Abstract:
: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.
journal_name
ACS Med Chem Lettjournal_title
ACS medicinal chemistry lettersauthors
Tomsho JW,Pal A,Hall DG,Benkovic SJdoi
10.1021/ml200215jsubject
Has Abstractpub_date
2011-10-19 00:00:00pages
48-52issue
1issn
1948-5875journal_volume
3pub_type
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