Organic nanotubes from diaminopyridine derived lipids

COLL 534

George John, Rensselaer Nanotechnology Center and Department of Chemical and Biological Engineering, Rensselaer Poytechnic Institute, 101 Ricketts, 110 8th Street, Troy, NY 12180 and Jonathan S. Dordick, Department of Chemical and Biological Engineering, Rensselaer Polytechnic Institute, 110 8th St, Troy, NY 12180.
Recent fundamental research has revealed the possibility to rationally form supramolecular aggregates from biomolecules such as lipids, polypeptides or proteins. These self-assembled structures range in size from several nanometers to hundreds of microns in well defined morphologies including ribbons, helices, and tubes. We have recently demonstrated that similar morphology with the identical size dimensions can be obtained by an effort to combine the philosophies of green chemistry and supramolecular chemistry. We found that lipid nanotubes characterized by nanometer size dimensions of 10-15 nm inner diameter, 40-50 outer diameter, and axial ratios of more than 1000 can be self-assembled from amphiphilic glycolipids. Based on this chemistry, we have designed and synthesized new glycolipids having additional functional arms to bind biomolecules to mimic biological events in nanoscale dimensions. A two step synthetic strategy afforded novel glycolipids from diaminopyridine. The self-assembly of the new amphiphiles in water resulted lipid nanotubes via helical coiled nanofibers- of size dimensions 10-20 nm inner diameter and 40-80 nm outer diameter, revealed by optical and scanning microscopic techniques. Further evidence to the proposed structures are provided by X-ray diffraction and spectroscopic studies.