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Literature summary for 4.1.99.2 extracted from

  • Miao, L.; Li, Q.; Diao, A.; Zhang, X.; Ma, Y.
    Construction of a novel phenol synthetic pathway in Escherichia coli through 4-hydroxybenzoate decarboxylation (2015), Appl. Microbiol. Biotechnol., 99, 5163-5173 .
    View publication on PubMed
Search for more literature for 4.1.99.2

Protein Variants

Protein Variants Comment Organism
S51A site-directed mutagenesis, the mutation leads to a decrease of the kcat/Km parameter for reactions with L-tyrosine and 3-fluoro-L-tyrosine by three orders of magnitude, compared to the wild-type enzyme, phenotype, overview. Influence of replacement of Ser51 by Ala on the kinetic parameters of TPL reactions with inhibitory L-phenylalanine and L-methionine, kinetics and structures, overview Citrobacter freundii

Inhibitors

Inhibitors Comment Organism Structure
L-methionine inhibition of alpha,beta-elimination reaction Citrobacter freundii
L-phenylalanine inhibition of alpha,beta-elimination reaction Citrobacter freundii
additional information The mutant S51A also shows intermediate formation with L-Met and L-Phe. Influence of replacement of Ser51 by Ala on the kinetic parameters of TPL reactions with L-phenylalanine and L-methionine, kinetics and structures, overview Citrobacter freundii

KM Value [mM]

KM Value [mM] KM Value Maximum [mM] Substrate Comment Organism Structure
additional information
-
 additional information steady-state kinetics Citrobacter freundii
0.1
-
 3-fluoro-L-tyrosine recombinant wild-type enzyme, pH 8.0, 30°C Citrobacter freundii
0.12
-
 S-Benzyl-L-cysteine recombinant wild-type enzyme, pH 8.0, 30°C Citrobacter freundii
0.2
-
 L-tyrosine recombinant wild-type enzyme, pH 8.0, 30°C Citrobacter freundii
0.21
-
 S-(2-nitrophenyl)-L-cysteine recombinant wild-type enzyme, pH 8.0, 30°C Citrobacter freundii
0.8
-
 beta-chloro-L-alanine recombinant mutant S51A, pH 8.0, 30°C Citrobacter freundii
1.3
-
 L-tyrosine recombinant mutant S51A, pH 8.0, 30°C Citrobacter freundii
1.3
-
 3-fluoro-L-tyrosine recombinant mutant S51A, pH 8.0, 30°C Citrobacter freundii
1.57
-
 S-ethyl-L-cysteine recombinant wild-type enzyme, pH 8.0, 30°C Citrobacter freundii
2.12
-
 beta-chloro-L-alanine recombinant wild-type enzyme, pH 8.0, 30°C Citrobacter freundii
2.2
-
 S-(2-nitrophenyl)-L-cysteine recombinant mutant S51A, pH 8.0, 30°C Citrobacter freundii
2.32
-
 S-methyl-L-cysteine recombinant wild-type enzyme, pH 8.0, 30°C Citrobacter freundii
4.1
-
 S-Benzyl-L-cysteine recombinant mutant S51A, pH 8.0, 30°C Citrobacter freundii
5.4
-
 S-ethyl-L-cysteine recombinant mutant S51A, pH 8.0, 30°C Citrobacter freundii
10.5
-
 S-methyl-L-cysteine recombinant mutant S51A, pH 8.0, 30°C Citrobacter freundii

Natural Substrates/ Products (Substrates)

Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
L-tyrosine + H2O Citrobacter freundii
-
 phenol + pyruvate + NH3
-
 r

Organism

Organism UniProt Comment Textmining
Citrobacter freundii P31013
-
-

Reaction

Reaction Comment Organism Reaction ID
L-tyrosine + H2O = phenol + pyruvate + NH3 mechanism of alpha,beta-elimination of L-tyrosine catalyzed by enzyme TPL Citrobacter freundii
a

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
3-fluoro-L-tyrosine + H2O
-
 Citrobacter freundii 3-fluorophenol + pyruvate + NH3
-
 r
beta-chloro-L-alanine + H2O
-
 Citrobacter freundii Cl- + pyruvate + NH3
-
 r
L-tyrosine + H2O
-
 Citrobacter freundii phenol + pyruvate + NH3
-
 r
additional information fragment of active site structure of the quinonoid complex of wild-type enzyme TPL with L-alanine, overview Citrobacter freundii ?
-
 ?
S-(2-nitrophenyl)-L-cysteine + H2O
-
 Citrobacter freundii 2-nitrobenzenethiolate + pyruvate + NH3
-
 r
S-benzyl-L-cysteine + H2O
-
 Citrobacter freundii thiophenol + pyruvate + NH3
-
 r
S-ethyl-L-cysteine + H2O
-
 Citrobacter freundii ethanethiol + pyruvate + NH3
-
 r
S-methyl-L-cysteine + H2O
-
 Citrobacter freundii methanethiol + pyruvate + NH3
-
 r

Synonyms

Synonyms Comment Organism
TPL
-
 Citrobacter freundii

Temperature Optimum [°C]

Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
30
-
 assay at Citrobacter freundii

Turnover Number [1/s]

Turnover Number Minimum [1/s] Turnover Number Maximum [1/s] Substrate Comment Organism Structure
0.012
-
 3-fluoro-L-tyrosine recombinant mutant S51A, pH 8.0, 30°C Citrobacter freundii
0.015
-
 S-Benzyl-L-cysteine recombinant mutant S51A, pH 8.0, 30°C Citrobacter freundii
0.03
-
 L-tyrosine recombinant mutant S51A, pH 8.0, 30°C Citrobacter freundii
0.044
-
 S-methyl-L-cysteine recombinant mutant S51A, pH 8.0, 30°C Citrobacter freundii
0.083
-
 S-ethyl-L-cysteine recombinant mutant S51A, pH 8.0, 30°C Citrobacter freundii
0.15
-
 beta-chloro-L-alanine recombinant mutant S51A, pH 8.0, 30°C Citrobacter freundii
0.63
-
 S-Benzyl-L-cysteine recombinant wild-type enzyme, pH 8.0, 30°C Citrobacter freundii
1.13
-
 S-methyl-L-cysteine recombinant wild-type enzyme, pH 8.0, 30°C Citrobacter freundii
1.4
-
 3-fluoro-L-tyrosine recombinant wild-type enzyme, pH 8.0, 30°C Citrobacter freundii
3.5
-
 L-tyrosine recombinant wild-type enzyme, pH 8.0, 30°C Citrobacter freundii
5.4
-
 S-ethyl-L-cysteine recombinant wild-type enzyme, pH 8.0, 30°C Citrobacter freundii
6
-
 beta-chloro-L-alanine recombinant wild-type enzyme, pH 8.0, 30°C Citrobacter freundii
8.7
-
 S-(2-nitrophenyl)-L-cysteine recombinant mutant S51A, pH 8.0, 30°C Citrobacter freundii
9.65
-
 S-(2-nitrophenyl)-L-cysteine recombinant wild-type enzyme, pH 8.0, 30°C Citrobacter freundii

pH Optimum

pH Optimum Minimum pH Optimum Maximum Comment Organism
8
-
 assay at Citrobacter freundii

Cofactor

Cofactor Comment Organism Structure
pyridoxal 5'-phosphate dependent on Citrobacter freundii

Ki Value [mM]

Ki Value [mM] Ki Value maximum [mM] Inhibitor Comment Organism Structure
additional information
-
 additional information rapid scanning stopped-flow kinetic experiments, kinetics Citrobacter freundii

General Information

General Information Comment Organism
additional information the Ser51 residue interacts with the side chain amino group of Lys257 at the stage of C-alpha-proton abstraction. This interaction ensures the correct orientation of the side chain of Lys257 accepting the C-alpha-proton of the external aldimine and stabilizes its ammonium form. Ser51 takes part in formation of a chain of hydrogen bonds which is necessary to perform the transfer of the Calpha-proton to the C-4'-position of the leaving phenol group in the reaction with the natural substrate. Ser51 is necessary for efficient C-alpha-proton abstraction and its following transfer to the 4'-position of the leaving phenol group in the alpha,beta-elimination reaction of L-tyrosine Citrobacter freundii

kcat/KM [mM/s]

kcat/KM Value [1/mMs-1] kcat/KM Value Maximum [1/mMs-1] Substrate Comment Organism Structure
0.0037
-
 S-Benzyl-L-cysteine recombinant mutant S51A, pH 8.0, 30°C Citrobacter freundii
0.0042
-
 S-methyl-L-cysteine recombinant mutant S51A, pH 8.0, 30°C Citrobacter freundii
0.0092
-
 3-fluoro-L-tyrosine recombinant mutant S51A, pH 8.0, 30°C Citrobacter freundii
0.015
-
 S-ethyl-L-cysteine recombinant mutant S51A, pH 8.0, 30°C Citrobacter freundii
0.022
-
 L-tyrosine recombinant mutant S51A, pH 8.0, 30°C Citrobacter freundii
0.19
-
 beta-chloro-L-alanine recombinant mutant S51A, pH 8.0, 30°C Citrobacter freundii
0.49
-
 S-methyl-L-cysteine recombinant wild-type enzyme, pH 8.0, 30°C Citrobacter freundii
2.84
-
 beta-chloro-L-alanine recombinant wild-type enzyme, pH 8.0, 30°C Citrobacter freundii
3.43
-
 S-ethyl-L-cysteine recombinant wild-type enzyme, pH 8.0, 30°C Citrobacter freundii
3.9
-
 S-(2-nitrophenyl)-L-cysteine recombinant mutant S51A, pH 8.0, 30°C Citrobacter freundii
5.26
-
 S-Benzyl-L-cysteine recombinant wild-type enzyme, pH 8.0, 30°C Citrobacter freundii
14
-
 3-fluoro-L-tyrosine recombinant wild-type enzyme, pH 8.0, 30°C Citrobacter freundii
17.5
-
 L-tyrosine recombinant wild-type enzyme, pH 8.0, 30°C Citrobacter freundii
46
-
 S-(2-nitrophenyl)-L-cysteine recombinant wild-type enzyme, pH 8.0, 30°C Citrobacter freundii