Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
Chemical Conversion of L-α, ω-Diamino Acids to L-ω-Carbamoyl-α-amino Acids by Ruthenium Tetroxide Oxidation
SHIGEYUKI YOSHIFUJIKEN-ICHI TANAKAYOSHIHIRO NITTA
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1987 Volume 35 Issue 7 Pages 2994-3001

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Abstract

Ruthenium tetroxide oxidation of N, C-protected derivatives of L-2, 4-diaminobutyric acid, L-ornithine and L-lysine was carried out under two-phase conditions and the corresponding imides, formed through the oxidation of the methylene adjacent to the ω-amino group, were obtained in good yields. Removal of the protecting groups from the products gave L-asparagine, L-glutamine and L-2-aminoadipic acid 6-amide, respectively. Thus, the first chemical conversion of L-α, ω-diamino acids into the corresponding L-ω-carbamoyl-α-amino acids without racemization has been established. L-2-Aminoadipic acid 6-amide was further converted to L-2-aminoadipic acid by acid hydrolysis. This represents a convenient method for the synthesis of L-2-aminoadipic acid starting from L-lysine.

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© The Pharmaceutical Society of Japan
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