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N5-Hydroxy-2-methylornithine and N5-hydroxy-2-methylarginine were synthesized. 2-Amino-5-hydroxy-2-methylpentanoic acid was prepared from 5-hydroxy-2-pentanone and converted to N-(tetrahydro-3-methyl-2-oxo-2H-pyran-3-yl) acetamide which was treated with hydrogen bromide affording 2-(acetylamino)-5-bromo-2-methylpentanoic acid. This acid was esterified with methanol and used to alkylate anti-benzaldoxime yielding methyl 2-(acetylamino)-2-methyl-5-[(phenylmethylene)amino]-pentanoate N5-oxide which, upon hydrolysis, yielded N5-hydroxy-2-methylornithine, and, upon aminolysis and short acid-treatment, gave N2-acetyl-N5-hydroxy-2-methylornithinamide. Carbamimidoylation and hydrolysis of the latter compound furnished N5-hydroxy-2-methylarginine.

Antimetabolites produced by microorganisms. XVI. Synthesis of N5-hydroxy-2-methylarginine and N5-hydroxy-2-methylornithine.