Campus Units

Chemistry

Document Type

Article

Publication Version

Published Version

Publication Date

4-2013

Journal or Book Title

Journal of Organic Chemistry

Volume

78

Issue

9

First Page

4610

Last Page

4614

DOI

10.1021/jo400455x

Abstract

Oligocholate macrocycles self-assemble into transmembrane nanopores by the associative interactions of water molecules inside the amphiphilic macrocycles. Macrocycles functionalized with a terephthalic acid “side chain” displayed significantly higher transport activity for glucose across lipid bilayers than the corresponding methyl ester derivative. Changing the 1,4-substitution of the dicarboxylic acid to 1,3-substitution lowered the activity. Combining the hydrophobic interactions and the hydrogen-bond-based carboxylic acid dimerization was an effective strategy to tune the structure and activity of self-assembled nanopores in lipid membranes.

Comments

Reprinted (adapted) with permission from Journal of Organic Chemistry 78 (2013): 4610, doi:10.1021/jo400455x. Copyright 2013 American Chemical Society.

Copyright Owner

American Chemical Society

Language

en

File Format

application/pdf

Included in

Chemistry Commons

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