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

doi:10.1016/j.inoche.2010.08.001

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^*

^*Corresponding author for this work

School of Advanced Science and Engineering

Research output: Contribution to journal › Article › peer-review

17 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 language	English
Pages (from-to)	1406-1409
Number of pages	4
Journal	Inorganic Chemistry Communications
Volume	13
Issue number	12
DOIs	https://doi.org/10.1016/j.inoche.2010.08.001
Publication status	Published - 2010 Dec

Keywords

Kinetics
L-lactic acid
Mandelic acid
Phenylboronic acid

ASJC Scopus subject areas

Physical and Theoretical Chemistry
Inorganic Chemistry
Materials Chemistry

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10.1016/j.inoche.2010.08.001

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

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.",

keywords = "Kinetics, L-lactic acid, Mandelic acid, Phenylboronic acid",

author = "Eisuke Watanabe and Junko Fujii and Kaori Kojima and Satoshi Iwatsuki and Masahiko Inamo and Takagi, {Hideo D.} and Koji Ishihara",

note = "Funding Information: We wish to express our thanks for financial supports from Waseda University Grant for Special Research Projects (Grant 2009B-123 ). ",

year = "2010",

month = dec,

doi = "10.1016/j.inoche.2010.08.001",

language = "English",

volume = "13",

pages = "1406--1409",

journal = "Inorganic Chemistry Communications",

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T1 - Relative reactivity of phenylboronic acid to phenylboronate ion toward L-lactate and mandelate at physiological pH

AU - Watanabe, Eisuke

AU - Fujii, Junko

AU - Kojima, Kaori

AU - Iwatsuki, Satoshi

AU - Inamo, Masahiko

AU - Takagi, Hideo D.

AU - Ishihara, Koji

N1 - Funding Information: We wish to express our thanks for financial supports from Waseda University Grant for Special Research Projects (Grant 2009B-123 ).

PY - 2010/12

Y1 - 2010/12

N2 - 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.

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.

KW - Kinetics

KW - L-lactic acid

KW - Mandelic acid

KW - Phenylboronic acid

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

Abstract

Keywords

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