PRODUCTION OF HELICAL BILAYER-MEMBRANES FROM L-GLUTAMIC ACID-DERIVATIVES WITH BIS(DODECYLAMIDE) GROUPS AND THEIR SPECIFIC OPTICAL-ACTIVITY

Double-chain alkyl amphiphiles with polypeptide head-groups can form helical superstructures composed of uni-lamellar bilayer membranes in dilute aqueous solutions. In this study, various amphiphiles with an L-glutamic acid moiety was prepared as a model compound to study the structure of molecular aggregates. As a result, it was confirmed that the amphiphiles with three or more amide bondings per molecule could form helical aggregates and their mechanism of metamorphosis was similar to those of polypeptide amphiphiles. In addition, the helical aggregates had two phase transitions and showed chiral reversibility between negative to positive states around the first phase transition. We conclude that the plural amide bondings near the chiral carbon of amphiphiles contribute to the production of helical aggregates and specific chirality change. © 1990, The Chemical Society of Japan. All rights reserved.