Reference : Stability of D-5,5-dimethyl-delta2-thiazoline-4-carboxylic acid in relation to its po...
Scientific journals : Article
Life sciences : Microbiology
Life sciences : Biochemistry, biophysics & molecular biology
http://hdl.handle.net/2268/91724
Stability of D-5,5-dimethyl-delta2-thiazoline-4-carboxylic acid in relation to its possible occurrence as a degradation product of penicillin by the exocellular DD-carboxypeptidase-transpeptidase from Streptomyces R61 and the membrane-bound dd-carboxypeptidase from Bacillus stearothermophilus
English
Adriaens, Paul [Université Catholique de Louvain - UCL > Rega Instituut > > >]
Meesschaert, Boudewijn [Université Catholique de Louvain - UCL > Rega Instituut > > >]
Frère, Jean-Marie mailto [Université de Liège - ULg > Institut de Botanique > Service de Microbiologie > >]
Vanderhaeghe, Hubert [> > > >]
Degelaen, Jacques [> > > >]
Ghuysen, Jean-Marie [Université de Liège - ULg > Institut de Botanique > Service de Microbiologie > >]
Eyssen, Hendrick [> > > >]
25-Apr-1978
Journal of Biological Chemistry
American Society for Biochemistry and Molecular Biology
253
10
3660-3665
Yes (verified by ORBi)
International
0021-9258
1083-351X
Baltimore
MD
[en] acyltransferases/*metabolism ; carboxypeptidases/*metabolism ; cell membrane/enzymology ; circular dichroism ; drug stability ; geobacillus stearothermophilus/*enzymology ; kinetics ; mass spectrometry ; penicillins ; peptidyl transferases/*metabolism ; spectrophotometry, ultraviolet ; streptomyces/*enzymology ; thiazoles
[en] The stability of D-5,5-dimethyl-delta2-thiazoline-4-carboxylic acid has been studied under various conditions. In 10 mM cacodylate, pH 6.5, and at 55 degrees C, D-5,5-dimethyl-delta2-thiazoline-4-carboxylic acid (at concentrations lower than 1 mM) is hydrolyzed into N-formyl-D-penicillamine with a half-life of 3 to 4 min. On this basis, it is very unlikely that D-5,5-dimethyl-delta2-thiazoline-4-carboxylic acid could be one of the end products resulting from the cleavage of benzylpenicillin by the DD-carboxypeptidase of Bacillus stearothermophilus (as reported by Hammarstrom and Strominger (1976) J. Biol. Chem. 251, 7947--7949). In 3 mM phosphate, pH 7.5, and at 37 degrees C, D-5,5-dimethyl-delta2-thiazoline-4-carboxylic acid (at concentrations lower than 1 mM) has a half-life of 45 min. On the basis of kinetic experiments carried out under these conditions with phenoxymethylpenicillin and the DD-carboxypeptidase-transpeptidase of Streptomyces R61, it is concluded that the primary product which arises from the thiazolidine moiety of the antibiotic molecule and gives rise to N-formyl-D-penicillamine, has a half-life of 10 min, a value which is not compatible with the hypothesis that D-5,5-dimethyl-delta2-thiazoline-4-carboxylic acid would be an intermediate involved in the fragmentation pathway.
National Institutes of Health - NIH
Researchers ; Professionals
http://hdl.handle.net/2268/91724

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