ANTIMETABOLITES PRODUCED BY MICROORGANISMS. XV SYNTHESIS OF 2-METHYL-L-ARGININE, 2-METHYL-L-ORNITHINE AND THEIR ENANTIOMERS

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}-2, 4-imidazolidinedione and hydrogenolyzed to the corresponding amine which, after carbamimidoylation, afforded 2-met...

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Published inJournal of antibiotics Vol. 29; no. 3; pp. 221 - 226
Main Authors MAEHR, H., YARMCHUK, L., LEACH, M.
Format Journal Article
LanguageEnglish
Published Japan JAPAN ANTIBIOTICS RESEARCH ASSOCIATION 1976
Subjects
Arginine - analogs & derivatives
Arginine - chemical synthesis
Chemical Phenomena
Chemistry
Imidazoles
Ornithine - analogs & derivatives
Ornithine - chemical synthesis
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Summary: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}-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.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
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ISSN:0021-8820
1881-1469
DOI:10.7164/antibiotics.29.221