Design and synthesis of isomeric molecules for bioorganic and combinatorial chemistry studies.

摘要

Non-bonded interactions are important forces in determining the structure of any molecular ensemble. Here we describe our efforts to understand the nature of CH-π interaction and the hydrophobic effect. In addition, the application of non-bonded interaction forces such as CH-π and π-π interaction into bioorganic and organic systems is reported. An ethanoanthracene-based torsion balance was designed and synthesized to estimate the Coulombic contribution to the CH-π interaction. Due to the rigidity of the ethanoanthracene unit, this new torsion balance could not achieve effective CH-π attractive force. To test the idea of the hydrophobic effect on the binding of the ligand to protein, α-methylbiotin was synthesized and its binding to avidin was measured by microcalorimetry. The binding of both isomers of α-methylbiotin was less exothermic than biotin itself. Utilizing the fact that E -stilbene isomer is generally less soluble than the corresponding Z-isomer, we discovered two important stilbene derivatives. These compounds, which we call “precipitons”, were used to develop a new method of product isolation. Three organic reactions were run with these “precipitons” to show the practical utility of the concept of product isolation by precipitation.