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Bioorganic Chemistry à la Baguette: Studies on Molecular Recognition in Biological Systems Using Rigid-Rod Molecules

Published in Chemical Record. 2001, vol. 1, no. 2, p. 162-172
Abstract 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-pi mechanism. More complex supramolecular architecture is portrayed in the first artificial beta-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 beta-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 beta-carotene in water and the construction of transmembrane B-DNA at the center of a second-sphere host-guest complex à al baguette.
Keywords Host-guest complexesIon channelsMolecular recognitionOligomersPeptidomimetics
PMID: 11893065
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MATILE, Stefan. Bioorganic Chemistry à la Baguette: Studies on Molecular Recognition in Biological Systems Using Rigid-Rod Molecules. In: Chemical Record, 2001, vol. 1, n° 2, p. 162-172. https://archive-ouverte.unige.ch/unige:7912

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Deposited on : 2010-06-21

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