A New Method to synthesize α-Aminoaldehydes
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概要
- 論文の詳細を見る
Benzyloxycarbonyl (Cbz)-amino acid esters were reduced to the corresponding α-aminoaldehydes with diisobutylaluminum hydride. Comparison of specific rotation of the Cbz-aminoalcohols, which were derived from the aldehydes by sodium borohydride reduction, with that of the optically pure material showed that chromatography on a silica gel caused marked racemization in the Cbz-α-aminoaldehyde through keto-enol tautomerism. Cbz-S-Bzl-cysteinal was liable to racemize to a great extent. On the other hand, little racemization occurred in Cbz-N^G-nitroargininal. This fact might be accounted for the characteristic cyclic carbinolamine structure of the argininal derivative. The semicarbazones prepared from the crude Cbz-α-aminoaldehydes could be reproduced to the initial aldehydes without racemization. These semicarbazones might be used as good starting materials in peptide aldehyde synthesis.
- 公益社団法人日本薬学会の論文
- 1975-12-25
著者
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高橋 理恵子
Central Research Laboratories Sankyo Co. Ltd.
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馬場 義彦
Central Research Laboratories, Sankyo Co., Ltd.
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伊藤 章
Central Research Laboratories Sankyo Co. Ltd.
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馬場 義彦
Central Research Laboratories Sankyo Co. Ltd
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