title: Synthesis of boronic acid analogs of L-arginine as alternate substrates or inhibitors of nitric oxide synthase.
abstract: The asymmetric synthesis of an unprotected alpha-amino boronic acid analog of L-arginine 1a (boroarg-OH. 2 HCl) and its N alpha-acetyl derivative 1b (Ac-boroarg-OH. HCl) is described. These compounds were evaluated as substrates and inhibitors of recombinant nitric oxide synthases (NOS). Boroarg-OH 1a selectively inhibited inducible NOS (IC50 = 50 microM) compared to the neuronal isoform (IC50 = 300 microM).
authors.affiliation: UMR CNRS, Université de Rennes 1, France.
authors.forename: C
authors.initials: C
authors.lastname: Lebarbier
authors.forename: F
authors.initials: F
authors.lastname: Carreaux
authors.forename: B
authors.initials: B
authors.lastname: Carboni
authors.forename: J L
authors.initials: JL
authors.lastname: Boucher
mesh_terms: D001120:Arginine / Q000031:analogs & derivatives* / Q000494:pharmacology; D001897:Boronic Acids; D002956:Citrulline / Q000378:metabolism; D004791:Enzyme Inhibitors / Q000138:chemical synthesis* / Q000494:pharmacology; D008956:Models, Chemical; D019001:Nitric Oxide Synthase / Q000037:antagonists & inhibitors* / Q000378:metabolism*; D011994:Recombinant Proteins / Q000037:antagonists & inhibitors / Q000378:metabolism
chemical_list: D001897:Boronic Acids; D004791:Enzyme Inhibitors; D011994:Recombinant Proteins; D002956:Citrulline; D001120:Arginine; D019001:Nitric Oxide Synthase