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