Earlier studies of our research group on the enzyme factor Xa yielded two oxazole containing inhibitors.[1]  The 11-fold difference in binding affinity was surprising since X-ray co-crystal analysis showed almost identical binding modes (Figure: PDB codes 2Y5G and 2Y5H). Noncovalent interactions between p�systems are important in molecular recognition and routinely used in rational drug design.[2]  Amide groups are exposed in many enzyme active sites.  We used quantum chemical calculations to systematically study the stacking of aromatic molecules on planar amide fragments.  [1]  L. M. Salonen, M. C. Holland, P. S. J. Kaib, W. Haap, J. Benz, J. L. Mary, O. Kuster, W. B. Schweizer, D. W. Banner, F. Diederich, Chem. Eur. J. 2012 , 18, 213�222. [2]  L. M. Salonen, M. Ellermann, F. Diederich, Ang. Chem. Int. Ed. 2011 , 50, 4808�4842.

Systematic investigation of amide stacking

245th National Meeting (2013)

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