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Transformation and products of captopril with humic constituents during laccase-catalyzed oxidation: Role of reactive intermediates
Du, Penghui1,2; Zhao, He1; Liu, Chenming1; Huang, Qingguo3; Cao, Hongbin1
2016-12-01
Source PublicationWATER RESEARCH
ISSN0043-1354
Volume106Issue:DECPages:488-495
Abstract

The transformation of captopril (CAP), a widely-used thiol drug, was studied with the presence of dissolved model humic constituents (HCs) in a laccase-catalyzed system. Reaction products were analyzed by ultra-performance liquid chromatography coupled to time-of-flight mass spectrometry and condensed fukui function computation. CAP reacted with different model HCs in the enzymatic system for 1 h, ranging from 75% (syringic acid) to 96% (p-coumaric acid). In the absence of HCs, only 15% of CAP was removed through self-coupling. The presence of HCs apparently changed the transformation of CAP in aqueous environment, and the HC reactive intermediates played an important role. First, during laccase catalysis, HCs with different structures were oxidized to produce reactive intermediates, including phenoxyl radical cation, ortho-, and pars-quinone intermediates. Second, these intermediates were readily attacked by CAP via nucleophilic reactions, forming C-S-C covalent conjugates. More importantly, the standard reduction potential of these intermediates is a critical parameter, as PCA showed the highest reactivity to the nucleophilic addition reaction with CAP by forming phenoxy radical cations. While SYR showed the least reactivity due to the formation of pars-quinone intermediates. Therefore, the functional groups on HCs could greatly influence the cross-coupling with CAP, as well as the type and stability of the coupling products. This work clearly demonstrated the transformation of CAP and other thiol drugs with the presence of HCs in aqueous environment, which is similar to the natural humification process. (C) 2016 Elsevier Ltd. All rights reserved.

KeywordCaptopril Humic Constitutes Laccase Cross-coupling Nucleophilic Reaction
SubtypeArticle
WOS HeadingsScience & Technology ; Technology ; Life Sciences & Biomedicine ; Physical Sciences
DOI10.1016/j.watres.2016.10.036
Indexed BySCI
Language英语
WOS KeywordPERSONAL CARE PRODUCTS ; COVALENT BINDING ; WASTE-WATER ; HALOGENATED PHENOLS ; ANTIOXIDANT PROPERTIES ; BIOMIMETIC CATALYSIS ; SYRINGIC ACID ; FREE-RADICALS ; SUBSTANCES ; MODEL
WOS Research AreaEngineering ; Environmental Sciences & Ecology ; Water Resources
WOS SubjectEngineering, Environmental ; Environmental Sciences ; Water Resources
Funding OrganizationNational Natural Science Foundation of China(51108441 ; 51209191 ; 51102238 ; 51378487)
WOS IDWOS:000388047500050
Citation statistics
Cited Times:12[WOS]   [WOS Record]     [Related Records in WOS]
Document Type期刊论文
Identifierhttp://ir.ipe.ac.cn/handle/122111/21825
Collection湿法冶金清洁生产技术国家工程实验室
Affiliation1.Chinese Acad Sci, Beijing Engn Res Ctr Proc Pollut Control, Inst Proc Engn, Div Environm Technol & Engn, Beijing 100190, Peoples R China
2.Univ Chinese Acad Sci, Beijing 100049, Peoples R China
3.Univ Georgia, Dept Crop & Soil Sci, Coll Agr & Environm Sci, Griffin, GA 30223 USA
Recommended Citation
GB/T 7714
Du, Penghui,Zhao, He,Liu, Chenming,et al. Transformation and products of captopril with humic constituents during laccase-catalyzed oxidation: Role of reactive intermediates[J]. WATER RESEARCH,2016,106(DEC):488-495.
APA Du, Penghui,Zhao, He,Liu, Chenming,Huang, Qingguo,&Cao, Hongbin.(2016).Transformation and products of captopril with humic constituents during laccase-catalyzed oxidation: Role of reactive intermediates.WATER RESEARCH,106(DEC),488-495.
MLA Du, Penghui,et al."Transformation and products of captopril with humic constituents during laccase-catalyzed oxidation: Role of reactive intermediates".WATER RESEARCH 106.DEC(2016):488-495.
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