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

The D-isomer of the naturally-occurring tripeptide glulathione (gamma-L-Glu -L-Cys-Gly, L-GSH) has been synthesised using the Fmoc solid phase peptide synthesis strategy. The D-GSH obtained has been nitrosated to give the D-is omer of the bioactive thionitrite, S-nitroso-L-glutathione. The biological activity of both enantiomers of S-nitrosoglutathione has been studied and c ompared to the activity of the D- and L-isomers of N-acetyl-S-nitrosopenici llamine (SNAP) and S-nitrosocysteine (CysNO). (C) 2000 Elsevier Science Ltd . All rights reserved.