NG-hydroxyguanidines from primary amines.
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.
Martin
Nathaniel I
NI
Department of Chemistry, University of California-Berkeley, 204 Lewis Hall, Berkeley, CA 94720, USA. nimartin@berkeley.edu
Woodward
Joshua J
JJ
Marletta
Michael A
MA
D000588:Amines / Q000737:chemistry*; D006146:Guanidines / Q000138:chemical synthesis*; D015394:Molecular Structure
D000588:Amines; D006146:Guanidines