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We calculated (AMBER* forcefield GB\/SA CHCl3solvation model Macromodel version 7.1 Schrodinger Inc. USA 2000) the minimum energy conformations of the both theendoandexocycloadducts from all of the possible combinations of these six building blocks. Of the possible cycloadducts only one combination endo\u20103from the reaction between1with2 had the desired open template structure required for replication and warranted further investigation."},{"key":"e_1_2_2_70_2","unstructured":"The ratio ofendo\u20103andexo\u20103did not change upon heating the reaction mixtures to 60\u2009\u00b0C; additionally heatingendo\u20103andexo\u20103withN\u2010phenylmaleimide did not result in any crossover products being formed. These results suggest that no thermodynamic equilibration betweenendoandexocycloadducts occurs within the temperature range and on the timescale of our investigations."},{"key":"e_1_2_2_71_2","unstructured":"Maximum rates (velocities) of reaction were calculated by determining the largest value of the first derivative of the function that describes the concentration\u2013time profile for each reaction; for bimolecular reactions this metric is equivalent to the initial rate; for autocatalytic reactions this represents the point of inflection of the sigmoidal curve."},{"key":"e_1_2_2_72_2","unstructured":"On the basis of the observed signal\u2010to\u2010noise ratios in the1H NMR spectra (500 MHz) of the reaction mixtures we estimate that our limit of detection forexo\u20103is 100 \u03bcM. This analysis places a lower limit of 250:1 on theendo\/exoselectivity generated by the recognition\u2010mediated reaction."},{"key":"e_1_2_2_73_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200301739"},{"key":"e_1_2_2_73_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200301739"},{"key":"e_1_2_2_74_2","doi-asserted-by":"publisher","DOI":"10.1021\/ar020076v"},{"key":"e_1_2_2_75_2","unstructured":"Raising the temperature will diminish theKavalue for the product duplex by increasing the magnitude of theT\u0394Sterm in the free energy of binding. We recognize that the change in temperature will also affect the stability of other complexes in solution; however as the behavior of the system is sensitive to the product duplexKavalue we wished to use these means to explore this effect qualitatively. A detailed analysis of the effect of temperature on this system will be reported elsewhere. 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