Tuning the Handedness: Role of Chiral Component in Peptide-Appended Bolaamphiphile-Based Coassembled Hydrogels

Abstract

Chirality is the intrinsic property of a molecule that can be tuned by the change in chirality of a molecule or by the addition of a chiral component as an external stimulus. An l-leucine-based dipeptide-appended succinic acid-based bolaamphiphile coassembled with d-tartaric acid to form supramolecular right-handed nanostructured hydrogel, whereas l-tartaric acid coassembled to form supramolecular left-handed nanostructured hydrogel. Scanning electron microscopy and transmission electron microscopy experiments revealed the right- and left-handed helical nanofibers that are responsible for the formation of supramolecular nanostructured hydrogels. The synergistic chiral effect of l-leucine in peptide bolaamphiphile and d/l-tartaric acid plays a significant role in bicomponent gelation with helical nanofibers. The first two amino acids attached to both sides of succinic acid moiety act as a tuning button for supramolecular chirality of amino acids/peptides attached with succinic acid-based bolaamphiphiles. The second amino acid plays the role of modulating supramolecular chirality if the first two amino acids act neutrally to the chirality of bolaamphiphiles, which was confirmed by circular dichroism spectroscopy. Copyright © 2019 American Chemical Society.