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Oxidation of amino acids by peracetic acid: Reaction kinetics, pathways and theoretical calculations

Peracetic acid (PAA) is a sanitizer with increasing use in food, medical and water treatment industries. Amino acids are important components in targeted foods for PAA treatment and ubiquitous in natural waterbodies and wastewater effluents as the primary form of dissolved organic nitrogen. To bette...

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Autores principales: Du, Penghui, Liu, Wen, Cao, Hongbin, Zhao, He, Huang, Ching-Hua
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Elsevier 2018
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6646862/
https://www.ncbi.nlm.nih.gov/pubmed/31367703
http://dx.doi.org/10.1016/j.wroa.2018.09.002
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author Du, Penghui
Liu, Wen
Cao, Hongbin
Zhao, He
Huang, Ching-Hua
author_facet Du, Penghui
Liu, Wen
Cao, Hongbin
Zhao, He
Huang, Ching-Hua
author_sort Du, Penghui
collection PubMed
description Peracetic acid (PAA) is a sanitizer with increasing use in food, medical and water treatment industries. Amino acids are important components in targeted foods for PAA treatment and ubiquitous in natural waterbodies and wastewater effluents as the primary form of dissolved organic nitrogen. To better understand the possible reactions, this work investigated the reaction kinetics and transformation pathways of selected amino acids towards PAA. Experimental results demonstrated that most amino acids showed sluggish reactivity to PAA except cysteine (CYS), methionine (MET), and histidine (HIS). CYS showed the highest reactivity with a very rapid reaction rate. Reactions of MET and HIS with PAA followed second-order kinetics with rate constants of 4.6 ± 0.2, and 1.8 ± 0.1 M(−1)⋅s(−1) at pH 7, respectively. The reactions were faster at pH 5 and 7 than at pH 9 due to PAA speciation. Low concentrations of H(2)O(2) coexistent with PAA contributed little to the oxidation of amino acids. The primary oxidation products of amino acids with PAA were [O] addition compounds on the reactive sites at thiol, thioether and imidazole groups. Theoretical calculations were applied to predict the reactivity and regioselectivity of PAA electrophilic attacks on amino acids and improved mechanistic understanding. As an oxidative disinfectant, the reaction of PAA with organics to form byproducts is inevitable; however, this study shows that PAA exhibits lower and more selective reactivity towards biomolecules such as amino acids than other common disinfectants, causing less concern of toxic disinfection byproducts. This attribute may allow greater stability and more targeted actions of PAA in various applications.
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spelling pubmed-66468622019-07-31 Oxidation of amino acids by peracetic acid: Reaction kinetics, pathways and theoretical calculations Du, Penghui Liu, Wen Cao, Hongbin Zhao, He Huang, Ching-Hua Water Res X Full Paper Peracetic acid (PAA) is a sanitizer with increasing use in food, medical and water treatment industries. Amino acids are important components in targeted foods for PAA treatment and ubiquitous in natural waterbodies and wastewater effluents as the primary form of dissolved organic nitrogen. To better understand the possible reactions, this work investigated the reaction kinetics and transformation pathways of selected amino acids towards PAA. Experimental results demonstrated that most amino acids showed sluggish reactivity to PAA except cysteine (CYS), methionine (MET), and histidine (HIS). CYS showed the highest reactivity with a very rapid reaction rate. Reactions of MET and HIS with PAA followed second-order kinetics with rate constants of 4.6 ± 0.2, and 1.8 ± 0.1 M(−1)⋅s(−1) at pH 7, respectively. The reactions were faster at pH 5 and 7 than at pH 9 due to PAA speciation. Low concentrations of H(2)O(2) coexistent with PAA contributed little to the oxidation of amino acids. The primary oxidation products of amino acids with PAA were [O] addition compounds on the reactive sites at thiol, thioether and imidazole groups. Theoretical calculations were applied to predict the reactivity and regioselectivity of PAA electrophilic attacks on amino acids and improved mechanistic understanding. As an oxidative disinfectant, the reaction of PAA with organics to form byproducts is inevitable; however, this study shows that PAA exhibits lower and more selective reactivity towards biomolecules such as amino acids than other common disinfectants, causing less concern of toxic disinfection byproducts. This attribute may allow greater stability and more targeted actions of PAA in various applications. Elsevier 2018-10-05 /pmc/articles/PMC6646862/ /pubmed/31367703 http://dx.doi.org/10.1016/j.wroa.2018.09.002 Text en © 2018 Published by Elsevier Ltd. http://creativecommons.org/licenses/by-nc-nd/4.0/ This is an open access article under the CC BY-NC-ND license (http://creativecommons.org/licenses/by-nc-nd/4.0/).
spellingShingle Full Paper
Du, Penghui
Liu, Wen
Cao, Hongbin
Zhao, He
Huang, Ching-Hua
Oxidation of amino acids by peracetic acid: Reaction kinetics, pathways and theoretical calculations
title Oxidation of amino acids by peracetic acid: Reaction kinetics, pathways and theoretical calculations
title_full Oxidation of amino acids by peracetic acid: Reaction kinetics, pathways and theoretical calculations
title_fullStr Oxidation of amino acids by peracetic acid: Reaction kinetics, pathways and theoretical calculations
title_full_unstemmed Oxidation of amino acids by peracetic acid: Reaction kinetics, pathways and theoretical calculations
title_short Oxidation of amino acids by peracetic acid: Reaction kinetics, pathways and theoretical calculations
title_sort oxidation of amino acids by peracetic acid: reaction kinetics, pathways and theoretical calculations
topic Full Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6646862/
https://www.ncbi.nlm.nih.gov/pubmed/31367703
http://dx.doi.org/10.1016/j.wroa.2018.09.002
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