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

Eisuke Watanabe, Junko Fujii, Kaori Kojima, Satoshi Iwatsuki, Masahiko Inamo, Hideo D. Takagi, Koji Ishihara

Research output: Contribution to journalArticle

15 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)1406-1409
Number of pages4
JournalInorganic Chemistry Communications
Volume13
Issue number12
DOIs
Publication statusPublished - 2010 Dec 1

    Fingerprint

Keywords

  • Kinetics
  • L-lactic acid
  • Mandelic acid
  • Phenylboronic acid

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Inorganic Chemistry
  • Materials Chemistry

Cite this