TY - JOUR
T1 - Functionalization of crown ethers
T2 - An approach to the enzyme model for peptide synthesis
AU - Koga, Kenji
AU - Sasaki, Shigeki
N1 - Funding Information:
The authors express their sincere appreciation to their coworkers, Dr. Motoji Kawasaki, Mr. Mitsuhiko Shionoya, Elr. Hisaaki Chaki, and Mr. Kenji Ohta for their enthusiastic contribution. Partial financial support from the Science and Technology Agency, Japan, is gratefully acknowledged.
PY - 1988/1/1
Y1 - 1988/1/1
N2 - 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.
AB - 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.
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U2 - 10.1351/pac198860040539
DO - 10.1351/pac198860040539
M3 - Article
AN - SCOPUS:37949052406
SN - 0033-4545
VL - 60
SP - 539
EP - 543
JO - Pure and Applied Chemistry
JF - Pure and Applied Chemistry
IS - 4
ER -