Biomimetic Studies Using Artificial Systems. IV. : Biomimetic Peptide Synthesis by Using Multi-Functionalized Crown Ethers as a Novel Enzyme Model. A New Concept in Mimicking of Enzyme-Catalyzed Bond-Forming Reactions
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概要
- 論文の詳細を見る
A novel approach to the mimicking of enzyme-catalyzed bond-forming reactions has been examined using multi-functionalized chiral crown ethers. In addition to the 18-crown-6 moiety as a binding site, the hosts have one thiol and one thio ester with an N-protected α-amino acid or a peptide, and have successfully achieved peptide synthesis in an enzyme-mimetic reaction mode. This new method involves the following three key reactions. (1) Intra-complex thiolysis : the host carries out the rapid intra-complex thiolysis of α-amino acid ester salts to form the dithioester, corresponding to the assembly of two guests by the host. (2) Amide formation : intramolecular aminolysis occurs between the bound guests to form the amide bond. (3) Peptide chain elongation : as the thiol reactive group is regenerated, the above two reactions are repeated to elongate the peptide chain. Formal turnover of the enzyme model has been demonstrated by the synthesis of a tetrapeptide derivative by the repetition of the above processes.
- 公益社団法人日本薬学会の論文
- 1989-04-25
著者
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古賀 憲司
Faculty of Pharmaceutical Sciences, University of Tokyo
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Koga Kenjiro
Department Of Pharmaceutics Faculty Of Pharmaceutical Sciences Hokuriku University
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SASAKI Shigeki
Graduate School of Pharmaceutical Sciences, Kyushu University
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佐々木 茂貴
Faculty Of Pharmaceutical Sciences Kyushu University
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佐々木 茂貴
Faculty Of Pharmaceutical Sciences University Of Tokyo:(present Address)faculty Of Pharmaceutical Sc
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