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Design, Synthesis, and Structural Analysis of d,l-Mixed Polypyrrolinones. 2. Macrocyclic Hexapyrrolinones

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journal contribution
posted on 2010-07-02, 00:00 authored by Amos B. Smith, III, Hui Xiong, Adam K. Charnley, Meinrad Brenner, Eugen F. Mesaros, Craig S. Kenesky, Luigi Di Costanzo, David W. Christianson, Ralph Hirschmann
The design, synthesis, and structural analysis of two macrocyclic d,l-alternating hexapyrrolinones have been achieved. These cyclic peptide mimics adopt a flat, hexagonal conformation, stabilized by intramolecular hydrogen bonding between adjacent pyrrolinone rings. Extensive NMR studies and X-ray analysis reveal, respectively, that the macrocyclic hexapyrrolinones aggregate in solution and in the solid state form staggered stacked nanotube-like assemblies.