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Article
Efficient Construction of Oligocholate Foldamers via “Click” Chemistry and Their Tolerance of Structural Heterogeneity
Organic Letters
  • Xingang Pan, Iowa State University
  • Yan Zhao, Iowa State University
Document Type
Article
Disciplines
Publication Version
Published Version
Publication Date
1-1-2009
DOI
10.1021/ol802364c
Abstract
The 1,3-dipolar cycloaddition between an alkynyl-terminated cholate trimer and an azido-functionalized cholate hexamer readily afforded the nonamer and dodecamer derivatives, whereas amide coupling employed in previous oligocholate synthesis failed beyond the octamer. Unlike typical oligocholate foldamers with exclusively head-to-tail arrangement of the repeat units, the newly synthesized “clicked” oligocholates contained head-to-head arrangement and flexible tethers in the sequence. Despite large structural perturbations, the clicked oligocholates folded similarly as the parent foldamers, demonstrating the robustness of the solvophobically driven folding mechanism.
Comments

Reprinted (adapted) with permission from Organic Letters 11 (2009): 69, doi:10.1021/ol802364c. Copyright 2009 American Chemical Society.

Copyright Owner
American Chemical Society
Language
en
File Format
application/pdf
Citation Information
Xingang Pan and Yan Zhao. "Efficient Construction of Oligocholate Foldamers via “Click” Chemistry and Their Tolerance of Structural Heterogeneity" Organic Letters Vol. 11 Iss. 1 (2009) p. 69 - 72
Available at: http://works.bepress.com/yan_zhao/4/