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Literature summary for 3.1.2.12 extracted from

  • Gonzalez, C.F.; Proudfoot, M.; Brown, G.; Korniyenko, Y.; Mori, H.; Savchenko, A.V.; Yakunin, A.F.
    Molecular basis of formaldehyde detoxification: Characterization of two s-formylglutathione hydrolases from Escherichia coli, FrmB and YeiG (2006), J. Biol. Chem., 282, 14514-14522.
    View publication on PubMed
Search for more literature for 3.1.2.12

Activating Compound

Activating Compound Comment Organism Structure
additional information FrmB is induced 45-75fold by formaldehyde, while YeiG is constitutively expressed Escherichia coli

Cloned(Commentary)

Cloned (Comment) Organism
genes frmB or yaiM, and yeiG, subcloning in strain DH5alpha, overexpression in strain BL21(DE3) of His-tagged wild-type and mutant enzymes Escherichia coli

Protein Variants

Protein Variants Comment Organism
C26A site-directed mutagenesis, the YeiG mutant shows wild-type activity Escherichia coli
C54A site-directed mutagenesis, the YeiG mutant shows wild-type activity Escherichia coli
D199A site-directed mutagenesis, the YeiG mutant shows reduced activity compared to the wild-type enzyme Escherichia coli
D218A site-directed mutagenesis, the YeiG mutant shows reduced activity compared to the wild-type enzyme Escherichia coli
D223A site-directed mutagenesis, the YeiG mutant shows no esterase activity Escherichia coli
D255A site-directed mutagenesis, the YeiG mutant shows 2fold reduced activity compared to the wild-type enzyme Escherichia coli
D80A site-directed mutagenesis, the YeiG mutant shows reduced activity compared to the wild-type enzyme Escherichia coli
additional information construction of FrmB and YeiG deletion mutants Escherichia coli
S154A site-directed mutagenesis, the YeiG mutant shows no esterase activity Escherichia coli

Inhibitors

Inhibitors Comment Organism Structure
NEM inhibition of wild-type YeiG and YeiG mutant C26A, no inhibition of YeiG mutant C54A Escherichia coli
PMSF inhibition of wild-type YeiG and YeiG mutants C54A and C26A Escherichia coli

KM Value [mM]

KM Value [mM] KM Value Maximum [mM] Substrate Comment Organism Structure
0.29
-
 4-nitrophenyl acetate pH 8.0, 37°C, recombinant FrmB Escherichia coli
0.41
-
 S-formylglutathione pH 8.0, 37°C, recombinant FrmB Escherichia coli
0.43
-
 S-formylglutathione pH 8.0, 37°C, recombinant wild-type YeiG Escherichia coli
0.45
-
 4-nitrophenyl acetate pH 8.0, 37°C, recombinant wild-type YeiG Escherichia coli
0.48
-
 4-nitrophenyl propionate pH 8.0, 37°C, recombinant wild-type YeiG Escherichia coli
0.54
-
 Alpha-naphthyl acetate pH 8.0, 37°C, recombinant YeiG mutant D255A Escherichia coli
0.58
-
 S-Lactoylglutathione pH 8.0, 37°C, recombinant wild-type YeiG Escherichia coli
0.6
-
 S-Lactoylglutathione pH 8.0, 37°C, recombinant FrmB Escherichia coli
0.7
-
 4-nitrophenyl butyrate pH 8.0, 37°C, recombinant wild-type YeiG Escherichia coli
0.8
-
 Alpha-naphthyl acetate pH 8.0, 37°C, recombinant YeiG mutant D80A Escherichia coli
0.83
-
 4-nitrophenyl propionate pH 8.0, 37°C, recombinant FrmB Escherichia coli
0.95
-
 4-nitrophenyl caproate pH 8.0, 37°C, recombinant wild-type YeiG Escherichia coli
1.01
-
 Alpha-naphthyl acetate pH 8.0, 37°C, recombinant YeiG mutant D199A Escherichia coli
1.03
-
 Alpha-naphthyl acetate pH 8.0, 37°C, recombinant wild-type YeiG Escherichia coli
1.06
-
 Alpha-naphthyl acetate pH 8.0, 37°C, recombinant YeiG mutant C26A Escherichia coli
1.28
-
 Alpha-naphthyl acetate pH 8.0, 37°C, recombinant YeiG mutant C54A Escherichia coli
1.3
-
 Alpha-naphthyl acetate pH 8.0, 37°C, recombinant YeiG mutant D218A Escherichia coli

Natural Substrates/ Products (Substrates)

Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
S-formylglutathione + H2O Escherichia coli the substrate is an intermediate in the glutathione-dependent formaldehyde detoxification pathway glutathione + formate
-
 ?
S-formylglutathione + H2O Escherichia coli BW25113 the substrate is an intermediate in the glutathione-dependent formaldehyde detoxification pathway glutathione + formate
-
 ?

Organism

Organism UniProt Comment Textmining
Escherichia coli
-
 2 enzymes FrmB and YeiG, encoded by genes frmB or yaiM, and yeiG
-
Escherichia coli BW25113
-
 2 enzymes FrmB and YeiG, encoded by genes frmB or yaiM, and yeiG
-

Purification (Commentary)

Purification (Comment) Organism
recombinant His-tagged wild-type and mutant enzymes from strain BL21(DE3) by nickel affinity chromatography Escherichia coli

Reaction

Reaction Comment Organism Reaction ID
S-formylglutathione + H2O = glutathione + formate Ser145, Asp233, and His256 are essential for catalysis, representing a serine hydrolase catalytic triad, Cys26 and Cys54 are not involved in catalysis, mechanism Escherichia coli
a

Source Tissue

Source Tissue Comment Organism Textmining
additional information expression levels of wild-type and mutant enzymes, induced or uninduced, overview Escherichia coli
-

Specific Activity [micromol/min/mg]

Specific Activity Minimum [µmol/min/mg] Specific Activity Maximum [µmol/min/mg] Comment Organism
additional information
-
 substrate specificity Escherichia coli

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
2-naphthyl acetate + H2O artificial substrate of YeiG Escherichia coli 2-naphthol + acetate
-
 ?
2-naphthyl acetate + H2O artificial substrate of YeiG Escherichia coli BW25113 2-naphthol + acetate
-
 ?
4-nitrophenyl acetate + H2O artificial substrate of FrmB and YeiG Escherichia coli 4-nitrophenol + acetate
-
 ?
4-nitrophenyl acetate + H2O artificial substrate of FrmB and YeiG Escherichia coli BW25113 4-nitrophenol + acetate
-
 ?
4-nitrophenyl butyrate + H2O artificial substrate of YeiG Escherichia coli 4-nitrophenol + butyrate
-
 ?
4-nitrophenyl caproate + H2O artificial substrate of YeiG Escherichia coli 4-nitrophenol + caproate
-
 ?
4-nitrophenyl propionate + H2O artificial substrate of FrmB and YeiG Escherichia coli 4-nitrophenol + propionate
-
 ?
alpha-naphthyl acetate + H2O
-
 Escherichia coli alpha-naphthol + acetate
-
 ?
alpha-naphthyl acetate + H2O
-
 Escherichia coli BW25113 alpha-naphthol + acetate
-
 ?
additional information no activity by FrmB and YeiG with S-(1,2-dicarboxyethyl)glutathione, S-hexylglutathione, and S-(4-nitrobenzyl)glutathione Escherichia coli ?
-
 ?
additional information no activity by FrmB and YeiG with S-(1,2-dicarboxyethyl)glutathione, S-hexylglutathione, and S-(4-nitrobenzyl)glutathione Escherichia coli BW25113 ?
-
 ?
S-formylglutathione + H2O the substrate is an intermediate in the glutathione-dependent formaldehyde detoxification pathway Escherichia coli glutathione + formate
-
 ?
S-formylglutathione + H2O best substrate of FrmB and YeiG Escherichia coli glutathione + formate
-
 ?
S-formylglutathione + H2O the substrate is an intermediate in the glutathione-dependent formaldehyde detoxification pathway Escherichia coli BW25113 glutathione + formate
-
 ?
S-lactoylglutathione + H2O substrate of FrmB and YeiG Escherichia coli glutathione + lactate
-
 ?

Subunits

Subunits Comment Organism
More structure analysis in comparison to the Saccharomyces cerevisiae crystal structure, PDB code 1pv1, the enzyme shows a canonical alpha/beta-hydrolase fold Escherichia coli

Synonyms

Synonyms Comment Organism
FrmB
-
 Escherichia coli
YeiG
-
 Escherichia coli

Temperature Optimum [°C]

Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
37
-
 assay at Escherichia coli

Turnover Number [1/s]

Turnover Number Minimum [1/s] Turnover Number Maximum [1/s] Substrate Comment Organism Structure
0.05
-
 S-Lactoylglutathione pH 8.0, 37°C, recombinant FrmB Escherichia coli
0.14
-
 4-nitrophenyl propionate pH 8.0, 37°C, recombinant FrmB Escherichia coli
0.26
-
 4-nitrophenyl acetate pH 8.0, 37°C, recombinant wild-type YeiG Escherichia coli
0.3
-
 4-nitrophenyl acetate pH 8.0, 37°C, recombinant FrmB Escherichia coli
0.36
-
 4-nitrophenyl butyrate pH 8.0, 37°C, recombinant wild-type YeiG Escherichia coli
0.37
-
 4-nitrophenyl propionate pH 8.0, 37°C, recombinant wild-type YeiG Escherichia coli
0.49
-
 4-nitrophenyl caproate pH 8.0, 37°C, recombinant wild-type YeiG Escherichia coli
1.02
-
 S-Lactoylglutathione pH 8.0, 37°C, recombinant wild-type YeiG Escherichia coli
2.17
-
 Alpha-naphthyl acetate pH 8.0, 37°C, recombinant YeiG mutant D80A Escherichia coli
2.23
-
 Alpha-naphthyl acetate pH 8.0, 37°C, recombinant YeiG mutant D255A Escherichia coli
2.96
-
 Alpha-naphthyl acetate pH 8.0, 37°C, recombinant YeiG mutant D199A Escherichia coli
3.13
-
 Alpha-naphthyl acetate pH 8.0, 37°C, recombinant YeiG mutant D218A Escherichia coli
3.3
-
 Alpha-naphthyl acetate pH 8.0, 37°C, recombinant wild-type YeiG Escherichia coli
3.81
-
 Alpha-naphthyl acetate pH 8.0, 37°C, recombinant YeiG mutant D218A Escherichia coli
5.09
-
 Alpha-naphthyl acetate pH 8.0, 37°C, recombinant wild-type YeiG Escherichia coli
5.1
-
 Alpha-naphthyl acetate pH 8.0, 37°C, recombinant YeiG mutant C54A Escherichia coli
5.12
-
 Alpha-naphthyl acetate pH 8.0, 37°C, recombinant YeiG mutant C26A Escherichia coli
6.51
-
 S-formylglutathione pH 8.0, 37°C, recombinant wild-type YeiG Escherichia coli
28.5
-
 S-formylglutathione pH 8.0, 37°C, recombinant FrmB Escherichia coli

pH Optimum

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