News & Notices

Home Page

Pure Appl. Chem. Vol. 72, No. 3, pp. 365-372, 2000

Designer cyclopeptides for self-assembled tubular structures*

Darshan Ranganathan**, C. Lakshmi, V. Haridas, and M. Gopikumar

Discovery Laboratory, Indian Institute of Chemical Technology, Hyderabad 500 007, India

Abstract: A simple design strategy for a facile and direct entry into hydrogen-bonded peptide nanotubes is delineated with polymethylene-bridged cystine-based macrocycles. The key feature of the design is the placement of a pair of self-complementary hydrogen-bonding (NH�CO or NH�CO�NH) groups at almost opposite poles of the ring. A large variety of cyclobisamides and bisureas prepared in a single step by direct condensation of commercially available 1,w-alkane dicarbonyl dichloride or diisocyanate with either cystine diOMe or its extended bispeptide were examined by X-ray crystallography and shown to possess an inherent property of self-assembling into hydrogen-bonded, open-ended, hollow tubular structures. The totally hydrophobic interior of the cyclobisamide tubes creates a micro environment capable of solubilizing highly lipophilic substances in water. The cyclic bisurea tubes are demonstrated to act as excellent receptors for selective binding to 1,w-alkane dicarboxylates. The scope of the design is extended to the creation of tubular structures by stacking of rings through aromatic p -p interactions.

*Lecture presented at the 5^th International IUPAC Symposium on Bioorganic Chemistry (ISBOC-5), Pune, India, 30 January - 4 February, 2000.
**Corresponding author

Back to Contents for access to full text