Insight into hydrolytic reaction of N-acetylated l-histidylglycine dipeptide with novel mechlorethamine platinum(ii) complex. NMR and DFT study of the hydrolytic reaction

Abstract

The reaction of K 2PtCl 4 with the alkylating agent mechlorethamine hydrochloride, at a molar ratio of 1:2, results in the formation of 2-chloro-N-(2-chloroethyl)-N-methylethylammonium-tetrachloridoplatinate(II) complex. The hydrolytic activity of the novel Pt(ii) complex was tested in the reaction with N-acetylated l-histidylglycine dipeptide at a molar ratio 1:1. It was shown that the hydrolytic reaction, performed at 60 °C in acidic medium, leads to the regioselective cleavage of the amide bond involving the carboxylic group of histidine. Density functional theory was used to explore the structures of the proposed participants in the hydrolytic reaction. © 2011 The Royal Society of Chemistry.