The present work will develop several new biomimetic, catalytic systems. The unifying theme is molecular recognition, using a powerful, general class of chiral receptors that we have developed. These hosts are unsurpassed in their ability to bind and orient organic molecules. We now wish to develop these structures into useful catalysts, and we will pursue two different strategies. First, we will use the inherent binding ability of our hosts to electronically bind transition states, and thereby accelerate organic reactions. We have already seen very encouraging preliminary results in this area that suggest new insights into the nature of biological catalysis may be gained. Second, we will modify our hosts to incorporate reactive transition metals as an intrinsic part of the receptor, thereby creating convergent functionality at the binding site. We have targeted several reaction types, and we will be pursuing catalytic rate enhancements and, especially, stereochemical control. Our goal is to develop truly catalytic systems that can accept a broad range of substrates and that enforce substantial stereochemical control. Success in any one of our target systems would constitute a significant advance for bioorganic and synthetic organic chemistry.
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| Dougherty, D A; Stauffer, D A (1990) Acetylcholine binding by a synthetic receptor: implications for biological recognition. Science 250:1558-60 |
