Nanotube Formation by Hydrophobic Dipeptides

• Published in: Chemistry : a European journal 2001-12, Vol.7 (23), p.5153-5159
• Main Author: Görbitz, Carl Henrik
• Format: Article
• Language: English
• Subjects: Crystallography, X-Ray; Dimerization; Dipeptides - chemistry; Ion Channels - chemical synthesis; Ion Channels - chemistry; Models, Molecular; Molecular Structure; nanostructures; Nanotechnology - methods; peptides; self-assembly; Solubility; supramolecular structure
• ISSN: 0947-6539; 1521-3765
• DOI: 10.1002/1521-3765(20011203)7:23<5153::AID-CHEM5153>3.0.CO;2-N

A wide range of applications has been suggested for peptide‐based nanotubes, which first attracted considerable interest as model systems for membrane channels and pores. The intriguing and unprecedented observation of nanotube formation by supramolecular self‐assembly of the four dipeptides L‐Leu‐L‐Leu, L‐Leu‐L‐Phe, L‐Phe‐L‐Leu and L‐Phe‐L‐Phe is described here. These simple compounds crystallize with hydrogen‐bonded head‐to‐tail chains in the shape of helices with four to six peptide molecules per turn. The resulting structures have chiral hydrophilic channels with a van der Waals' diameter up to 10 Å. The intriguing and unprecedented observation of the formation of nanotubes in the crystal state by the supramolecular self‐assembly of four Leu‐ and Phe‐based dipeptides is reported. The channels (see scheme) have chiral hydrophilic inner surfaces and diameters up to 10 Å. These supramolecular assemblies can serve as models for transmembrane structures, and may also be exploited as chiral receptors.