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.
All Science Journal Classification (ASJC) codes
- Chemical Engineering(all)