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Literature summary 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

Activating Compound

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

Cloned(Commentary)

EC Number Cloned (Comment) Organism
3.1.2.12 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

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

Inhibitors

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

KM Value [mM]

EC Number KM Value [mM] KM Value Maximum [mM] Substrate Comment Organism Structure
3.1.2.12 0.29
-
 4-nitrophenyl acetate pH 8.0, 37°C, recombinant FrmB Escherichia coli
3.1.2.12 0.41
-
 S-formylglutathione pH 8.0, 37°C, recombinant FrmB Escherichia coli
3.1.2.12 0.43
-
 S-formylglutathione pH 8.0, 37°C, recombinant wild-type YeiG Escherichia coli
3.1.2.12 0.45
-
 4-nitrophenyl acetate pH 8.0, 37°C, recombinant wild-type YeiG Escherichia coli
3.1.2.12 0.48
-
 4-nitrophenyl propionate pH 8.0, 37°C, recombinant wild-type YeiG Escherichia coli
3.1.2.12 0.54
-
 Alpha-naphthyl acetate pH 8.0, 37°C, recombinant YeiG mutant D255A Escherichia coli
3.1.2.12 0.58
-
 S-Lactoylglutathione pH 8.0, 37°C, recombinant wild-type YeiG Escherichia coli
3.1.2.12 0.6
-
 S-Lactoylglutathione pH 8.0, 37°C, recombinant FrmB Escherichia coli
3.1.2.12 0.7
-
 4-nitrophenyl butyrate pH 8.0, 37°C, recombinant wild-type YeiG Escherichia coli
3.1.2.12 0.8
-
 Alpha-naphthyl acetate pH 8.0, 37°C, recombinant YeiG mutant D80A Escherichia coli
3.1.2.12 0.83
-
 4-nitrophenyl propionate pH 8.0, 37°C, recombinant FrmB Escherichia coli
3.1.2.12 0.95
-
 4-nitrophenyl caproate pH 8.0, 37°C, recombinant wild-type YeiG Escherichia coli
3.1.2.12 1.01
-
 Alpha-naphthyl acetate pH 8.0, 37°C, recombinant YeiG mutant D199A Escherichia coli
3.1.2.12 1.03
-
 Alpha-naphthyl acetate pH 8.0, 37°C, recombinant wild-type YeiG Escherichia coli
3.1.2.12 1.06
-
 Alpha-naphthyl acetate pH 8.0, 37°C, recombinant YeiG mutant C26A Escherichia coli
3.1.2.12 1.28
-
 Alpha-naphthyl acetate pH 8.0, 37°C, recombinant YeiG mutant C54A Escherichia coli
3.1.2.12 1.3
-
 Alpha-naphthyl acetate pH 8.0, 37°C, recombinant YeiG mutant D218A Escherichia coli

Natural Substrates/ Products (Substrates)

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

Organism

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

Purification (Commentary)

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

Reaction

EC Number Reaction Comment Organism Reaction ID
3.1.2.12 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

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

Specific Activity [micromol/min/mg]

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

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
3.1.2.12 2-naphthyl acetate + H2O artificial substrate of YeiG Escherichia coli 2-naphthol + acetate
-
 ?
3.1.2.12 2-naphthyl acetate + H2O artificial substrate of YeiG Escherichia coli BW25113 2-naphthol + acetate
-
 ?
3.1.2.12 4-nitrophenyl acetate + H2O artificial substrate of FrmB and YeiG Escherichia coli 4-nitrophenol + acetate
-
 ?
3.1.2.12 4-nitrophenyl acetate + H2O artificial substrate of FrmB and YeiG Escherichia coli BW25113 4-nitrophenol + acetate
-
 ?
3.1.2.12 4-nitrophenyl butyrate + H2O artificial substrate of YeiG Escherichia coli 4-nitrophenol + butyrate
-
 ?
3.1.2.12 4-nitrophenyl caproate + H2O artificial substrate of YeiG Escherichia coli 4-nitrophenol + caproate
-
 ?
3.1.2.12 4-nitrophenyl propionate + H2O artificial substrate of FrmB and YeiG Escherichia coli 4-nitrophenol + propionate
-
 ?
3.1.2.12 alpha-naphthyl acetate + H2O
-
 Escherichia coli alpha-naphthol + acetate
-
 ?
3.1.2.12 alpha-naphthyl acetate + H2O
-
 Escherichia coli BW25113 alpha-naphthol + acetate
-
 ?
3.1.2.12 additional information no activity by FrmB and YeiG with S-(1,2-dicarboxyethyl)glutathione, S-hexylglutathione, and S-(4-nitrobenzyl)glutathione Escherichia coli ?
-
 ?
3.1.2.12 additional information no activity by FrmB and YeiG with S-(1,2-dicarboxyethyl)glutathione, S-hexylglutathione, and S-(4-nitrobenzyl)glutathione Escherichia coli BW25113 ?
-
 ?
3.1.2.12 S-formylglutathione + H2O the substrate is an intermediate in the glutathione-dependent formaldehyde detoxification pathway Escherichia coli glutathione + formate
-
 ?
3.1.2.12 S-formylglutathione + H2O best substrate of FrmB and YeiG Escherichia coli glutathione + formate
-
 ?
3.1.2.12 S-formylglutathione + H2O the substrate is an intermediate in the glutathione-dependent formaldehyde detoxification pathway Escherichia coli BW25113 glutathione + formate
-
 ?
3.1.2.12 S-lactoylglutathione + H2O substrate of FrmB and YeiG Escherichia coli glutathione + lactate
-
 ?

Subunits

EC Number Subunits Comment Organism
3.1.2.12 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

EC Number Synonyms Comment Organism
3.1.2.12 FrmB
-
 Escherichia coli
3.1.2.12 YeiG
-
 Escherichia coli

Temperature Optimum [°C]

EC Number Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
3.1.2.12 37
-
 assay at Escherichia coli

Turnover Number [1/s]

EC Number Turnover Number Minimum [1/s] Turnover Number Maximum [1/s] Substrate Comment Organism Structure
3.1.2.12 0.05
-
 S-Lactoylglutathione pH 8.0, 37°C, recombinant FrmB Escherichia coli
3.1.2.12 0.14
-
 4-nitrophenyl propionate pH 8.0, 37°C, recombinant FrmB Escherichia coli
3.1.2.12 0.26
-
 4-nitrophenyl acetate pH 8.0, 37°C, recombinant wild-type YeiG Escherichia coli
3.1.2.12 0.3
-
 4-nitrophenyl acetate pH 8.0, 37°C, recombinant FrmB Escherichia coli
3.1.2.12 0.36
-
 4-nitrophenyl butyrate pH 8.0, 37°C, recombinant wild-type YeiG Escherichia coli
3.1.2.12 0.37
-
 4-nitrophenyl propionate pH 8.0, 37°C, recombinant wild-type YeiG Escherichia coli
3.1.2.12 0.49
-
 4-nitrophenyl caproate pH 8.0, 37°C, recombinant wild-type YeiG Escherichia coli
3.1.2.12 1.02
-
 S-Lactoylglutathione pH 8.0, 37°C, recombinant wild-type YeiG Escherichia coli
3.1.2.12 2.17
-
 Alpha-naphthyl acetate pH 8.0, 37°C, recombinant YeiG mutant D80A Escherichia coli
3.1.2.12 2.23
-
 Alpha-naphthyl acetate pH 8.0, 37°C, recombinant YeiG mutant D255A Escherichia coli
3.1.2.12 2.96
-
 Alpha-naphthyl acetate pH 8.0, 37°C, recombinant YeiG mutant D199A Escherichia coli
3.1.2.12 3.13
-
 Alpha-naphthyl acetate pH 8.0, 37°C, recombinant YeiG mutant D218A Escherichia coli
3.1.2.12 3.3
-
 Alpha-naphthyl acetate pH 8.0, 37°C, recombinant wild-type YeiG Escherichia coli
3.1.2.12 3.81
-
 Alpha-naphthyl acetate pH 8.0, 37°C, recombinant YeiG mutant D218A Escherichia coli
3.1.2.12 5.09
-
 Alpha-naphthyl acetate pH 8.0, 37°C, recombinant wild-type YeiG Escherichia coli
3.1.2.12 5.1
-
 Alpha-naphthyl acetate pH 8.0, 37°C, recombinant YeiG mutant C54A Escherichia coli
3.1.2.12 5.12
-
 Alpha-naphthyl acetate pH 8.0, 37°C, recombinant YeiG mutant C26A Escherichia coli
3.1.2.12 6.51
-
 S-formylglutathione pH 8.0, 37°C, recombinant wild-type YeiG Escherichia coli
3.1.2.12 28.5
-
 S-formylglutathione pH 8.0, 37°C, recombinant FrmB Escherichia coli

pH Optimum

EC Number pH Optimum Minimum pH Optimum Maximum Comment Organism
3.1.2.12 8
-
 assay at Escherichia coli