New Methods and Reagents in Organic Synthesis. 69. A New Synthesis of α-Amino Acid and Peptide Amides of Aromatic Amines Using a Modified Curtius Reaction with Diphenyl Phosphorazidate(Organic,Chemical)

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概要

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• As a basic study on the efficient synthesis of chromogenic and fluorogenic peptidase substrates, we investigated possible general methods for the synthesis of α-amino acid and peptide amides of aromatic amines. Preparation of Boc-L-Leu-pNA (1) as a model compound was attempted by (1) the coupling of Boc-L-Leu-OH with p-nitroaniline, (2) the reaction of Boc-L-Leu-OH with p-nitrophenyl isocyanate, and (3) the reaction of Boc-L-Leu-OH with the product formed from p-nitrobenzoic acid through the modified Curtius reaction with diphenyl phosphorazidate ((C_6H_5O)_2P(O)N_3) in a one-pot process. The third method was found to be a general and efficient method for the preparation of α-amino acid amides of aromatic amines. Application of this method to the preparation of a peptidase substrate, Bz-L-Ile-L-Glu(Ome)-Gly-L-Arg-pNA (2), has also been successfully achieved.

• 公益社団法人日本薬学会の論文
• 1987-07-25

著者

• 塩入 孝之

  名市大・薬

• 浜田 康正

  Faculty of Pharmaceutical Sciences, Nagoya City University

• 塩入 孝之

  Faculty of Pharmaceutical Sciences, Nagoya City University

• 塩入 孝之

  名城大院・総合学術

• 塩入 孝之

  Faculty Of Pharmaceutical Sciences Nagoya City University

• 塩入 孝之

  名古屋市大・薬

• 村田 充男

  Research Center, Taisho Pharmaceutical Co., Ltd.,

• 村田 充男

  Faculty of Pharmaceutical Sciences, Nagoya City University

• 村田 充男

  Research Center Taisho Pharmaceutical Co. Ltd.

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