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Literature summary extracted from

  • Perumal, S.K.; Pratt, R.F.
    Synthesis and evaluation of ketophosph(on)ates as beta-lactamase inhibitors (2006), J. Org. Chem., 71, 4778-4785.
    View publication on PubMed

Inhibitors

EC Number Inhibitors Comment Organism Structure
3.5.2.6 (R)-3-(N-benzyloxycarbonylamino)-2-oxo-butylphosphate
-
 Enterobacter cloacae
3.5.2.6 (R)-3-(N-benzyloxycarbonylamino)-2-oxo-butylphosphate
-
 Escherichia coli
3.5.2.6 (RS)-4-(N-benzyloxycarbonyl)amino-3-oxo-2-butylphosphate
-
 Enterobacter cloacae
3.5.2.6 (RS)-4-(N-benzyloxycarbonyl)amino-3-oxo-2-butylphosphate
-
 Escherichia coli
3.5.2.6 3-(N-benzyloxycarbonyl)amino-2-oxopropylphenylphosphonate
-
 Enterobacter cloacae
3.5.2.6 3-(N-benzyloxycarbonyl)amino-2-oxopropylphenylphosphonate
-
 Escherichia coli
3.5.2.6 3-(N-benzyloxycarbonyl)amino-2-oxopropylphosphate
-
 Enterobacter cloacae
3.5.2.6 3-(N-benzyloxycarbonyl)amino-2-oxopropylphosphate
-
 Escherichia coli
3.5.2.6 3-(N-benzyloxycarbonyl)amino-2-oxopropylphosphonate
-
 Enterobacter cloacae
3.5.2.6 3-(N-benzyloxycarbonyl)amino-2-oxopropylphosphonate
-
 Escherichia coli
3.5.2.6 4-(N-benzyloxycarbonyl)amino-3-oxobutylphosphonate
-
 Enterobacter cloacae
3.5.2.6 4-(N-benzyloxycarbonyl)amino-3-oxobutylphosphonate
-
 Escherichia coli
3.5.2.6 ethyl 3-(benzyloxycarbonyl)amino-2-oxo-1,1-difluoropropylphosphonate
-
 Enterobacter cloacae
3.5.2.6 ethyl 3-(benzyloxycarbonyl)amino-2-oxo-1,1-difluoropropylphosphonate
-
 Escherichia coli
3.5.2.6 methyl 3-(N-benzyloxycarbonyl)amino-2-oxo-1-propylphosphate
-
 Enterobacter cloacae
3.5.2.6 methyl 3-(N-benzyloxycarbonyl)amino-2-oxo-1-propylphosphate
-
 Escherichia coli
3.5.2.6 N-[N'-(benzyloxycarbonyl)aminoacetyl]amino-methylphosphonate
-
 Enterobacter cloacae
3.5.2.6 N-[N'-(benzyloxycarbonyl)aminoacetyl]amino-methylphosphonate
-
 Escherichia coli
3.5.2.6 phenyl 3-(N-benzyloxycarbonyl)amino-2-oxopropylphosphate
-
 Enterobacter cloacae
3.5.2.6 phenyl 3-(N-benzyloxycarbonyl)amino-2-oxopropylphosphate
-
 Escherichia coli
3.5.2.6 phenyl 3-(N-benzyloxycarbonyl)amino-2-oxopropylphosphonate
-
 Enterobacter cloacae
3.5.2.6 phenyl 3-(N-benzyloxycarbonyl)amino-2-oxopropylphosphonate
-
 Escherichia coli

Organism

EC Number Organism UniProt Comment Textmining
3.5.2.6 Enterobacter cloacae
-
-
-
3.5.2.6 Enterobacter cloacae P99
-
-
-
3.5.2.6 Escherichia coli
-
-
-

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
3.5.2.6 7beta-aminocephalosporanic acid + H2O
-
 Enterobacter cloacae (2R)-5-[(acetyloxy)methyl]-2-[(R)-amino(carboxy)methyl]-3,6-dihydro-2H-1,3-thiazine-4-carboxylic acid
-
 ?
3.5.2.6 7beta-aminocephalosporanic acid + H2O
-
 Enterobacter cloacae P99 (2R)-5-[(acetyloxy)methyl]-2-[(R)-amino(carboxy)methyl]-3,6-dihydro-2H-1,3-thiazine-4-carboxylic acid
-
 ?
3.5.2.6 7beta-[(thien-2-yl)acetamido]-3-[(4-nitro-3-carboxyphenylthio)methyl]-3-cephem-4-carboxylic acid + H2O
-
 Escherichia coli (2R)-2-[(R)-carboxy{(E)-[1-hydroxy-2-(thiophen-2-yl)ethylidene]amino}methyl]-5-{[(3-carboxy-4-nitrophenyl)sulfanyl]methyl}-3,6-dihydro-2H-1,3-thiazine-4-carboxylic acid
-
 ?

Synonyms

EC Number Synonyms Comment Organism
3.5.2.6 beta-lactamase OXA-1
-
 Escherichia coli
3.5.2.6 beta-lactamase OXA-10
-
 Escherichia coli
3.5.2.6 beta-lactamase P99
-
 Enterobacter cloacae

Ki Value [mM]

EC Number Ki Value [mM] Ki Value maximum [mM] Inhibitor Comment Organism Structure
3.5.2.6 0.077
-
 phenyl 3-(N-benzyloxycarbonyl)amino-2-oxopropylphosphonate
-
 Escherichia coli
3.5.2.6 0.088
-
 (RS)-4-(N-benzyloxycarbonyl)amino-3-oxo-2-butylphosphate
-
 Escherichia coli
3.5.2.6 0.1
-
 3-(N-benzyloxycarbonyl)amino-2-oxopropylphosphate
-
 Escherichia coli
3.5.2.6 0.11
-
 phenyl 3-(N-benzyloxycarbonyl)amino-2-oxopropylphosphate
-
 Escherichia coli
3.5.2.6 0.13
-
 phenyl 3-(N-benzyloxycarbonyl)amino-2-oxopropylphosphonate
-
 Escherichia coli
3.5.2.6 0.13
-
 phenyl 3-(N-benzyloxycarbonyl)amino-2-oxopropylphosphate
-
 Escherichia coli
3.5.2.6 0.15
-
 3-(N-benzyloxycarbonyl)amino-2-oxopropylphenylphosphonate
-
 Escherichia coli
3.5.2.6 0.15
-
 3-(N-benzyloxycarbonyl)amino-2-oxopropylphosphonate
-
 Escherichia coli
3.5.2.6 0.19
-
 3-(N-benzyloxycarbonyl)amino-2-oxopropylphenylphosphonate
-
 Escherichia coli
3.5.2.6 0.2
-
 (RS)-4-(N-benzyloxycarbonyl)amino-3-oxo-2-butylphosphate
-
 Escherichia coli
3.5.2.6 0.24
-
 methyl 3-(N-benzyloxycarbonyl)amino-2-oxo-1-propylphosphate
-
 Escherichia coli
3.5.2.6 0.3
-
 (R)-3-(N-benzyloxycarbonylamino)-2-oxo-butylphosphate
-
 Escherichia coli
3.5.2.6 0.36
-
 (R)-3-(N-benzyloxycarbonylamino)-2-oxo-butylphosphate
-
 Escherichia coli
3.5.2.6 0.43
-
 N-[N'-(benzyloxycarbonyl)aminoacetyl]amino-methylphosphonate
-
 Escherichia coli
3.5.2.6 0.47
-
 4-(N-benzyloxycarbonyl)amino-3-oxobutylphosphonate
-
 Escherichia coli
3.5.2.6 0.6
-
 3-(N-benzyloxycarbonyl)amino-2-oxopropylphosphate
-
 Escherichia coli
3.5.2.6 0.6
-
 4-(N-benzyloxycarbonyl)amino-3-oxobutylphosphonate
-
 Escherichia coli
3.5.2.6 0.7
-
 phenyl 3-(N-benzyloxycarbonyl)amino-2-oxopropylphosphate
-
 Enterobacter cloacae
3.5.2.6 0.73
-
 3-(N-benzyloxycarbonyl)amino-2-oxopropylphosphonate
-
 Enterobacter cloacae
3.5.2.6 0.93
-
 ethyl 3-(benzyloxycarbonyl)amino-2-oxo-1,1-difluoropropylphosphonate
-
 Escherichia coli
3.5.2.6 0.93
-
 N-[N'-(benzyloxycarbonyl)aminoacetyl]amino-methylphosphonate
-
 Enterobacter cloacae
3.5.2.6 0.95
-
 ethyl 3-(benzyloxycarbonyl)amino-2-oxo-1,1-difluoropropylphosphonate
-
 Enterobacter cloacae
3.5.2.6 0.97
-
 (RS)-4-(N-benzyloxycarbonyl)amino-3-oxo-2-butylphosphate
-
 Enterobacter cloacae
3.5.2.6 1.13
-
 methyl 3-(N-benzyloxycarbonyl)amino-2-oxo-1-propylphosphate
-
 Enterobacter cloacae
3.5.2.6 1.23
-
 4-(N-benzyloxycarbonyl)amino-3-oxobutylphosphonate
-
 Enterobacter cloacae
3.5.2.6 1.59
-
 phenyl 3-(N-benzyloxycarbonyl)amino-2-oxopropylphosphonate
-
 Enterobacter cloacae
3.5.2.6 2
-
 3-(N-benzyloxycarbonyl)amino-2-oxopropylphosphate
-
 Enterobacter cloacae
3.5.2.6 2.1
-
 (R)-3-(N-benzyloxycarbonylamino)-2-oxo-butylphosphate
-
 Enterobacter cloacae
3.5.2.6 5
-
 3-(N-benzyloxycarbonyl)amino-2-oxopropylphenylphosphonate
-
 Enterobacter cloacae