139461-37-3Relevant articles and documents
An improved synthesis of N(G)-allyl-(L)-arginine
Bernatowicz,Matsueda
, p. 657 - 661 (1993)
A novel, more efficient and practical synthesis of the title compound, recently reported as a potent inhibitor of nitric oxide synthase is described. Reaction of (L)-ornithine with 1H-pyrazole-N-allyl-1-carboxamidine allowed facile isolation of the title product in 70% yield.
NG-Allyl- and NG-Cyclopropyl-L-arginine: Two Novel Inhibitors of Macrophage Nitric Oxide Synthase
Olken, Norman M.,Marletta, Michael A.
, p. 1137 - 1144 (2007/10/02)
NG-Methyl-L-arginine has recently been shown to inactivate the inducible murine macrophage nitric oxide (.NO) synthase (Olken, N.M.; Rusche, K.M.; Richards, M.K.; Marletta, M.A.Biochem.Biophys.Res.Commun. 1991, 177, 828-833).NG-Allyl-L-arginine and NG-cyclopropyl-L-arginine were synthesized as potential mechanism-based enzyme inhibitors to exploit the chemistry presumed to occur at the active site.NG-Cyclopropyl-L-arginine was found to be a potent reversible inhibitor with a Ki = 7.7 μM.NG-Allyl-L-arginine was found to be both a potent reversible (Ki = 2.1 μM) and irreversible inhibitor of the enzyme.The irreversible inhibition demonstrated pseudo-first-order inactivation kinetics with kinact = 0.026 min-1 and Ki = 3.4 μM.Stereospecific protection of the inactivation was afforded by L-arginine, and saturability of the inactivation rate was observed.Our studies indicate that both reversible and irreversible inhibition of the inducible .NO synthase can be achieved with relatively simple modifications of the substrate L-arginine.
