Nature 366, 324 - 327 (25 December 1993); doi:10.1038/366324a0

Self-assembling organic nanotubes based on a cyclic peptide architecture

M. Reza Ghadiri, Juan R. Granja, Ronald A. Milligan, Duncan E. McRee & Nina Khazanovich

Departments of Chemistry, Molecular Biology, and Cell Biology, The Scripps Research Institute, La Jolla, California 92307, USA

HOLLOW tubular structures of molecular dimensions may offer a variety of applications in chemistry, biochemistry and materials science. Concentric carbon nanotubes^1,2 have attracted a great deal of attention, while the three-dimensional tubular pore structures of molecular sieves have long been exploited industrially^3–8. Nanoscale tubes based on organic materials have also been reported previously^9–13. Here we report the design, synthesis and characterization of a new class of organic nanotubes based on rationally designed cyclic polypeptides. When protonated, these compounds crystallize into tubular structures hundreds of nanometres long, with internal diameters of 7–8 Å. Support for the proposed tubular structures is provided by electron microscopy, electron diffraction, Fourier-transform infrared spectroscopy and molecular modelling. These tubes are open-ended, with uniform shape and internal diameter. We anticipate that they may have possible applications in inclusion chemistry, catalysis, molecular electronics and molecular separation technology.

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