Functionalization of crown ethers: An approach to the enzyme model for peptide synthesis

Kenji Koga, Shigeki Sasaki

Research output: Contribution to journalArticle

18 Citations (Scopus)

Abstract

Chiral crown ethers having two thiol groups were designed and synthesized as an approach to the enzyme model for peptide synthesis. The strategy of the present method consists of four fundamental steps as shown in Scheme II, i.e., (1) mono-ester formation by intracomplex thiolysis followed by protection of the amino group (6 to 10), (2) di-ester formation by intracomplex thiolysis (10 to 13), (3) peptide bond formation by intramolecular aminolysis with regeneration of one free thiol group (13 to 15), and (4) elongation of peptide chain by repeating the above steps (2) and (3). Synthesis of tri- and tetra-peptide derivatives by this method is descirbed.

Original languageEnglish
Pages (from-to)539-543
Number of pages5
JournalPure and Applied Chemistry
Volume60
Issue number4
DOIs
Publication statusPublished - Jan 1 1988

All Science Journal Classification (ASJC) codes

  • Chemistry(all)
  • Chemical Engineering(all)

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