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Bioorganic chemistry à la baguette: Studies on molecular recognition in biological systems using rigid‐rod molecules
Author(s) -
Matile Stefan
Publication year - 2001
Publication title -
the chemical record
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.61
H-Index - 78
eISSN - 1528-0691
pISSN - 1527-8999
DOI - 10.1002/tcr.6
Subject(s) - supramolecular chemistry , chemistry , transmembrane protein , molecule , lipid bilayer , membrane , ion channel , catenation , nanotechnology , stereochemistry , biophysics , chemical physics , crystallography , materials science , receptor , dna , organic chemistry , biochemistry , biology
Initial studies using rigid‐rod molecules or “baguettes” to address bioorganic topics of current scientific concern are reported. It is illustrated how transmembrane oligo( p ‐phenylene)s as representative model rods can be tuned to recognize lipid bilayer membranes either by their thickness or polarization. The construction of otherwise problematic hydrogen‐bonded chains along transmembrane rods yields “proton wires,” which act by a mechanism that is central in bioenergetics but poorly explored by means of synthetic models. Another example focuses on multivalent ligands assembling rigid‐rod cell‐surface receptors into transmembrane dynamic arene arrays. The potassium transport mediated by these ligand‐receptor complexes provides experimental support for the potential biological importances of the controversial cation‐π mechanism. More complex supramolecular architecture is portrayed in the first artificial β‐barrels. It is shown how programmed assembly of toroidal rigid‐rod supramolecules in detergent‐free water permits control of diameter of the chemical nature of their interior. Reversed rigid‐rod β‐barrels are assembled to function as self‐assembled ionophores, ion channel models, and transmembrane nanopores. The potential of future intratoroidal chemistry is exemplified by encapsulation and planarization of β‐carotene in water and the construction of transmembrane B‐DNA at the center of a second‐sphere host‐guest complex à al baguette. © 2001 John Wiley & Sons, Inc. and The Japan Chemical Journal Forum Chem Rec 1:162–172, 2001