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Literature summary extracted from

  • Miller, J.J.; Shah, I.T.; Hatten, J.; Barekatain, Y.; Mueller, E.A.; Moustafa, A.M.; Edwards, R.L.; Dowd, C.S.; Planet, P.; Muller, F.L.; Jez, J.; Odom John, A.R.
    Structure-guided microbial targeting of antistaphylococcal prodrugs (2021), eLife, 10, e66657 .
    View publication on PubMedView publication on EuropePMC

Crystallization (Commentary)

EC Number Crystallization (Comment) Organism
3.1.2.6 structure of SeMet-substituted protein, to 1.65 A resolution. Four monomers of GloB are observed in the asymmetric unit. GloB exhibits the classic alphabeta/betalpha-fold that defines the metallo-beta-lactamases Staphylococcus aureus
3.1.2.12 structure to 1.6 A resolution. A single dimer of FrmB is observed in the asymmetric unit. The overall fold of FrmB is characteristic of the alpha/beta-hydrolase fold Staphylococcus aureus

Organism

EC Number Organism UniProt Comment Textmining
3.1.2.6 Staphylococcus aureus A0A0D1GCF8
-
-
3.1.2.12 Staphylococcus aureus Q2FUY3
-
-
3.1.2.12 Staphylococcus aureus PS 47 Q2FUY3
-
-

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
3.1.2.6 (S)-D-lactoylglutathione + H2O
-
 Staphylococcus aureus D-lactate + glutathione
-
 ?
3.1.2.6 bis(pivaloyloxymethyl)(1-hydroxy-2-oxopiperidin-3-yl)phosphonate + H2O i.e. POM-HEX, substrate is a prodrug of the compound HEX, which inhibits the glycolytic enzyme enolase Staphylococcus aureus [[(hydroxymethoxy)(1-hydroxy-2-oxopiperidin-3-yl)phosphoryl]oxy]methyl 2,2-dimethylpropanoate + 2,2-dimethylpropanoate
-
 ?
3.1.2.6 fluorescein-3',6'-bis(oxy)methylene bis(2-methoxypropanoate) + H2O
-
 Staphylococcus aureus fluorescein-3'-oxymethyl 2-methoxypropanoate + 2-methoxypropanoate
-
 ?
3.1.2.6 fluorescein-3',6'-bis(oxy)methylene bis(ethoxyacetate) + H2O
-
 Staphylococcus aureus fluorescein-3'-yoxymethyl ethoxyacetate + ethoxyacetate
-
 ?
3.1.2.6 fluorescein-3',6'-bis(oxy)methylene bis(methoxyacetate) + H2O
-
 Staphylococcus aureus fluorescein-3'-oxymethyl methoxyacetate + methoxyacetate
-
 ?
3.1.2.6 fluorescein-3',6'-bis(oxy)methylene bis(propoxyacetate) + H2O
-
 Staphylococcus aureus fluorescein-3'-oxymethyl propoxyacetate + propoxyacetate
-
 ?
3.1.2.6 fluorescein-3',6'-bis(oxy)methylene bis[(ethylsulfanyl)acetate] + H2O
-
 Staphylococcus aureus fluorescein-3'-oxymethyl (ethylsulfanyl)acetate + (ethylsulfanyl)acetate
-
 ?
3.1.2.6 fluorescein-3',6'-bis(oxy)methylene bis[(methylsulfanyl)acetate] + H2O
-
 Staphylococcus aureus fluorescein-3'-oxymethyl (methylsulfanyl)acetate + (methylsulfanyl)acetate
-
 ?
3.1.2.6 fluorescein-3',6'-bis(oxy)methylene dibutanoate + H2O
-
 Staphylococcus aureus fluorescein-3'-oxymethyl butanoate + butanoate
-
 ?
3.1.2.6 fluorescein-3',6'-bis(oxy)methylene dihexanoate + H2O
-
 Staphylococcus aureus fluorescein-3'-oxymethyl hexanoate + hexanoate
-
 ?
3.1.2.6 fluorescein-3',6'-bis(oxy)methylene dipentanoate + H2O
-
 Staphylococcus aureus fluorescein-3'-oxymethyl pentanoate + pentanoate
-
 ?
3.1.2.6 additional information no substrates: 4-nitrophenyl acetate, 4-nitrophenyl butanoate, 4-nitrophenyl trimethylacetate Staphylococcus aureus ?
-
-
3.1.2.12 (S)-D-lactoylglutathione + H2O
-
 Staphylococcus aureus D-lactate + glutathione
-
 ?
3.1.2.12 (S)-D-lactoylglutathione + H2O
-
 Staphylococcus aureus PS 47 D-lactate + glutathione
-
 ?
3.1.2.12 bis(pivaloyloxymethyl)(1-hydroxy-2-oxopiperidin-3-yl)phosphonate + H2O i.e. POM-HEX, substrate is a prodrug of the compound HEX,which inhibits the glycolytic enzyme enolase Staphylococcus aureus [[(hydroxymethoxy)(1-hydroxy-2-oxopiperidin-3-yl)phosphoryl]oxy]methyl 2,2-dimethylpropanoate + 2,2-dimethylpropanoic acid
-
 ?
3.1.2.12 bis(pivaloyloxymethyl)(1-hydroxy-2-oxopiperidin-3-yl)phosphonate + H2O i.e. POM-HEX, substrate is a prodrug of the compound HEX,which inhibits the glycolytic enzyme enolase Staphylococcus aureus PS 47 [[(hydroxymethoxy)(1-hydroxy-2-oxopiperidin-3-yl)phosphoryl]oxy]methyl 2,2-dimethylpropanoate + 2,2-dimethylpropanoic acid
-
 ?
3.1.2.12 fluorescein-3',6'-bis(oxy)methylene bis(2-methoxypropanoate) + H2O
-
 Staphylococcus aureus fluorescein-3'-oxymethyl 2-methoxypropanoate + 2-methoxypropanoate
-
 ?
3.1.2.12 fluorescein-3',6'-bis(oxy)methylene bis(2-methoxypropanoate) + H2O
-
 Staphylococcus aureus PS 47 fluorescein-3'-oxymethyl 2-methoxypropanoate + 2-methoxypropanoate
-
 ?
3.1.2.12 fluorescein-3',6'-bis(oxy)methylene bis(ethoxyacetate) + H2O
-
 Staphylococcus aureus fluorescein-3'-yoxymethyl ethoxyacetate + ethoxyacetate
-
 ?
3.1.2.12 fluorescein-3',6'-bis(oxy)methylene bis(ethoxyacetate) + H2O
-
 Staphylococcus aureus PS 47 fluorescein-3'-yoxymethyl ethoxyacetate + ethoxyacetate
-
 ?
3.1.2.12 fluorescein-3',6'-bis(oxy)methylene bis(methoxyacetate) + H2O
-
 Staphylococcus aureus fluorescein-3'-oxymethyl methoxyacetate + methoxyacetate
-
 ?
3.1.2.12 fluorescein-3',6'-bis(oxy)methylene bis(propoxyacetate) + H2O
-
 Staphylococcus aureus fluorescein-3'-oxymethyl propoxyacetate + propoxyacetate
-
 ?
3.1.2.12 fluorescein-3',6'-bis(oxy)methylene bis[(methylsulfanyl)acetate] + H2O
-
 Staphylococcus aureus fluorescein-3'-oxymethyl (methylsulfanyl)acetate + (methylsulfanyl)acetate
-
 ?
3.1.2.12 fluorescein-3',6'-bis(oxy)methylene bis[[(propan-2-yl)sulfanyl]acetate] + H2O
-
 Staphylococcus aureus fluorescein-3'-oxymethyl [(propan-2-yl)sulfanyl]acetate + [(propan-2-yl)sulfanyl]acetate
-
 ?
3.1.2.12 fluorescein-3',6'-bis(oxy)methylene dibutanoate + H2O
-
 Staphylococcus aureus fluorescein-3'-oxymethyl butanoate + butanoate
-
 ?
3.1.2.12 fluorescein-3',6'-bis(oxy)methylene dihexanoate + H2O
-
 Staphylococcus aureus fluorescein-3'-oxymethyl hexanoate + hexanoate
-
 ?
3.1.2.12 fluorescein-3',6'-bis(oxy)methylene dipentanoate + H2O
-
 Staphylococcus aureus fluorescein-3'-oxymethyl pentanoate + pentanoate
-
 ?
3.1.2.12 additional information enzyme shows modest activity with substrates 4-nitrophenyl acetate, 4-nitrophenyl butanoate, but not with 4-nitrophenyl trimethylacetate Staphylococcus aureus ?
-
-
3.1.2.12 additional information enzyme shows modest activity with substrates 4-nitrophenyl acetate, 4-nitrophenyl butanoate, but not with 4-nitrophenyl trimethylacetate Staphylococcus aureus PS 47 ?
-
-

Subunits

EC Number Subunits Comment Organism
3.1.2.6 ? x * 23300, calculated from sequence and SDS-PAGE Staphylococcus aureus
3.1.2.12 ? x * 29500, calculated from sequence and SDS-PAGE Staphylococcus aureus

Synonyms

EC Number Synonyms Comment Organism
3.1.2.6 A7Q05_1268
-
 Staphylococcus aureus
3.1.2.6 GloB
-
 Staphylococcus aureus
3.1.2.12 FrmB
-
 Staphylococcus aureus
3.1.2.12 SAOUHSC_02962
-
 Staphylococcus aureus

General Information

EC Number General Information Comment Organism
3.1.2.6 metabolism GloB activates the prodrug bis(pivaloyloxymethyl) (1-hydroxy-2-oxopiperidin-3-yl)phosphonate. Mutation of GloB renders Staphylococcus aureus sensitive to bis(pivaloyloxymethyl) (1-hydroxy-2-oxopiperidin-3-yl)phosphonate Staphylococcus aureus
3.1.2.6 physiological function GloB is active toward oxygen ethers. GloB has the highest activity against short-chain ethers, with some tolerance for branching at the first carbon beyond the ester carbonyl group. GloB exhibits a strong preference for oxygen at the beta-position to the carbonyl over the gamma-position but is indifferent to the positioning of sulfur Staphylococcus aureus
3.1.2.12 metabolism FrmB activates the prodrug bis(pivaloyloxymethyl) (1-hydroxy-2-oxopiperidin-3-yl)phosphonate. Mutation of FrmB renders Staphylococcus aureus sensitive to bis(pivaloyloxymethyl) (1-hydroxy-2-oxopiperidin-3-yl)phosphonate Staphylococcus aureus
3.1.2.12 physiological function FrmB has the highest activity toward oxygen ethers. FrmB hydrolyzes unbranched substrates with little regard for chain length or the end-of-chain bulk within the tested substrates. Branching at the position following the ester carbonyl is deleterious to FrmB activity. When oxygen is included in the chain, positioning at the beta-position to the carbonyl is strongly preferred over the gamma-position Staphylococcus aureus