Predicting hydration propensities of biologically relevant α-ketoamides

Henry B. Wedler, Teresa A. Palazzo, Ryan P. Pemberton, Christian S. Hamann, Mark J. Kurth, Dean J. Tantillo

Research output: Contribution to journalArticlepeer-review

1 Scopus citations

Abstract

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.

Original languageEnglish (US)
Pages (from-to)4153-4157
Number of pages5
JournalBioorganic and Medicinal Chemistry Letters
Volume25
Issue number19
DOIs
StatePublished - Oct 1 2015

Keywords

  • Density functional theory
  • Hydration propensity
  • Predictive methods
  • Theory versus experiment
  • α-Ketoamide

ASJC Scopus subject areas

  • Biochemistry
  • Clinical Biochemistry
  • Molecular Biology
  • Molecular Medicine
  • Organic Chemistry
  • Drug Discovery
  • Pharmaceutical Science

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