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Aromatic substitution reaction of 2-chloropyridines catalyzed by microsomal glutathione S-transferase 1.

Drug metabolism and disposition: the biological fate of chemicals (2009-06-23)
Kazuko Inoue, Tomoyuki Ohe, Kenichi Mori, Takeshi Sagara, Yasuyuki Ishii, Masato Chiba
ABSTRACT

We investigated the substitution reaction of a series of 2-chloropyridine derivatives catalyzed by rat liver microsomal glutathione S-transferase 1. Various 2-chloropyridine derivatives were metabolized to the corresponding substituted glutathione conjugates via displacement of chlorine atom with glutathione. The reaction was affected by the electron-withdrawing strength and position of the substituents. Molecular orbital calculations on the change in Gibbs free energy between the initial and transition states verified the presence of a Meisenheimer complex and its influence on the reaction rate.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
2-Chloropyridine, 99%