Efficient construction of oligocholate foldamers via "click" chemistry and their tolerance of structural heterogeneity.
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.
Pan
Xingang
X
Department of Chemistry, Iowa State University, Ames, Iowa 50011-3111, USA.
Zhao
Yan
Y
D000480:Alkynes / Q000737:chemistry; D001386:Azides / Q000737:chemistry; D002240:Carbohydrate Sequence; D020355:Cholates / Q000138:chemical synthesis* / Q000737:chemistry; D003500:Cyclization; D000432:Methanol / Q000737:chemistry; D008968:Molecular Conformation; D008969:Molecular Sequence Data; D013237:Stereoisomerism
D000480:Alkynes; D001386:Azides; D020355:Cholates; D000432:Methanol