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Wedler, Henry B.; Palazzo, Teresa A.; Pemberton, Ryan P.; Hamann, Christian S.; Kurth, Mark J.; Tantillo, Dean J.
Bioorganic & medicinal chemistry letters, 10/2015, Letnik: 25, Številka: 19Journal Article
Display omitted Quantum chemical calculations coupled to experiments were used to predict covalent hydration propensities of biologically relevant α-ketoamides. Experimentally determined hydration equilibrium constants for related ketones and aldehydes were compared to computationally determined values to develop a method for predicting hydration equilibrium constants. This method was used on six newly synthesized α-ketoamides to experimentally verify computational predictions. A correlation between calculation and experiment was observed and applied to models of several pertinent APIs. Our results indicate that the keto form is favored for practically all α-ketoamides in biological environs.
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