Multi-functionalized chiral crown ethers as enzyme models for the synthesis of peptides. Multiple chiral recognition in the enzyme model

Shigeki Sasaki, Kenji Koga

研究成果: ジャーナルへの寄稿学術誌査読

15 被引用数 (Scopus)

抄録

A novel approach to the enzyme model for the synthesis of peptides has been established by using multi-functionalized chiral crown ethers as hosts. The new strategy consists of three key steps as follows. (1) Guest assembly: the host having one free thiol and one thioester with N-protected α-amino acid or peptide proceeds via rapid intra-complex thiolysis of α-amino acid ester salts to form the dithioester, and assembles two guests. (2) Amide formation: the 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. In the present paper, we describe the multiple chiral recognition that could be achieved by the chiral crown ether in both the intra-complex thiolysis and the intramolecular aminolysis. For explanation of the chiral recognition, we propose a likely structure for the intermediate of the aminolysis.

本文言語英語
ページ(範囲)267-276
ページ数10
ジャーナルJournal of Inclusion Phenomena and Molecular Recognition in Chemistry
7
2
DOI
出版ステータス出版済み - 4月 1 1989
外部発表はい

!!!All Science Journal Classification (ASJC) codes

  • 食品科学
  • 化学 (全般)
  • 凝縮系物理学

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