2-succinylcyclohexa-2,4-diene-1-carboxylate pH 8.0, 25°C, recombinant mutant F51A Escherichia coli
0.158
-
 (1R,6R)-6-hydroxy-2-succinylcyclohexa-2,4-diene-1-carboxylate pH 8.0, 25°C, recombinant mutant S263G Escherichia coli
0.206
-
 (1R,6R)-6-hydroxy-2-succinylcyclohexa-2,4-diene-1-carboxylate pH 8.0, 25°C, recombinant mutant T291S Escherichia coli
0.343
-
 (1R,6R)-6-hydroxy-2-succinylcyclohexa-2,4-diene-1-carboxylate pH 8.0, 25°C, recombinant mutant S262T Escherichia coli

Natural Substrates/ Products (Substrates)

Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
(1R,6R)-6-hydroxy-2-succinylcyclohexa-2,4-diene-1-carboxylate Escherichia coli
-
 2-succinylbenzoate + H2O
-
 ?

Organism

Organism UniProt Comment Textmining
Escherichia coli
-
 gene menC
-

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
(1R,6R)-6-hydroxy-2-succinylcyclohexa-2,4-diene-1-carboxylate
-
 Escherichia coli 2-succinylbenzoate + H2O
-
 ?

Synonyms

Synonyms Comment Organism
OSBS
-
 Escherichia coli

Temperature Optimum [°C]

Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
25
-
 assay at Escherichia coli

Turnover Number [1/s]

Turnover Number Minimum [1/s] Turnover Number Maximum [1/s] Substrate Comment Organism Structure
0.4
-
 (1R,6R)-6-hydroxy-2-succinylcyclohexa-2,4-diene-1-carboxylate pH 8.0, 25°C, recombinant mutant G16P/V17F/V18R/L19T/R20S/D21F/R22G/R23T/L24QL48A Escherichia coli
0.9
-
 (1R,6R)-6-hydroxy-2-succinylcyclohexa-2,4-diene-1-carboxylate pH 8.0, 25°C, recombinant mutant R159M Escherichia coli
2.7
-
 (1R,6R)-6-hydroxy-2-succinylcyclohexa-2,4-diene-1-carboxylate pH 8.0, 25°C, recombinant mutant S262A/S263A/S264A/I265A Escherichia coli
2.9
-
 (1R,6R)-6-hydroxy-2-succinylcyclohexa-2,4-diene-1-carboxylate pH 8.0, 25°C, recombinant mutant L109A Escherichia coli
3.9
-
 (1R,6R)-6-hydroxy-2-succinylcyclohexa-2,4-diene-1-carboxylate pH 8.0, 25°C, recombinant mutant L19A Escherichia coli
6
-
 (1R,6R)-6-hydroxy-2-succinylcyclohexa-2,4-diene-1-carboxylate pH 8.0, 25°C, recombinant mutant I265A Escherichia coli
10
-
 (1R,6R)-6-hydroxy-2-succinylcyclohexa-2,4-diene-1-carboxylate pH 8.0, 25°C, recombinant mutant S262G Escherichia coli
11
-
 (1R,6R)-6-hydroxy-2-succinylcyclohexa-2,4-diene-1-carboxylate pH 8.0, 25°C, recombinant mutant L48A/F51A Escherichia coli
12
-
 (1R,6R)-6-hydroxy-2-succinylcyclohexa-2,4-diene-1-carboxylate pH 8.0, 25°C, recombinant mutant S264A Escherichia coli
14
-
 (1R,6R)-6-hydroxy-2-succinylcyclohexa-2,4-diene-1-carboxylate pH 8.0, 25°C, recombinant mutant L48A Escherichia coli
18
-
 (1R,6R)-6-hydroxy-2-succinylcyclohexa-2,4-diene-1-carboxylate pH 8.0, 25°C, recombinant mutant F51Y Escherichia coli
24
-
 (1R,6R)-6-hydroxy-2-succinylcyclohexa-2,4-diene-1-carboxylate pH 8.0, 25°C, recombinant wild-type enzyme Escherichia coli
27
-
 (1R,6R)-6-hydroxy-2-succinylcyclohexa-2,4-diene-1-carboxylate pH 8.0, 25°C, recombinant mutant L48M/F51Y Escherichia coli
29
-
 (1R,6R)-6-hydroxy-2-succinylcyclohexa-2,4-diene-1-carboxylate pH 8.0, 25°C, recombinant mutant L48M Escherichia coli
49
-
 (1R,6R)-6-hydroxy-2-succinylcyclohexa-2,4-diene-1-carboxylate pH 8.0, 25°C, recombinant mutant F51A Escherichia coli
65
-
 (1R,6R)-6-hydroxy-2-succinylcyclohexa-2,4-diene-1-carboxylate pH 8.0, 25°C, recombinant mutant S262T Escherichia coli
67
-
 (1R,6R)-6-hydroxy-2-succinylcyclohexa-2,4-diene-1-carboxylate pH 8.0, 25°C, recombinant mutant T291S Escherichia coli
73
-
 (1R,6R)-6-hydroxy-2-succinylcyclohexa-2,4-diene-1-carboxylate pH 8.0, 25°C, recombinant mutant S263G Escherichia coli
94
-
 (1R,6R)-6-hydroxy-2-succinylcyclohexa-2,4-diene-1-carboxylate pH 8.0, 25°C, recombinant mutant V233N Escherichia coli

pH Optimum

pH Optimum Minimum pH Optimum Maximum Comment Organism
8
-
 assay at Escherichia coli

General Information

General Information Comment Organism
evolution the enzyme belongs to the o-succinylbenzoate synthase (OSBS) family, which is part of the enolase superfamily. Some enzymes in the OSBS family catalyze another reaction, N-succinylamino acid racemization (NSAR). NSARs cannot be segregated into a separate family because their sequences are highly similar to those of known OSBSs, and many of them have both OSBS and NSAR activities. Phylogenetic and sequence analysis Escherichia coli
metabolism the enzyme is required for menaquinone biosynthesis Escherichia coli

kcat/KM [mM/s]

kcat/KM Value [1/mMs-1] kcat/KM Value Maximum [1/mMs-1] Substrate Comment Organism Structure
3.8
-
 (1R,6R)-6-hydroxy-2-succinylcyclohexa-2,4-diene-1-carboxylate pH 8.0, 25°C, recombinant mutant G288A Escherichia coli
11
-
 (1R,6R)-6-hydroxy-2-succinylcyclohexa-2,4-diene-1-carboxylate pH 8.0, 25°C, recombinant mutant R159M Escherichia coli
43
-
 (1R,6R)-6-hydroxy-2-succinylcyclohexa-2,4-diene-1-carboxylate pH 8.0, 25°C, recombinant mutant G16P/V17F/V18R/L19T/R20S/D21F/R22G/R23T/L24QL48A Escherichia coli
53
-
 (1R,6R)-6-hydroxy-2-succinylcyclohexa-2,4-diene-1-carboxylate pH 8.0, 25°C, recombinant mutant S262A/S263A/S264A/I265A Escherichia coli
80
-
 (1R,6R)-6-hydroxy-2-succinylcyclohexa-2,4-diene-1-carboxylate pH 8.0, 25°C, recombinant mutant L109A Escherichia coli
130
-
 (1R,6R)-6-hydroxy-2-succinylcyclohexa-2,4-diene-1-carboxylate pH 8.0, 25°C, recombinant mutant L48A Escherichia coli
130
-
 (1R,6R)-6-hydroxy-2-succinylcyclohexa-2,4-diene-1-carboxylate pH 8.0, 25°C, recombinant mutant L48A/F51A Escherichia coli
190
-
 (1R,6R)-6-hydroxy-2-succinylcyclohexa-2,4-diene-1-carboxylate pH 8.0, 25°C, recombinant mutant S262T Escherichia coli
300
-
 (1R,6R)-6-hydroxy-2-succinylcyclohexa-2,4-diene-1-carboxylate pH 8.0, 25°C, recombinant mutant L19A Escherichia coli
330
-
 (1R,6R)-6-hydroxy-2-succinylcyclohexa-2,4-diene-1-carboxylate pH 8.0, 25°C, recombinant mutant T291S Escherichia coli
350
-
 (1R,6R)-6-hydroxy-2-succinylcyclohexa-2,4-diene-1-carboxylate pH 8.0, 25°C, recombinant mutant F51Y Escherichia coli
370
-
 (1R,6R)-6-hydroxy-2-succinylcyclohexa-2,4-diene-1-carboxylate pH 8.0, 25°C, recombinant mutant L48M/F51Y Escherichia coli
400
-
 (1R,6R)-6-hydroxy-2-succinylcyclohexa-2,4-diene-1-carboxylate pH 8.0, 25°C, recombinant mutant F51A Escherichia coli
410
-
 (1R,6R)-6-hydroxy-2-succinylcyclohexa-2,4-diene-1-carboxylate pH 8.0, 25°C, recombinant mutant S264A Escherichia coli
460
-
 (1R,6R)-6-hydroxy-2-succinylcyclohexa-2,4-diene-1-carboxylate pH 8.0, 25°C, recombinant mutant S263G Escherichia coli
480
-
 (1R,6R)-6-hydroxy-2-succinylcyclohexa-2,4-diene-1-carboxylate pH 8.0, 25°C, recombinant mutant S262G Escherichia coli
570
-
 (1R,6R)-6-hydroxy-2-succinylcyclohexa-2,4-diene-1-carboxylate pH 8.0, 25°C, recombinant mutant L48M Escherichia coli
580
-
 (1R,6R)-6-hydroxy-2-succinylcyclohexa-2,4-diene-1-carboxylate pH 8.0, 25°C, recombinant mutant I265A Escherichia coli
960
-
 (1R,6R)-6-hydroxy-2-succinylcyclohexa-2,4-diene-1-carboxylate pH 8.0, 25°C, recombinant mutant V233N Escherichia coli
2000
-
 (1R,6R)-6-hydroxy-2-succinylcyclohexa-2,4-diene-1-carboxylate pH 8.0, 25°C, recombinant wild-type enzyme Escherichia coli