title: NG-hydroxyguanidines from primary amines.
abstract: A concise and general method for the preparation of N(G)-hydroxyguanidines from primary amines is reported. Using available and readily prepared materials, primary amines are converted to protected N(G)-hydroxyguanidines in a one-pot procedure followed by deprotection under nonreducing conditions. The method has been successfully applied to a number of examples including a high-yielding preparation of N(G)-hydroxy-L-arginine, the intermediate in the enzymatic conversion of L-arginine to nitric oxide and L-citrulline by nitric oxide synthase.
authors.affiliation: Department of Chemistry, University of California-Berkeley, 204 Lewis Hall, Berkeley, CA 94720, USA. nimartin@berkeley.edu
authors.forename: Nathaniel I
authors.initials: NI
authors.lastname: Martin
authors.forename: Joshua J
authors.initials: JJ
authors.lastname: Woodward
authors.forename: Michael A
authors.initials: MA
authors.lastname: Marletta
mesh_terms: D000588:Amines / Q000737:chemistry*; D006146:Guanidines / Q000138:chemical synthesis*; D015394:Molecular Structure
chemical_list: D000588:Amines; D006146:Guanidines