Self-Assembly of Helical Pores from Nonpolar Dendritic Dipeptides

  • Percec, Virgil (Roy & Dianna Vagelos Laboratories, Department of Chemistry, University of Pennsylvania)
  • Published : 2006.10.13

Abstract

The synthesis of dendritic dipeptides $(4-3,4-3,5)12G2-CH_{2}-Boc-_{L}-Tyr-X-OMe\;where\;X\;=\;Gly,\;_{L}-Val,\;_{L}-Leu,\;_{L}-Ile,\;_{L}-Phe$, and L-Pro will be discussed. Their self-assembly in bulk and in solution and the structural and retrostructural analysis of their periodic assemblies will be compared to that of the previously reported and currently reinvestigated dendritic dipeptide with $X=_{L}-Ala$. All dendritic dipeptides containing as X nonpolar ${\alpha}-amino$ acids self-assemble into helical porous columns. The principles via which the aliphatic and aromatic substituents of X program the structure of the helical pores indicate synthetic pathways to helical pores with bioinspired functions based on artificial nonpolar ${\alpha}-amino$ acids will be discussed.

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