Tuning Nanopore Formation of Oligocholate Macrocycles by Carboxylic Acid Dimerization in Lipid MembranesJournal of Organic Chemistry
Publication VersionPublished Version
AbstractOligocholate 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.
Copyright OwnerAmerican Chemical Society
Citation InformationLakmini Sandachaya Widanapathirana and Yan Zhao. "Tuning Nanopore Formation of Oligocholate Macrocycles by Carboxylic Acid Dimerization in Lipid Membranes" Journal of Organic Chemistry Vol. 78 Iss. 9 (2013) p. 4610 - 4614
Available at: http://works.bepress.com/yan_zhao/2/