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微生物产生的抗代谢物。XV. 2-甲基-L-精氨酸、2-甲基-L-鸟氨酸及其对映体的合成。

Antimetabolites produced by microorganisms. XV Synthesis of 2-methyl-L-arginine, 2-methyl-L-ornithine and their enantiomers.

作者信息

Maehr H, Yarmchuk L, Leach M

出版信息

J Antibiot (Tokyo). 1976 Mar;29(3):221-6. doi: 10.7164/antibiotics.29.221.

DOI:10.7164/antibiotics.29.221
PMID:1262253
Abstract

5-(3-Azidopropyl)-5-methyl-2, 4-imidazolidinedione was prepared either from 5-(3-chloropropyl)-5-methyl-2,4-imidazolidinedione or 5-methyl-5-(3-[(4-methylphenyl)sulfonyloxy]-propyl)-5-methyl-2, 4-imidazolidinedione and hydrogenolyzed to the corresponding amine which, after carbamimidoylation, afforded 2-methyl-DL-arginine upon acid hydrolysis. Racemic 2-methylarginine was converted enzymically to a mixture of 2-methyl-D-arginine and 2-methyl-L-ornithine. 2-Methyl-L-arginine was reconstructed from 2-methyl-L-ornithine via its Cu(II) chelate with O-methyl-isourea and 2-methyl-D-ornithine was obtained by alkaline hydrolysis of 2-methyl-D-arginine.

摘要

5-(3-叠氮基丙基)-5-甲基-2,4-咪唑啉二酮可由5-(3-氯丙基)-5-甲基-2,4-咪唑啉二酮或5-甲基-5-(3-[(4-甲基苯基)磺酰氧基]丙基)-2,4-咪唑啉二酮制备,并进行氢解得到相应的胺,该胺经氨基甲脒化后,经酸水解得到2-甲基-DL-精氨酸。外消旋2-甲基精氨酸经酶转化为2-甲基-D-精氨酸和2-甲基-L-鸟氨酸的混合物。2-甲基-L-精氨酸由2-甲基-L-鸟氨酸通过其与O-甲基异脲的Cu(II)螯合物重构得到,2-甲基-D-精氨酸经碱性水解得到2-甲基-D-鸟氨酸。

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Antimetabolites produced by microorganisms. XV Synthesis of 2-methyl-L-arginine, 2-methyl-L-ornithine and their enantiomers.微生物产生的抗代谢物。XV. 2-甲基-L-精氨酸、2-甲基-L-鸟氨酸及其对映体的合成。
J Antibiot (Tokyo). 1976 Mar;29(3):221-6. doi: 10.7164/antibiotics.29.221.
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