Studies on Hydroxy Amino Acids. IV. Syntheses of Several Peptides Containing Aziridinecarboxylic Acid Derived from the Corresponding Hydroxy Amino Acid Derivatives
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概要
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The β-elimination reaction of the <I>O</I>-tosyl β-hiydroxy amino acid peptide derivative was thoroughly investigated. The <I>N</I>-tosyl-L-serylglycine ester and the <I>N</I>-tosyl-L-threonylglycine ester gave the <I>N</I>-tosyl-L-aziridinecarbonyl-glycine ester and the <I>N</I>-tosyl-3-methyl-L-aziridinecarbonylglycine ester as the resulting products respectively by the elimination reaction. On the other hand, the <I>N</I>-carbobenzoxyglycyl-L-serylglycine ester was not converted into the aziridine peptide derivative; only the dehydroalanine peptide was obtained. However, the <I>N</I>-tosyl-L-phenylalanyl-L-threonylglycine ester and the <I>N</I>-carbobenzoxyglycyl-L-threonylglycine ester were converted into the corresponding aziridine peptide, and the <I>N</I>-tosyl-L-phenylalanyl-3-methyl-L-aziridinecarbonylglycine ester and the <I>N</I>-carbobenzoxyglycyl-3-methyl-L-aziridinecarbonylglycine ester were obtained respectively. It was concluded that the peptides containing threonine were easily converted into the aziridine peptides and not the serine peptides by the β-elimination reaction.
- 公益社団法人 日本化学会の論文
著者
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Iwai Michio
Department Of Chemistry Marine Technical College
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Nakagawa Yasuo
Department Of Applied Physics Faculty Of Engineering Osaka University
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Tsuno Takashi
Department Of Industrial Chemistry College Of Industrial Technology Nihon University
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Nakagawa Yasuo
Department of Chemistry, Faculty of Science, Kwansei Gakuin University
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Nakajima Kiichiro
Department of Chemistry, Faculty of Science, Kwansei Gakuin University
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Okawa Kenji
Department of Chemistry, Faculty of Science, Kwansei Gakuin University
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Iwai Michio
Department of Chemistry, Faculty of Science, Kwansei Gakuin University
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Kawai Haruki
Department of Chemistry, Faculty of Science, Kwansei Gakuin University
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Tsuno Takashi
Department of Chemistry, Faculty of Science, Kwansei Gakuin University
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