Adventures in molecular recognition. The ins and outs of templating*
Jeremy K. M. Sanders
University Chemical Laboratory, Lensfield Road, Cambridge
CB2 1EW, UK
Abstract: Two different approaches are described for the creation
of supramolecular systems potentially capable of recognition and catalysis.
Using the design approach, we have been able to accelerate and influence
two different DielsAlder reactions within the cavities of porphyrin
dimers and trimers; this is templating from the outside inwards. The
selection approach is a synthetic chemical attempt to capture some of
the key evolutionary features of biological systems: dynamic combinatorial
chemistry is used to create equilibrating mixtures of potential receptors,
and then a template is used to select and amplify the desired system.
Five potential reactions for such dynamic chemistry are discussed: base-catalyzed
transesterification, hydrazone exchange, disulfide exchange, alkene
metathesis, and Pd-catalyzed allyl exchange, and preliminary templating
results (inside outwards) are presented.
*Plenary lecture presented at the 15th
International Conference on Physical Organic Chemistry (ICPOC 15), Göteborg,
Sweden, 8 –13 July 2000. Other presentations are published in this
issue, pp. 2219 –2358.
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