We have used hydration free energies computed using quantum chemical methods as predictors of the reactivity of a variety of biologically active compounds. Our initial studies involved using the hydration energies of purine analogs as predictors of their proficiency as substrates for deaminase enzymes (e.g. ADAR2) studied by the Beal group at UC Davis. Subsequent studies have involved using the hydration energies of ketoamides present in drugs as predictors of whether or not they will form covalent adducts with their biological targets.
Pokharel, S.; Jayalath, P.; Maydanovych, O.; Goodman, R.; Wang, S. C.; Tantillo, D. J.; Beal, P. A. J. Am. Chem. Soc. 2009, 131, 11882-11891: "Matching Active Site and Substrate Structures for an RNA Editing Reaction"
Wang, S. C.; Beal, P. A.; Tantillo, D. J. J. Comput. Chem. 2010, 31, 721-725: "Covalent Hydration Energies for Purine Analogs by Quantum Chemical Methods"
Wedler, H. B.; Palazzo, T. A.; Pemberton, R. P.; Hamann, C. S.; Kurth, M. J.; Tantillo, D. J. Bioorg. Med. Chem. Lett., 2015, 25, 4153-4157: "Predicting Hydration Propensities of Biologically Relevant alpha-Ketoamides"
Laconsay, C. J.; Rho, T. C.; Tantillo, D. J. J. Org. Chem. 2022, 87, 3378-3388: "The Role of Through-Bond Stereoelectronic Effects in the Reactivity of 3-Azabicyclo[3.3.1]nonanes"
Henry B. Wedler, Christian S. Hamann, and Dean J. Tantillo: "TheTheoretical Hydration Energues of Biologically Relevant alpha-Ketoamides." Poster presented by Hoby Wedler at the SYLICCO.09 Symposium, Davis, CA, July 23, 2009.
Henry B. Wedler, Christian S. Hamann and Dean J. Tantillo: "Theoretical Hydration Energies of Biologically Relevant alpha-Keto Amides." Poster presented by Hoby Wedler at the 239th ACS National Meeting, San Francisco, CA, March 21-25, 2010; paper ORGN 715.
Henry B. Wedler, Christian S. Hamann and Dean J. Tantillo: "Theoretical Hydration Energies of Biologically Relevant alpha-Keto Amides." Poster presented by Hoby Wedler at the R. Bryan Miller Symposium, UC Davis, Davis, CA, April 8-9, 2010.
Henry Wedler (sponsored by Dean J. Tantillo): "Theoretical Hydration Energies of Biologically Relevant alpha-Keto Amides." Lecture presented by Hoby Wedler at the 21st Annual Conference on Undergraduate Research, Scholarship and Creative Activities, University of California, Davis, CA, May 1, 2010.
Henry Wedler, Christian S. Hamann and Dean J. Tantillo: "Theoretical Hydration Energies of Biologically Relevant alpha-Keto Amides." Lecture presented by Hoby Wedler at the 22nd Annual Northern California ACS Undergraduate Research Symposium, Sacramento, CA, May 8, 2010.
Henry Wedler, Christian S. Hamann and Dean J. Tantillo: "Theoretical Hydration Energies of Biologically Relevant alpha-Keto Amides." Lecture presented by Hoby Wedler at the 2010 Richard Larock Undergraduate Research Conference, UC Davis, Davis, CA, May 22, 2010.
Henry Wedler, Christian S. Hamann and Dean J. Tantillo: "Theoretical Hydration Energies of Biologically Relevant alpha-Keto Amides." Poster presented by Hoby Wedler at the 33rd Reaction Mechanisms Conference, University of Massachusetts, Amherst, MA, June 23-26, 2010.
Henry Wedler, Christian S. Hamann and Dean J. Tantillo: "Theoretical Hydration Energies of Biologically Relevant alpha-Keto Amides." Poster presented by Hoby Wedler at the 9th MECURY Conference, Hamilton College, Clinton, NY, August 1-3, 2010.
