Synthesis of optically pure C alpha-methyl-arginine.
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.
Tian
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Department of Biochemistry and Molecular Biology, Indiana University School of Medicine, Indianapolis.
Edwards
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P
Roeske
R W
RW
D001120:Arginine / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D013237:Stereoisomerism
C012427:2-methylarginine; D001120:Arginine