The role of a beta-proton transfer donor in the degradation of benzylpenicillin

Show simple item record Llinás, A. Vilanova Canet, Bartolomé Muñoz Izquierdo, Francisco Donoso Pardo, Josefa Laurentina 2018-11-22T12:11:45Z
dc.description.abstract [eng] The thiolysis mechanism of benzylpenicillin has been determined by 1H NMR and HPLC. The degradation of benzylpenicillin was accelerated when the thiol used presented a -group capable of acting as a general acid catalyst, such as -monothioglycerol, 2-mercaptoethanol and mercaptoethylamine. With these thiols, after the formation of the thioester, an intramolecular acyl transfer reaction occurs at a pH far below the pKa of the group acting as a general acid catalyst, which shows that the proton transfer has already occurred, probably in a concerted mechanism with the nucleophilic attack. Rate constants were calculated. The system can be taken as a simple model of the general acid catalyst in serine and cysteine proteases.
dc.format application/pdf
dc.relation.ispartof Journal of Molecular Catalysis, 2001, vol. 175, p. 3-16
dc.rights , 2001
dc.subject.classification 54 - Química
dc.subject.other 54 - Chemistry. Crystallography. Mineralogy
dc.title The role of a beta-proton transfer donor in the degradation of benzylpenicillin
dc.type info:eu-repo/semantics/article 2018-11-22T12:11:45Z info:eu-repo/date/embargoEnd/2075-01-01
dc.embargo 2075-01-01
dc.rights.accessRights info:eu-repo/semantics/embargoedAccess

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