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

    14 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

    Fingerprint

    lactates
    Lactic Acid
    reactivity
    Ions
    acids
    Acids
    lactic acid
    Lactic acid
    ions
    Boronic Acids
    Ligands
    Kinetics
    ligands
    kinetics
    Rate constants
    benzeneboronic acid
    Sensors
    aqueous solutions
    sensors
    mandelic acid

    Keywords

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

    ASJC Scopus subject areas

    • Inorganic Chemistry
    • Physical and Theoretical Chemistry
    • Materials Chemistry

    Cite this

    Relative reactivity of phenylboronic acid to phenylboronate ion toward L-lactate and mandelate at physiological pH. / Watanabe, Eisuke; Fujii, Junko; Kojima, Kaori; Iwatsuki, Satoshi; Inamo, Masahiko; Takagi, Hideo D.; Ishihara, Koji.

    In: Inorganic Chemistry Communications, Vol. 13, No. 12, 12.2010, p. 1406-1409.

    Research output: Contribution to journalArticle

    Watanabe, Eisuke ; Fujii, Junko ; Kojima, Kaori ; Iwatsuki, Satoshi ; Inamo, Masahiko ; Takagi, Hideo D. ; Ishihara, Koji. / Relative reactivity of phenylboronic acid to phenylboronate ion toward L-lactate and mandelate at physiological pH. In: Inorganic Chemistry Communications. 2010 ; Vol. 13, No. 12. pp. 1406-1409.
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    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.",
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    AU - Iwatsuki, Satoshi

    AU - Inamo, Masahiko

    AU - Takagi, Hideo D.

    AU - Ishihara, Koji

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    AB - 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.

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