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Issue 13, 2019
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Homochiral nanotubes from heterochiral lipid mixtures: a shorter alkyl chain dominated chiral self-assembly

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Abstract

It is an important topic to achieve homochirality both at a molecular and supramolecular level. While it has long been regarded that “majority rule” guides the homochiral self-assembly from an enantiomer mixture, it still remains a big challenge to manipulate the global homochirality in a complex system containing chiral species that are not enantiomers. Here, we demonstrate a new example wherein homochiral nanotubes self-assembled from a mixture of heterochiral lipids that deviated from the “majority rule”. We have found that when two heterochiral lipids with mirror headgroups but a 2-methylene discrepancy in alkyl chain length are mixed, homochiral nanotubes are always formed regardless of their mixing ratio. Remarkably, the helicity of the nanotube is exclusively controlled by the molecular chirality of the lipids with shorter alkyl chains, i.e., the chiral self-assembly was dominated by the lipid with the shorter alkyl chain. MD simulation reveals that the match of both the alkyl chain length and hydrogen-bonding between two kinds of lipids plays an important role in the assembly. This work provides a new insight into the supramolecular chirality of complex systems containing multi chiral species.

Graphical abstract: Homochiral nanotubes from heterochiral lipid mixtures: a shorter alkyl chain dominated chiral self-assembly

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Publication details

The article was received on 15 Jan 2019, accepted on 19 Feb 2019 and first published on 20 Feb 2019


Article type: Edge Article
DOI: 10.1039/C9SC00215D
Chem. Sci., 2019,10, 3873-3880
  • Open access: Creative Commons BY license
    All publication charges for this article have been paid for by the Royal Society of Chemistry

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    Homochiral nanotubes from heterochiral lipid mixtures: a shorter alkyl chain dominated chiral self-assembly

    X. Zhu, Y. Jiang‡, D. Yang, L. Zhang, Y. Li and M. Liu, Chem. Sci., 2019, 10, 3873
    DOI: 10.1039/C9SC00215D

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