Chemical Conversion of L-α,ω-Diamino Acids to L-ω-Carbamoyl-α-amino Acids by Ruthenium Tetroxide Oxidation(Organic,Chemical)

• 吉藤 茂行

  School of Pharmacy, Hokuriku University

• 田中 憲一

  School of Pharmacy, Hokuriku University

• 新田 義博

  School of Pharmacy, Hokuriku University

抄録

Ruthenium tetroxide oxidation of N, C-protected derivatives of L-2,4-diarainobutyric 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-ammo group, were obtained in good yields. Removal of the protecting groups from the products gave L-asparagine, L-glutamine and L-2-arninoadipic acid 6-amide, respectively. Thus, the first chemical conversion of L-α,ω-diamino acids into the corresponding L-ω-carbamoyl-a-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.

収録刊行物

• Chem. Pharm. Bull.

  Chem. Pharm. Bull. 35 2994-3001, 1987

  公益社団法人日本薬学会

キーワード

• oxidation
• ruthenium tetroxide oxidation
• L-α-amino acid synthesis
• N-protecting group
• ruthenium tetroxide
• L-α,ω-diamino acid
• L-ω-carbamoyl-α-amino acid
• L-2-aminoadipicacid

詳細情報

• CRID: 1572543027185714688
• NII論文ID: 110006281351
• NII書誌ID: AA00602100
• ISSN: 00092363
• 本文言語コード: en
• データソース種別:
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