微生物产生的抗代谢物XVI. N5-羟基-2-甲基精氨酸和N5-羟基-2-甲基鸟氨酸的合成

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

作者信息

Maehr H, Leach M

出版信息

J Antibiot (Tokyo). 1978 Mar;31(3):165-9. doi: 10.7164/antibiotics.31.165.

DOI:10.7164/antibiotics.31.165

Abstract

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.

摘要

合成了N5-羟基-2-甲基鸟氨酸和N5-羟基-2-甲基精氨酸。由5-羟基-2-戊酮制备2-氨基-5-羟基-2-甲基戊酸，并将其转化为N-(四氢-3-甲基-2-氧代-2H-吡喃-3-基)乙酰胺，该酰胺用溴化氢处理得到2-(乙酰氨基)-5-溴-2-甲基戊酸。该酸用甲醇酯化，用于烷基化反苯甲醛肟，得到N5-氧化物甲基2-(乙酰氨基)-2-甲基-5-[(苯基亚甲基)氨基]戊酸酯，水解后得到N5-羟基-2-甲基鸟氨酸，经氨解和短时间酸处理后得到N2-乙酰基-N5-羟基-2-甲基鸟氨酰胺。后者化合物的氨基甲脒化和水解得到N5-羟基-2-甲基精氨酸。

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