Dipeptide Nanotubes Containing Unnatural Fluorine-Substituted β(2,3)-Diarylamino Acid and L-Alanine as Candidates for Biomedical Applications

Org Lett. 2015 Sep 18;17(18):4468-71. doi: 10.1021/acs.orglett.5b02132. Epub 2015 Sep 3.

Abstract

The synthesis and the structural characterization of dipeptides composed of unnatural fluorine-substituted β(2,3)-diarylamino acid and L-alanine are reported. Depending on the stereochemistry of the β amino acid, these dipeptides are able to self-assemble into proteolytic stable nanotubes. These architectures were able to enter the cell and locate in the cytoplasmic/perinuclear region and represent interesting candidates for biomedical applications.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alanine / chemistry*
  • Amino Acids / chemistry*
  • Crystallography, X-Ray
  • Dipeptides / chemical synthesis*
  • Dipeptides / chemistry
  • Dipeptides / pharmacology
  • Fluorine / chemistry*
  • Molecular Conformation
  • Molecular Structure
  • Nanotubes
  • Nuclear Magnetic Resonance, Biomolecular
  • Stereoisomerism

Substances

  • Amino Acids
  • Dipeptides
  • Fluorine
  • Alanine