Reactivity and mechanism of the reactions of 4-methylbenzoquinone with amino acid residues in β-lactoglobulin: A kinetic and product investigation

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Standard

Reactivity and mechanism of the reactions of 4-methylbenzoquinone with amino acid residues in β-lactoglobulin : A kinetic and product investigation. / Liu, Jingyuan; Engholm-Keller, Kasper; Poojary, Mahesha M.; Bevilacqua, Marta; Andersen, Mogens L.; Lund, Marianne N.

In: Food Chemistry, Vol. 434, 137473, 2024.

Research output: Contribution to journal › Journal article › Research › peer-review

Harvard

Liu, J, Engholm-Keller, K, Poojary, MM, Bevilacqua, M, Andersen, ML & Lund, MN 2024, 'Reactivity and mechanism of the reactions of 4-methylbenzoquinone with amino acid residues in β-lactoglobulin: A kinetic and product investigation', Food Chemistry, vol. 434, 137473. https://doi.org/10.1016/j.foodchem.2023.137473

APA

Liu, J., Engholm-Keller, K., Poojary, M. M., Bevilacqua, M., Andersen, M. L., & Lund, M. N. (2024). Reactivity and mechanism of the reactions of 4-methylbenzoquinone with amino acid residues in β-lactoglobulin: A kinetic and product investigation. Food Chemistry, 434, [137473]. https://doi.org/10.1016/j.foodchem.2023.137473

Vancouver

Liu J, Engholm-Keller K, Poojary MM, Bevilacqua M, Andersen ML, Lund MN. Reactivity and mechanism of the reactions of 4-methylbenzoquinone with amino acid residues in β-lactoglobulin: A kinetic and product investigation. Food Chemistry. 2024;434. 137473. https://doi.org/10.1016/j.foodchem.2023.137473

Author

Liu, Jingyuan ; Engholm-Keller, Kasper ; Poojary, Mahesha M. ; Bevilacqua, Marta ; Andersen, Mogens L. ; Lund, Marianne N. / Reactivity and mechanism of the reactions of 4-methylbenzoquinone with amino acid residues in β-lactoglobulin : A kinetic and product investigation. In: Food Chemistry. 2024 ; Vol. 434.

Bibtex

@article{f15961c036994f05a3c2fede928f1366,
title = "Reactivity and mechanism of the reactions of 4-methylbenzoquinone with amino acid residues in β-lactoglobulin: A kinetic and product investigation",
abstract = "Quinones, produced by the oxidation of phenolic compounds, covalently bind to nucleophilic groups on amino acids or proteins. In this study, the reactions of 4-methylbenzoquinone (4MBQ) with β-lactoglobulin (β-LG) and amino acids at neutral pH were investigated. LC-MS analysis revealed that Cys121 was likely the most modified residue in β-LG. Identification of reaction products by LC-MS/MS showed that Michael addition occurred in all reactions with amino acids tested. The formation of Schiff base and a di-adduct was found in His and Trp samples. Apparent second-order rate constants (k2) were determined at 25 °C and pH 7.0 by stopped-flow spectrophotometry. The rate of reactions decreased in the order: β-LG > His > Trp > Arg > Nα-acetyl His > Nα-acetyl Arg > Nα-acetyl Trp. The rate constants correlated with the pKa values of the amino acids, showing that the amount of unprotonated amine is the major factor determining the reactivity.",
keywords = "4-methylcatechol, Kinetics, Michael addition, Polyphenol-protein binding, Protein modification, β-lactoglobulin",
author = "Jingyuan Liu and Kasper Engholm-Keller and Poojary, {Mahesha M.} and Marta Bevilacqua and Andersen, {Mogens L.} and Lund, {Marianne N.}",
note = "Publisher Copyright: {\textcopyright} 2023 The Author(s)",
year = "2024",
doi = "10.1016/j.foodchem.2023.137473",
language = "English",
volume = "434",
journal = "Food Chemistry",
issn = "0308-8146",
publisher = "Elsevier",

}

RIS

TY - JOUR

T1 - Reactivity and mechanism of the reactions of 4-methylbenzoquinone with amino acid residues in β-lactoglobulin

T2 - A kinetic and product investigation

AU - Liu, Jingyuan

AU - Engholm-Keller, Kasper

AU - Poojary, Mahesha M.

AU - Bevilacqua, Marta

AU - Andersen, Mogens L.

AU - Lund, Marianne N.

N1 - Publisher Copyright: © 2023 The Author(s)

PY - 2024

Y1 - 2024

N2 - Quinones, produced by the oxidation of phenolic compounds, covalently bind to nucleophilic groups on amino acids or proteins. In this study, the reactions of 4-methylbenzoquinone (4MBQ) with β-lactoglobulin (β-LG) and amino acids at neutral pH were investigated. LC-MS analysis revealed that Cys121 was likely the most modified residue in β-LG. Identification of reaction products by LC-MS/MS showed that Michael addition occurred in all reactions with amino acids tested. The formation of Schiff base and a di-adduct was found in His and Trp samples. Apparent second-order rate constants (k2) were determined at 25 °C and pH 7.0 by stopped-flow spectrophotometry. The rate of reactions decreased in the order: β-LG > His > Trp > Arg > Nα-acetyl His > Nα-acetyl Arg > Nα-acetyl Trp. The rate constants correlated with the pKa values of the amino acids, showing that the amount of unprotonated amine is the major factor determining the reactivity.

AB - Quinones, produced by the oxidation of phenolic compounds, covalently bind to nucleophilic groups on amino acids or proteins. In this study, the reactions of 4-methylbenzoquinone (4MBQ) with β-lactoglobulin (β-LG) and amino acids at neutral pH were investigated. LC-MS analysis revealed that Cys121 was likely the most modified residue in β-LG. Identification of reaction products by LC-MS/MS showed that Michael addition occurred in all reactions with amino acids tested. The formation of Schiff base and a di-adduct was found in His and Trp samples. Apparent second-order rate constants (k2) were determined at 25 °C and pH 7.0 by stopped-flow spectrophotometry. The rate of reactions decreased in the order: β-LG > His > Trp > Arg > Nα-acetyl His > Nα-acetyl Arg > Nα-acetyl Trp. The rate constants correlated with the pKa values of the amino acids, showing that the amount of unprotonated amine is the major factor determining the reactivity.

KW - 4-methylcatechol

KW - Kinetics

KW - Michael addition

KW - Polyphenol-protein binding

KW - Protein modification

KW - β-lactoglobulin

U2 - 10.1016/j.foodchem.2023.137473

DO - 10.1016/j.foodchem.2023.137473

M3 - Journal article

C2 - 37738814

AN - SCOPUS:85171880901

VL - 434

JO - Food Chemistry

JF - Food Chemistry

SN - 0308-8146

M1 - 137473

ER -

ID: 372525204