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Literature summary for 3.5.2.6 extracted from

  • Eidam, O.; Romagnoli, C.; Caselli, E.; Babaoglu, K.; Pohlhaus, D.T.; Karpiak, J.; Bonnet, R.; Shoichet, B.K.; Prati, F.
    Design, synthesis, crystal structures, and antimicrobial activity of sulfonamide boronic acids as beta-lactamase inhibitors (2010), J. Med. Chem., 53, 7852-7863.
    View publication on PubMedView publication on EuropePMC

Crystallization (Commentary)

Crystallization (Comment) Organism
in complex with ([(benzylsulfonyl)amino]methyl)boronic acid, 4-([[(dihydroxyboranyl)methyl]sulfamoyl]methyl)benzoic acid, and 3-[(2R)-2-[(benzylsulfonyl)amino]-2-(dihydroxyboranyl)ethyl]benzoic acid, to 1.6, 1.8 and 1.6 A resolution, respectively. The sulfonamides have a highly distinct structure-activity relationship from the carboxamides, with high ligand efficiencies, and Ki values down to 25 nM and up to 23 times better for smaller analogs. Conversely, Ki values are 10 to 20 times worse for larger molecules than in the carboxamide congener series. X-ray crystal structures suggest that this altered structure-activity relationship results from the different geometry and polarity of the sulfonamide versus the carboxamide Escherichia coli

Inhibitors

Inhibitors Comment Organism Structure
([(benzylsulfonyl)amino]methyl)boronic acid
-
Escherichia coli
([[(2-ethoxynaphthalen-1-yl)carbonyl]amino]methyl)boronic acid
-
Escherichia coli
3-[(2R)-2-(dihydroxyboranyl)-2-[[(thiophen-2-ylmethyl)sulfonyl]amino]ethyl]benzoic acid
-
Escherichia coli
3-[(2R)-2-[(benzylsulfonyl)amino]-2-(dihydroxyboranyl)ethyl]benzoic acid
-
Escherichia coli
4-([[(dihydroxyboranyl)methyl]sulfamoyl]methyl)benzoic acid
-
Escherichia coli

Organism

Organism UniProt Comment Textmining
Escherichia coli P00811
-
-

Synonyms

Synonyms Comment Organism
AmpC
-
Escherichia coli

Ki Value [mM]

Ki Value [mM] Ki Value maximum [mM] Inhibitor Comment Organism Structure
0.000001
-
3-[(2R)-2-(dihydroxyboranyl)-2-[[(thiophen-2-ylmethyl)sulfonyl]amino]ethyl]benzoic acid pH 6.5, 22°C Escherichia coli
0.000025
-
4-([[(dihydroxyboranyl)methyl]sulfamoyl]methyl)benzoic acid pH 6.5, 22°C Escherichia coli
0.000033
-
([[(2-ethoxynaphthalen-1-yl)carbonyl]amino]methyl)boronic acid pH 6.5, 22°C Escherichia coli
0.00007
-
([(benzylsulfonyl)amino]methyl)boronic acid pH 6.5, 22°C Escherichia coli
0.00043
-
3-[(2R)-2-[(benzylsulfonyl)amino]-2-(dihydroxyboranyl)ethyl]benzoic acid pH 6.5, 22°C Escherichia coli