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Article
Tuning Nanopore Formation of Oligocholate Macrocycles by Carboxylic Acid Dimerization in Lipid Membranes
Journal of Organic Chemistry
  • Lakmini Sandachaya Widanapathirana, Iowa State University
  • Yan Zhao, Iowa State University
Document Type
Article
Disciplines
Publication Version
Published Version
Publication Date
4-1-2013
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
Citation Information
Lakmini 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/