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Literature summary for 3.5.2.6 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

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

Organism

Organism UniProt Comment Textmining
Enterobacter cloacae
-
-
-
Enterobacter cloacae P99
-
-
-
Escherichia coli
-
-
-

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
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
-
?
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
-
?
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

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

Ki Value [mM]

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