N-Acyl Homoserine Lactones (AHLs) are molecules found in gram negative bacteria used for a chemical communication process known as quorum sensing. Modulation of quorum sensing is controlled by hydrolysis of the lactone component of the molecule. A critical n to π* orbital interaction of the butyrolactone has been hypothesized to attenuate hydrolysis. In our study, para-substitution of the benzoyl-AHL derivative was explored to understand how electron donating and withdrawing groups affect hydrolysis. Substituted benzoyl groups were chosen to specifically study the potential influence of inductive and resonance effects on the n to π* interaction. The n to π* orbital interaction of the butyrolactone leading to hydrolysis was affected by these substitutions. HPLC was used to examine the variation in rates of hydrolysis to calculate relative rates and assess how electron donating and withdrawing groups affect hydrolysis.

Manipulation of n to π* orbital interactions in the hydrolysis of para-substituted N-acyl homoserine lactones

249th National Meeting (2015)

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