Journal
ACS MEDICINAL CHEMISTRY LETTERS
Volume 3, Issue 1, Pages 48-52Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ml200215j
Keywords
Benzoxaborole; oxaborole; benzoboroxole; benzoxaborin; boronic acid; diol binding; Hammett relationship; pK(a) prediction
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Funding
- Natural Sciences and Engineering Research Council of Canada
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In this work, we present an investigation into the physical properties of a unique class of aromatic boronic acids, the benzoxaboroles. Using spectrophotometric methods, the ionization constants of a family of substituted benzoxaboroles are determined. Heterocyclic ring modifications are examined to determine their effects on the ionization of the boronic acid moiety. It is also shown that the substituent effects about the aromatic ring follow a Hammett relationship with the compounds' measured pK(a) values. Finally, these substituent effects are also shown to extend to the sugar binding properties of these compounds under physiologically relevant conditions. Combined, these data will inform medicinal chemists wishing to tailor the ionization and/or ability of this class of compound to bind diol-containing biomolecules.
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