Design, Synthesis, and Structural Analysis of d,l-Mixed Polypyrrolinones. 1. From Nonpeptide Peptidomimetics to Nanotubes

To expand the potential conformational space available to the polypyrroline structural motif, an open chain, d,l-alternating hexapyrrolinone was designed and synthesized. Structural studies, including solution NMR and X-ray crystallographic analysis, revealed that the hexapyrrolinone adopts a turn c...

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Veröffentlicht in:Organic letters 2010-07, Vol.12 (13), p.2990-2993
Hauptverfasser: Smith, III, Amos B, Wang, Wenyong, Charnley, Adam K, Carroll, Patrick J, Kenesky, Craig S, Hirschmann, Ralph
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Sprache:eng
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Zusammenfassung:To expand the potential conformational space available to the polypyrroline structural motif, an open chain, d,l-alternating hexapyrrolinone was designed and synthesized. Structural studies, including solution NMR and X-ray crystallographic analysis, revealed that the hexapyrrolinone adopts a turn conformation both in solution and in the solid state, with aggregation in solution and a nanotube-like quaternary structure in the crystal.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol101007n