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 glutathione (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-isomer of the bioactive thionitrite, S-nitroso-L-glutathione. The biological activity of both enantiomers of S-nitrosoglutathione has been studied and compared to the activity of the D- and L-isomers of N-acetyl-S-nitrosopenicillamine (SNAP) and S-nitrosocysteine (CysNO).
Cavero
M
M
Chemistry Department, University College London, UK.
Hobbs
A
A
Madge
D
D
Motherwell
W B
WB
Selwood
D
D
Potier
P
P
D000818:Animals; D001011:Aorta; D005978:Glutathione / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000302:isolation & purification / Q000494:pharmacology; D015335:Molecular Probes; D018696:Neuroprotective Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D015538:Nitrosation; D009603:Nitroso Compounds / Q000138:chemical synthesis* / Q000302:isolation & purification / Q000494:pharmacology; D010396:Penicillamine / Q000031:analogs & derivatives / Q000737:chemistry / Q000494:pharmacology; D051381:Rats; D026422:S-Nitrosoglutathione
D015335:Molecular Probes; D018696:Neuroprotective Agents; D009603:Nitroso Compounds; C110881:S-nitro-N-acetylpenicillamine; D026422:S-Nitrosoglutathione; D005978:Glutathione; D010396:Penicillamine