Collect. Czech. Chem. Commun. 1987, 52, 425-430

Reactivity of 2-furylethylenes with nucleophilic groups and its biological significance

Michal Rosenberg, Štefan Baláž, Ernest Šturdík and Anton Kuchár

Department of Biochemical Technology, Slovak Institute of Technology, 812 37 Bratislava


The paper describes addition-nucleophilic reactions of 1-(5-R1-2-furyl)-2-R2-R3-ethylenes with SH (thioglycolic acid), NH2 (glycine) and OH (phenol) nucleophiles, and with hydroxyl ions in aqueous media. The determined rate constants, of second order (dm3 mol-1 s-1), show that in the physiological conditions the preferential reaction will be that with thiols. The amino acid composition of proteins modified with 1-(5-nitro-2-furyl)-2-nitro-2-methoxycarbonylethylene has revealed that the only group affected was the SH group of cysteine. This finding points out the significance of addition-nucleophilic SH-interactions of 2-furylethylenes with the protein macromolecules and accounts for the high cytotoxicity of these compounds.