A helical, aromatic, peptide nanotube

Org Lett. 2006 Dec 21;8(26):6091-4. doi: 10.1021/ol062600u.

Abstract

[Structure: see text] The self-assembly in the crystal state of the terminally protected, linear dipeptide Boc-(S,S)c3diPhe-(R,R)c3diPhe-NHiPr (1) through intermolecular hydrogen bonds leads to the formation of a supramolecular helix of large diameter (18 A), internally decorated with phenyl rings. As a result, a hollow helical channel large enough to accommodate guest molecules is observed. This supramolecular structure differs from previous examples of peptide nanotubes. Compound 1 incorporates a highly restricted cyclopropane phenylalanine analogue (c3diPhe) with remarkable conformational properties.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Crystallization
  • Models, Molecular
  • Nanotubes, Peptide*
  • X-Ray Diffraction

Substances

  • Nanotubes, Peptide