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Literature summary for 3.5.2.6 extracted from

  • Perumal, S.K.; Adediran, S.A.; Pratt, R.F.
    beta -Ketophosphonates as beta -lactamase inhibitors: Intramolecular cooperativity between the hydrophobic subsites of a class D beta -lactamase (2008), Bioorg. Med. Chem., 16, 6987-6994.
    View publication on PubMed

Inhibitors

Inhibitors Comment Organism Structure
additional information beta-ketophosphonates are less effective against OXA-10 enzyme, effective inhibitors of the class D OXA-1 enzyme and the class C P99 enzyme Enterobacter cloacae
additional information beta-ketophosphonates are less effective against OXA-10 enzyme, effective inhibitors of the class D OXA-1 enzyme and the class C P99 enzyme; beta-ketophosphonates are less effective against OXA-10 enzyme, effective inhibitors of the class D OXA-1 enzyme and the class C P99 enzyme; beta-ketophosphonates are less effective against OXA-10 enzyme, effective inhibitors of the class D OXA-1 enzyme and the class C P99 enzyme Escherichia coli
sodium benzyl (2-hydroxy-2-phenylethyl)phosphonate
-
Enterobacter cloacae
sodium benzyl (2-hydroxy-2-phenylethyl)phosphonate
-
Escherichia coli
sodium benzyl (2-oxo-2-phenylethyl)phosphonate
-
Enterobacter cloacae
sodium benzyl (2-oxo-2-phenylethyl)phosphonate
-
Escherichia coli
sodium benzyl 2-(1',3'-benzothiazol-2'-yl)-2-oxo-ethylphosphonate
-
Enterobacter cloacae
sodium benzyl 2-(1',3'-benzothiazol-2'-yl)-2-oxo-ethylphosphonate
-
Escherichia coli
sodium benzyl [2-(biphenyl-4-yl)-2-hydroxyethyl]phosphonate
-
Enterobacter cloacae
sodium benzyl [2-(biphenyl-4-yl)-2-hydroxyethyl]phosphonate
-
Escherichia coli
sodium benzyl [2-(biphenyl-4-yl)-2-oxoethyl]phosphonate
-
Enterobacter cloacae
sodium benzyl [2-(biphenyl-4-yl)-2-oxoethyl]phosphonate
-
Escherichia coli
sodium benzyl [2-oxo-2-(2-oxo-2,3-dihydro-1,3-benzoxazol-6-yl)ethyl]phosphonate
-
Enterobacter cloacae
sodium benzyl [2-oxo-2-(2-oxo-2,3-dihydro-1,3-benzoxazol-6-yl)ethyl]phosphonate
-
Escherichia coli
sodium benzyl {2-[3-(2-chlorophenyl)-5-methyl-1,2-oxazol-4-yl]-2-oxoethyl}phosphonate
-
Enterobacter cloacae
sodium benzyl {2-[3-(2-chlorophenyl)-5-methyl-1,2-oxazol-4-yl]-2-oxoethyl}phosphonate
-
Escherichia coli
sodium biphenyl-4-ylmethyl (2-oxo-2-phenylethyl)phosphonate
-
Enterobacter cloacae
sodium biphenyl-4-ylmethyl (2-oxo-2-phenylethyl)phosphonate
-
Escherichia coli
sodium biphenyl-4-ylmethyl [2-(biphenyl-4-yl)-2-oxoethyl]phosphonate
-
Enterobacter cloacae
sodium biphenyl-4-ylmethyl [2-(biphenyl-4-yl)-2-oxoethyl]phosphonate
-
Escherichia coli
sodium phenyl (2-oxo-2-phenylethyl)phosphonate
-
Enterobacter cloacae
sodium phenyl (2-oxo-2-phenylethyl)phosphonate
-
Escherichia coli
sodium phenyl [2-(biphenyl-4-yl)-2-oxoethyl]phosphonate
-
Enterobacter cloacae
sodium phenyl [2-(biphenyl-4-yl)-2-oxoethyl]phosphonate
-
Escherichia coli
sodium phenyl [2-oxo-2-(pentafluorophenyl)ethyl]phosphonate
-
Enterobacter cloacae
sodium phenyl [2-oxo-2-(pentafluorophenyl)ethyl]phosphonate
-
Escherichia coli

KM Value [mM]

KM Value [mM] KM Value Maximum [mM] Substrate Comment Organism Structure
0.0076
-
nitrocefin pH 7.5, 25°C Escherichia coli
0.0226
-
nitrocefin pH 7.5, 25°C Escherichia coli
0.086
-
nitrocefin pH 7.5, 25°C Escherichia coli
0.12
-
cephalothin pH 7.5, 25°C Escherichia coli
0.29
-
7-aminocephalosporanic acid pH 7.5, 25°C Enterobacter cloacae

Organism

Organism UniProt Comment Textmining
Enterobacter cloacae Q59401 P99
-
Enterobacter cloacae P99 Q59401 P99
-
Escherichia coli
-
-
-
Escherichia coli P13661 class D OXA-1 beta-lactamase, E. coli
-
Escherichia coli P62593 class A TEM-2 enzyme Escherichia coli
-

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
7alpha-aminocephalosporanic acid + H2O
-
Enterobacter cloacae (2R)-5-[(acetyloxy)methyl]-2-[(S)-amino(carboxy)methyl]-3,6-dihydro-2H-1,3-thiazine-4-carboxylic acid
-
?
7alpha-aminocephalosporanic acid + H2O
-
Enterobacter cloacae P99 (2R)-5-[(acetyloxy)methyl]-2-[(S)-amino(carboxy)methyl]-3,6-dihydro-2H-1,3-thiazine-4-carboxylic acid
-
?
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
-
?
cephalothin + H2O
-
Escherichia coli (2R)-5-[(acetyloxy)methyl]-2-[(R)-carboxy[(thiophen-2-ylacetyl)amino]methyl]-3,6-dihydro-2H-1,3-thiazine-4-carboxylic acid
-
?
nitrocefin + H2O
-
Escherichia coli (2R)-2-{(R)-carboxy[2-(thiophen-2-yl)acetamido]methyl}-5-[(E)-2-(2,4-dinitrophenyl)ethenyl]-3,6-dihydro-2H-1,3-thiazine-4-carboxylic acid
-
?

Synonyms

Synonyms Comment Organism
beta-lactamase
-
Escherichia coli
beta-lactamase
-
Enterobacter cloacae
class A TEM-2 enzyme
-
Escherichia coli
class C beta-lactamase
-
Enterobacter cloacae
class D OXA-1 beta-lactamase
-
Escherichia coli
OXA-10 enzyme
-
Escherichia coli

Temperature Optimum [°C]

Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
25
-
assay at Escherichia coli
25
-
assay at Enterobacter cloacae

pH Optimum

pH Optimum Minimum pH Optimum Maximum Comment Organism
7.5
-
assay at Escherichia coli
7.5
-
assay at Enterobacter cloacae

Ki Value [mM]

Ki Value [mM] Ki Value maximum [mM] Inhibitor Comment Organism Structure
0.006
-
sodium biphenyl-4-ylmethyl [2-(biphenyl-4-yl)-2-oxoethyl]phosphonate pH 7.5, 25°C Escherichia coli
0.024
-
sodium benzyl 2-(1',3'-benzothiazol-2'-yl)-2-oxo-ethylphosphonate pH 7.5, 25°C Enterobacter cloacae
0.07
-
sodium benzyl [2-oxo-2-(2-oxo-2,3-dihydro-1,3-benzoxazol-6-yl)ethyl]phosphonate pH 7.5, 25°C Enterobacter cloacae
0.074
-
sodium biphenyl-4-ylmethyl [2-(biphenyl-4-yl)-2-oxoethyl]phosphonate pH 7.5, 25°C Enterobacter cloacae
0.1
-
sodium phenyl [2-(biphenyl-4-yl)-2-oxoethyl]phosphonate pH 7.5, 25°C Enterobacter cloacae
0.14
-
sodium phenyl [2-(biphenyl-4-yl)-2-oxoethyl]phosphonate pH 7.5, 25°C Escherichia coli
0.15
-
sodium benzyl (2-oxo-2-phenylethyl)phosphonate pH 7.5, 25°C Escherichia coli
0.17
-
sodium benzyl 2-(1',3'-benzothiazol-2'-yl)-2-oxo-ethylphosphonate pH 7.5, 25°C Escherichia coli
0.19
-
sodium benzyl [2-(biphenyl-4-yl)-2-oxoethyl]phosphonate pH 7.5, 25°C Enterobacter cloacae
0.2
-
sodium phenyl (2-oxo-2-phenylethyl)phosphonate pH 7.5, 25°C Enterobacter cloacae
0.2
-
sodium biphenyl-4-ylmethyl [2-(biphenyl-4-yl)-2-oxoethyl]phosphonate pH 7.5, 25°C Escherichia coli
0.2
-
sodium biphenyl-4-ylmethyl (2-oxo-2-phenylethyl)phosphonate pH 7.5, 25°C Escherichia coli
0.23
-
sodium benzyl [2-(biphenyl-4-yl)-2-oxoethyl]phosphonate pH 7.5, 25°C Escherichia coli
0.26
-
sodium benzyl [2-(biphenyl-4-yl)-2-hydroxyethyl]phosphonate pH 7.5, 25°C Enterobacter cloacae
0.27
-
sodium benzyl [2-oxo-2-(2-oxo-2,3-dihydro-1,3-benzoxazol-6-yl)ethyl]phosphonate pH 7.5, 25°C Escherichia coli
0.3
-
sodium benzyl [2-(biphenyl-4-yl)-2-hydroxyethyl]phosphonate pH 7.5, 25°C Escherichia coli
0.35
-
sodium phenyl [2-oxo-2-(pentafluorophenyl)ethyl]phosphonate pH 7.5, 25°C Enterobacter cloacae
0.38
-
sodium phenyl [2-oxo-2-(pentafluorophenyl)ethyl]phosphonate pH 7.5, 25°C Escherichia coli
0.43
-
sodium benzyl {2-[3-(2-chlorophenyl)-5-methyl-1,2-oxazol-4-yl]-2-oxoethyl}phosphonate pH 7.5, 25°C Escherichia coli
0.44
-
sodium benzyl (2-hydroxy-2-phenylethyl)phosphonate pH 7.5, 25°C Escherichia coli
0.475
-
sodium phenyl [2-oxo-2-(pentafluorophenyl)ethyl]phosphonate pH 7.5, 25°C Escherichia coli
0.64
-
sodium benzyl (2-oxo-2-phenylethyl)phosphonate pH 7.5, 25°C Escherichia coli
0.67
-
sodium benzyl (2-oxo-2-phenylethyl)phosphonate pH 7.5, 25°C Enterobacter cloacae
0.92
-
sodium phenyl [2-(biphenyl-4-yl)-2-oxoethyl]phosphonate pH 7.5, 25°C Escherichia coli
1
-
sodium benzyl [2-(biphenyl-4-yl)-2-oxoethyl]phosphonate pH 7.5, 25°C Escherichia coli
1
-
sodium benzyl {2-[3-(2-chlorophenyl)-5-methyl-1,2-oxazol-4-yl]-2-oxoethyl}phosphonate pH 7.5, 25°C Escherichia coli
1
-
sodium benzyl (2-hydroxy-2-phenylethyl)phosphonate pH 7.5, 25°C Escherichia coli
1
-
sodium benzyl [2-(biphenyl-4-yl)-2-hydroxyethyl]phosphonate pH 7.5, 25°C Escherichia coli
1
-
sodium phenyl [2-oxo-2-(pentafluorophenyl)ethyl]phosphonate above, pH 7.5, 25°C Escherichia coli
1
-
sodium benzyl (2-oxo-2-phenylethyl)phosphonate above, pH 7.5, 25°C Escherichia coli
1
-
sodium benzyl [2-(biphenyl-4-yl)-2-oxoethyl]phosphonate above, pH 7.5, 25°C Escherichia coli
1
-
sodium phenyl (2-oxo-2-phenylethyl)phosphonate above, pH 7.5, 25°C Escherichia coli
1
-
sodium benzyl {2-[3-(2-chlorophenyl)-5-methyl-1,2-oxazol-4-yl]-2-oxoethyl}phosphonate above, pH 7.5, 25°C Enterobacter cloacae
1
-
sodium biphenyl-4-ylmethyl (2-oxo-2-phenylethyl)phosphonate above, pH 7.5, 25°C Escherichia coli
1.05
-
sodium phenyl (2-oxo-2-phenylethyl)phosphonate pH 7.5, 25°C Escherichia coli
1.08
-
sodium benzyl (2-hydroxy-2-phenylethyl)phosphonate pH 7.5, 25°C Enterobacter cloacae
1.5
-
sodium benzyl [2-oxo-2-(2-oxo-2,3-dihydro-1,3-benzoxazol-6-yl)ethyl]phosphonate pH 7.5, 25°C Escherichia coli
3600
-
sodium benzyl 2-(1',3'-benzothiazol-2'-yl)-2-oxo-ethylphosphonate pH 7.5, 25°C Escherichia coli