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Literature summary for 3.5.2.6 extracted from

  • Badarau, A.; Llinas, A.; Laws, A.P.; Damblon, C.; Page, M.I.
    Inhibitors of metallo-beta-lactamase generated from beta-lactam antibiotics (2005), Biochemistry, 44, 8578-8589.
    View publication on PubMed
Search for more literature for 3.5.2.6

Inhibitors

Inhibitors Comment Organism Structure
(2R,3E)-2-([amino(phenyl)acetyl]amino)-3-[(1,2-dihydroxy-3-mercaptoprop-1-en-1-yl)imino]propanoic acid competitive Bacillus cereus
(2Z)-2-(((E)-2-carboxy-2-[(2-thienylacetyl)amino]vinyl)imino)-3-mercaptobut-3-enoic acid
-
 Bacillus cereus
additional information hydrolysis of cephalosporin beta-lactam antibiotics generates dihydrothiazines which subsequently undergo isomerization at C6 by C-S bond cleavage and through the intermediacy of a thiol. These thiols can be trapped by the beta-lactamase from Bacillus cereus, causing inhibition of the enzyme. The rate of production of the thiol corresponds to the rate of inhibition, and the inhibition constants are in the micromolar range but vary with the nature of the cephalosporin derivative. The thiol binds to the zinc ion, which in turn perturbs the metal-bound histidines. Inhibition is slowly removed as the thiol becomes oxidized or undergoes further degradation. The thiol intermediate generated from cephalothin is a slow binding inhibitor. There is no observed inhibition from the analogous degradation products from penicillins Bacillus cereus

Organism

Organism UniProt Comment Textmining
Bacillus cereus
-
-
-

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
cephalexin + H2O
-
 Bacillus cereus (2R)-2-[(R)-[[(2R)-2-amino-2-phenylacetyl]amino](carboxy)methyl]-5-methyl-3,6-dihydro-2H-1,3-thiazine-4-carboxylic acid
-
 ?
nitrocefin + H2O
-
 Bacillus cereus (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
metallo-beta-lactamase BcII
-
 Bacillus cereus

Ki Value [mM]

Ki Value [mM] Ki Value maximum [mM] Inhibitor Comment Organism Structure
additional information
-
 additional information Ki for (2R,3E)-2-([amino(phenyl)acetyl]amino)-3-[(1,2-dihydroxy-3-mercaptoprop-1-en-1-yl)imino]propanoic acid is less than 40 nM Bacillus cereus
0.00374
-
 (2Z)-2-(((E)-2-carboxy-2-[(2-thienylacetyl)amino]vinyl)imino)-3-mercaptobut-3-enoic acid
-
 Bacillus cereus