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学科主题: Environmental Sciences; Toxicology
题名: Kinetic study of the 2-methyl-3-methoxy-4-phenylbutanoic acid produced by oxidation of microcystin in aqueous solutions
作者: Wu, Xingqiang1, 2; Xiao, Bangding1, 2; Gong, Yan1, 2; Wang, Zhi1, 2; Chen, Xiaoguo3; Li, Renhui1
通讯作者: Xiao, BD, Chinese Acad Sci, Inst Hydrobiol, Wuhan 430072, Hubei, Peoples R China
关键词: microcystin ; 2-methyl-3-methoxy-4-phenylbutanoic acid ; permanganate-periodate ; oxidation ; kinetics
刊名: ENVIRONMENTAL TOXICOLOGY AND CHEMISTRY
发表日期: 2008-10-01
卷: 27, 期:10, 页:2019-2026
收录类别: SCI
文章类型: Article
部门归属: [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
WOS标题词: Science & Technology ; Life Sciences & Biomedicine
资助者: 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]
类目[WOS]: Environmental Sciences ; Toxicology
研究领域[WOS]: Environmental Sciences & Ecology ; Toxicology
摘要: 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.
英文摘要: 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.
关键词[WOS]: PERIODATE-PERMANGANATE OXIDATIONS ; BLUE-GREEN-ALGAE ; POTASSIUM-PERMANGANATE ; CYANOBACTERIAL TOXINS ; MECHANISM ; BIOACCUMULATION ; HYDROCARBONS ; INHIBITION ; TISSUES ; WATER
语种: 英语
WOS记录号: WOS:000259295700005
ISSN号: 0730-7268
Citation statistics:
内容类型: 期刊论文
URI标识: http://ir.ihb.ac.cn/handle/152342/8006
Appears in Collections:中科院水生所知识产出(2009年前)_期刊论文

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作者单位: 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:
Wu, Xingqiang; Xiao, Bangding; Gong, Yan; Wang, Zhi; Chen, Xiaoguo; Li, Renhui.Kinetic study of the 2-methyl-3-methoxy-4-phenylbutanoic acid produced by oxidation of microcystin in aqueous solutions,ENVIRONMENTAL TOXICOLOGY AND CHEMISTRY,2008,27(10):2019-2026
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