| 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 Publication | ENVIRONMENTAL TOXICOLOGY AND CHEMISTRY
 |
| ISSN | 0730-7268 |
| Volume | 27Issue:10Pages:2019-2026 |
| Abstract | 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.; 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. |
| Subtype | Article |
| Keyword | Microcystin 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 Area | Environmental Sciences ; Toxicology |
| WOS Headings | Science & Technology ; Life Sciences & Biomedicine |
| Funding Organization | 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] ; 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 By | SCI |
| Language | 英语 |
| WOS Research Area | Environmental Sciences & Ecology ; Toxicology |
| WOS Subject | Environmental Sciences ; Toxicology |
| WOS ID | WOS:000259295700005 |
| WOS Keyword | PERIODATE-PERMANGANATE OXIDATIONS ; BLUE-GREEN-ALGAE ; POTASSIUM-PERMANGANATE ; CYANOBACTERIAL TOXINS ; MECHANISM ; BIOACCUMULATION ; HYDROCARBONS ; INHIBITION ; TISSUES ; WATER |
| Funding Organization | 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] ; 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 | |
| Document Type | 期刊论文 |
| Identifier | http://ir.ihb.ac.cn/handle/152342/8006 |
| Collection | 期刊论文 |
| Corresponding Author | Xiao, BD, Chinese Acad Sci, Inst Hydrobiol, Wuhan 430072, Hubei, Peoples R China |
| Affiliation | 1.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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