Synthesis of threo-3-methylcysteine from threonine.
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概要
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<I>threo</I>-3-Methyl-D-cysteine as a moiety of β-methyllanthionine in the peptide antibiotic nisin was synthesized stereospecifically. The reaction of (2<I>R</I>,3<I>R</I>)-3-methyl-2-aziridinecarboxylic acid derivative prepared from D-threonine with thiobenzoic acid gave the β-mercapto α-amino acid derivative of the same configuration as the starting material. A stereochemistry of the product was retained as a result of double inversion mechanism through the reactions. Thus, we could prepare <I>threo</I>-3-methyl-D-cysteine, <I>i.e.</I>, (2<I>S</I>,3<I>S</I>)-2-amino-3-mercaptobutanoic acid which is required for the synthetic study of nisin.
- 公益社団法人 日本化学会の論文
著者
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Shiba Tetsuo
Department Of Chemistry Faculty Of Science Osaka University
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Wakamiya Tateaki
Department Of Chemistry Faculty Of Science Osaka University
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Shimbo Kuniaki
Department of Chemistry, Faculty of Science, Osaka University
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Nakajima Kiichiro
Department of Chemistry, Faculty of Science, Kwansei Gakuin University
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Neya Masahiro
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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