title: Synthesis of optically pure C alpha-methyl-arginine.
abstract: Optically pure L-(+)-C alpha-methyl-arginine and D-(-)-C alpha-methyl-arginine were synthesized. Experimental results indicated that DL-C alpha-methyl-arginine methyl ester could be resolved by trypsin, but workup posed a technical difficulty. Chemical resolution at the stage of DL-C alpha-methyl-ornithine, followed by selective guanidination using N,N'-di-Cbz-S-methylisothiourea and hydrogenolysis provided a effective and practical method for the synthesis of optically pure C alpha-methyl-arginine.
authors.affiliation: Department of Biochemistry and Molecular Biology, Indiana University School of Medicine, Indianapolis.
authors.forename: Z
authors.initials: Z
authors.lastname: Tian
authors.forename: P
authors.initials: P
authors.lastname: Edwards
authors.forename: R W
authors.initials: RW
authors.lastname: Roeske
mesh_terms: D001120:Arginine / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D013237:Stereoisomerism
chemical_list: C012427:2-methylarginine; D001120:Arginine