Relative reactivity of phenylboronic acid to phenylboronate ion toward L-lactate and mandelate at physiological pH

doi:10.1016/j.inoche.2010.08.001

Inorganic Chemistry Communications

Volume 13, Issue 12, December 2010, Pages 1406-1409

https://doi.org/10.1016/j.inoche.2010.08.001 Get rights and content

Abstract

Kinetic studies were performed on the reactions of phenylboronic acid with L-lactic acid and mandelic acid in acidic aqueous and alkaline solutions in order to specify reactive species in these reactions. It was confirmed that the diprotonated ligand (H₂L: L-lactic acid or mandelic acid) is less reactive than the monoprotonated ligand (HL⁻: L-lactate ion or mandelate ion), which made possible direct determination of the rate constants of phenylboronic acid (PhB(OH)₂) and its conjugate base, phenylboronate ion (PhB(OH)₃⁻). It was found that PhB(OH)₂ is more reactive than PhB(OH)₃⁻. On the basis of kinetic results, it was concluded that the most reactive species are PhB(OH)₂ and HL⁻ at physiological pH 7.4, so the reaction in the boronic acid-based sensor for L-lactate mainly would occur between these species.

Graphical Abstract

Detailed kinetic studies were performed on the reactions of phenylboronic acid with L-lactic acid and mandelic acid in acidic and alkaline solutions, and reactive species were fully specified.

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Acknowledgement

We wish to express our thanks for financial supports from Waseda University Grant for Special Research Projects (Grant 2009B-123).

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