Kinetics and Mechanism of Zinc Ion-Mediated Degradation of Cephalosporins in Tromethamine Solution.

Autor: Tomida, Hisao, Kohashi, Kazuya, Tsuruta, Yasuto, Kiryu, Setsuo, Schwartz, Michael
Zdroj: Pharmaceutical Research; Jun1987, Vol. 4 Issue 3, p214-219, 6p
Abstrakt: Earlier studies of the hydrolysis and aminolysis of penicillin, in the presence of zinc ion and tromethamine (Tris), revealed a very rapid catalysis mediated by a ternary complex in which the metal ion brought the reactants into close proximity in a suitable configuration for reaction. In the present work similar studies with a group of cephalosporins show not only much slower rates of reaction but a different mechanism in which the zinc ion-tromethamine complex functions as a nucleophile in a bimolecular reaction. Evidence for the differences in mechanism includes not only the different dependence of rate upon tromethamine concentration, but comparable rates of reaction of methyl esters of a penicillin and a cephalosporin and the reaction products observed by high-performance liquid chromatography. [ABSTRACT FROM AUTHOR]
Databáze: Complementary Index