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Kinetic study of the 2-methyl-3-methoxy-4-phenylbutanoic acid produced by oxidation of microcystin in aqueous solutions
Wu, Xingqiang1,2; Xiao, Bangding1,2; Gong, Yan1,2; Wang, Zhi1,2; Chen, Xiaoguo3; Li, Renhui1; Xiao, BD, Chinese Acad Sci, Inst Hydrobiol, Wuhan 430072, Hubei, Peoples R China
2008-10-01
Source PublicationENVIRONMENTAL TOXICOLOGY AND CHEMISTRY
ISSN0730-7268
Volume27Issue:10Pages:2019-2026
AbstractMicrocystins (MCs) are a family of related cyclic hepatotoxic heptapeptides, of which more than 70 types have been identified. The chemically unique nature of the C20 beta-amino acid, (2S, 3S, 8S, 9S)-3-amino-9-methoxy-2,6,8-trimethyl-10-phenyldeca4,6-dienoic acid (Adda), portion of the MCs has been exploited to develop a strategy to analyze the entirety. Oxidation of MCs causes the cleavage of MC Adda to form 2-methyl-3-methoxy-4-phenylbutanoic acid (MMPB). In the present study, we investigated the kinetics of MMPB produced by oxidation of the most-often-studied MC variant, MC-LR (L = leucine, R = arginine), with permanganate-periodate. This investigation allowed insight regarding the influence of the reaction conditions (concentration of the reactants, temperature, and pH) on the conversion rate. The results indicated that the reaction was second order overall and first order with respect to both permanganate and MC-LR. The second-order rate constant ranged from 0.66 to 1.35 M/s at temperatures from 10 to 30 degrees C, and the activation energy was 24.44 kJ/mol. The rates of MMPB production can be accelerated through increasing reaction temperature and oxidant concentration, and sufficient periodate is necessary for the formation of MMPB. The initial reaction rate under alkaline and neutral conditions is higher than that under acidic conditions, but the former decreases faster than the latter except under weakly acidic conditions. These results provided new insight concerning selection of the permanganate-periodate concentration, pH, and temperature needed for the oxidation of MCs with a high and stable yield of MMPB.; Microcystins (MCs) are a family of related cyclic hepatotoxic heptapeptides, of which more than 70 types have been identified. The chemically unique nature of the C20 beta-amino acid, (2S, 3S, 8S, 9S)-3-amino-9-methoxy-2,6,8-trimethyl-10-phenyldeca4,6-dienoic acid (Adda), portion of the MCs has been exploited to develop a strategy to analyze the entirety. Oxidation of MCs causes the cleavage of MC Adda to form 2-methyl-3-methoxy-4-phenylbutanoic acid (MMPB). In the present study, we investigated the kinetics of MMPB produced by oxidation of the most-often-studied MC variant, MC-LR (L = leucine, R = arginine), with permanganate-periodate. This investigation allowed insight regarding the influence of the reaction conditions (concentration of the reactants, temperature, and pH) on the conversion rate. The results indicated that the reaction was second order overall and first order with respect to both permanganate and MC-LR. The second-order rate constant ranged from 0.66 to 1.35 M/s at temperatures from 10 to 30 degrees C, and the activation energy was 24.44 kJ/mol. The rates of MMPB production can be accelerated through increasing reaction temperature and oxidant concentration, and sufficient periodate is necessary for the formation of MMPB. The initial reaction rate under alkaline and neutral conditions is higher than that under acidic conditions, but the former decreases faster than the latter except under weakly acidic conditions. These results provided new insight concerning selection of the permanganate-periodate concentration, pH, and temperature needed for the oxidation of MCs with a high and stable yield of MMPB.
SubtypeArticle
KeywordMicrocystin 2-methyl-3-methoxy-4-phenylbutanoic Acid Permanganate-periodate Oxidation Kinetics
Department[Wu, Xingqiang; Xiao, Bangding; Gong, Yan; Wang, Zhi; Li, Renhui] Chinese Acad Sci, Inst Hydrobiol, Wuhan 430072, Hubei, Peoples R China; [Wu, Xingqiang; Xiao, Bangding; Gong, Yan; Wang, Zhi] Chinese Acad Sci, Grad Sch, Beijing 100039, Peoples R China; [Chen, Xiaoguo] Wuhan Univ Technol, Wuhan 430070, Hubei, Peoples R China
Subject AreaEnvironmental Sciences ; Toxicology
WOS HeadingsScience & Technology ; Life Sciences & Biomedicine
Funding OrganizationNational Key Project for Basic Research on the Processes of Lake Eutrophication ; Mechanism of Cyanobacterial Blooming [2002CB412300]; Chinese Academy of Sciences [KZCX2-YW-426]; National High Technology Research and Development Program of China [2005AA60101005] ; National Key Project for Basic Research on the Processes of Lake Eutrophication ; Mechanism of Cyanobacterial Blooming [2002CB412300]; Chinese Academy of Sciences [KZCX2-YW-426]; National High Technology Research and Development Program of China [2005AA60101005] ; National Key Project for Basic Research on the Processes of Lake Eutrophication ; Mechanism of Cyanobacterial Blooming [2002CB412300]; Chinese Academy of Sciences [KZCX2-YW-426]; National High Technology Research and Development Program of China [2005AA60101005] ; National Key Project for Basic Research on the Processes of Lake Eutrophication ; Mechanism of Cyanobacterial Blooming [2002CB412300]; Chinese Academy of Sciences [KZCX2-YW-426]; National High Technology Research and Development Program of China [2005AA60101005]
Indexed BySCI
Language英语
WOS Research AreaEnvironmental Sciences & Ecology ; Toxicology
WOS SubjectEnvironmental Sciences ; Toxicology
WOS IDWOS:000259295700005
WOS KeywordPERIODATE-PERMANGANATE OXIDATIONS ; BLUE-GREEN-ALGAE ; POTASSIUM-PERMANGANATE ; CYANOBACTERIAL TOXINS ; MECHANISM ; BIOACCUMULATION ; HYDROCARBONS ; INHIBITION ; TISSUES ; WATER
Funding OrganizationNational Key Project for Basic Research on the Processes of Lake Eutrophication ; Mechanism of Cyanobacterial Blooming [2002CB412300]; Chinese Academy of Sciences [KZCX2-YW-426]; National High Technology Research and Development Program of China [2005AA60101005] ; National Key Project for Basic Research on the Processes of Lake Eutrophication ; Mechanism of Cyanobacterial Blooming [2002CB412300]; Chinese Academy of Sciences [KZCX2-YW-426]; National High Technology Research and Development Program of China [2005AA60101005] ; National Key Project for Basic Research on the Processes of Lake Eutrophication ; Mechanism of Cyanobacterial Blooming [2002CB412300]; Chinese Academy of Sciences [KZCX2-YW-426]; National High Technology Research and Development Program of China [2005AA60101005] ; National Key Project for Basic Research on the Processes of Lake Eutrophication ; Mechanism of Cyanobacterial Blooming [2002CB412300]; Chinese Academy of Sciences [KZCX2-YW-426]; National High Technology Research and Development Program of China [2005AA60101005]
Citation statistics
Cited Times:18[WOS]   [WOS Record]     [Related Records in WOS]
Document Type期刊论文
Identifierhttp://ir.ihb.ac.cn/handle/152342/8006
Collection期刊论文
Corresponding AuthorXiao, BD, Chinese Acad Sci, Inst Hydrobiol, Wuhan 430072, Hubei, Peoples R China
Affiliation1.Chinese Acad Sci, Inst Hydrobiol, Wuhan 430072, Hubei, Peoples R China
2.Chinese Acad Sci, Grad Sch, Beijing 100039, Peoples R China
3.Wuhan Univ Technol, Wuhan 430070, Hubei, Peoples R China
Recommended Citation
GB/T 7714
Wu, Xingqiang,Xiao, Bangding,Gong, Yan,et al. Kinetic study of the 2-methyl-3-methoxy-4-phenylbutanoic acid produced by oxidation of microcystin in aqueous solutions[J]. ENVIRONMENTAL TOXICOLOGY AND CHEMISTRY,2008,27(10):2019-2026.
APA Wu, Xingqiang.,Xiao, Bangding.,Gong, Yan.,Wang, Zhi.,Chen, Xiaoguo.,...&Xiao, BD, Chinese Acad Sci, Inst Hydrobiol, Wuhan 430072, Hubei, Peoples R China.(2008).Kinetic study of the 2-methyl-3-methoxy-4-phenylbutanoic acid produced by oxidation of microcystin in aqueous solutions.ENVIRONMENTAL TOXICOLOGY AND CHEMISTRY,27(10),2019-2026.
MLA Wu, Xingqiang,et al."Kinetic study of the 2-methyl-3-methoxy-4-phenylbutanoic acid produced by oxidation of microcystin in aqueous solutions".ENVIRONMENTAL TOXICOLOGY AND CHEMISTRY 27.10(2008):2019-2026.
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