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 in | Journal of antibiotics Vol. 29; no. 3; pp. 221 - 226 |
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| Main Authors | , , |
| Format | Journal Article |
| Language | English |
| Published |
Japan
JAPAN ANTIBIOTICS RESEARCH ASSOCIATION
1976
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| Subjects | |
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| 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}-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. |
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| AbstractList | 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. 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. |
| Author | YARMCHUK, L. LEACH, M. MAEHR, H. |
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| References | 6) HOPPE, D.: α-Metalated isocyanides in organic synthesis. Angew. Chem. Internat. Ed. 13: 789-804, 1974 8) TURK, J.; G.T. PANSE & G. R. MARSHALL: Studies with α-methylamino acids. Resolution and amino protection. J. Org. Chem. 40: 953-955, 1975 1) MAEHR, H.; YARMCHUK, L., D. L. PRUESS, M. KELLETT, N. J. PALLERONI, B. LA T. PROSSER & T. C. DEMNYL: Antimetabolites produced by microorganisms. XIV. 2-Methyl-L-arginine, a new amino acid with antibiotic properties. J. Antibiotics 29: 213-220, 1976 2) ELLINGTON, J. J. & I. L. HONIGBERG: The synthesis of 2-methylproline and 2-methylornithine. J. Org. Chem. 39: 104-106, 1974 3) ABDEL-MONEM, M. M.; N. E. NEWTON & C. E. WEEKS: Inhibitors of polyamine biosynthesis. 1. α-Methyl-(±)-ornithine, an inhibitor of ornithine decarboxylase. J. Med. Chem. 17: 447-451, 1974 4) WEINGES, K. & B. STEMMLE: Die asymmetrische Strecker-Synthese von aliphatischen α-Methyl-α-aminosauren. Chem. Ber. 106: 2291-2297, 1973 7) HOPPE, D.: Kettenverlangerte und α-verzweigte α-Aminosäuren durch Alkylierung metallierter N-[Bis(alkylthio)methylen]-α-aminosäureester. Angew. Chem. 87: 450-451, 1975. 10) BRETSCHNEIDER, H. & N. KARPITSCHKA: Zur Stellungsisomersierung beim Umsatz von Halohydrinen mit NaN3 und Darstellung des 1-Phenyl-1-amino-2,3-propandiols. Monatsh. Chem. 84: 1044-1052, 1953 11) Worthington Enzyme Manual: Worthington Biochemical Corporation, Freehold, New Jersey, 07728, U.S.A. 1972 5) MEYERS, A. I.; G. KNAUS & K. KAMATA: Synthesis via 2-oxazolines. IV. An asymmetric synthesis of 2-methylalkanoic acids from a chiral oxazoline. J. Amer. Chem. Soc. 96: 268-270, 1974 9) KURTZ, A. C.: Use of copper (II) ion in masking α-amino groups of amino acids. J. Biol. Chem. 180: 1253-1267, 1949 |
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| SubjectTerms | Arginine - analogs & derivatives Arginine - chemical synthesis Chemical Phenomena Chemistry Imidazoles Ornithine - analogs & derivatives Ornithine - chemical synthesis |
| Subtitle | SYNTHESIS OF 2-METHYL-L-ARGININE, 2-METHYL-L-ORNITHINE AND THEIR ENANTIOMERS |
| Title | ANTIMETABOLITES PRODUCED BY MICROORGANISMS. XV |
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