Synthesis and biological evaluation of enantiopure thionitrites: The solid-phase synthesis and nitrosation of -glutathione as a molecular probe

The -isomer of the naturally-occurring tripeptide glutathione (γ- -Glu- -Cys-Gly, -GSH) has been synthesised using the Fmoc solid phase peptide synthesis strategy. The -GSH obtained has been nitrosated to give the -isomer of the bioactive thionitrite, S-nitroso- -glutathione. The biological activity of both enantiomers of S-nitrosoglutathione has been studied and compared to the activity of the - and -isomers of N-acetyl-S-nitrosopenicillamine (SNAP) and S-nitrosocysteine (CysNO).