title: Spectroscopic investigations of the chiral interactions of metolachlor and its (S)-isomer with lipase and phosphatase.
abstract: Metolachlor [2-chloro-N-(2-ethyl-6-methylphenyl)-N-(2-methoxy-1-methylethyl) acetamide] is a chiral acetanilide herbicide. We investigated its enantioselective interactions, and that of its (S)-isomer, with Penicillium expansum alkaline lipase and phosphatase. UV differential spectroscopy and fluorescence spectrophotometry studies were conducted in phosphate buffered solution at pH 7. Chiral differences in the UV absorption and fluorescence spectra of lipase and phosphatase with metolachlor and its (S)-isomer were detected. The results showed that the interactions of metolachlor and its (S)-isomer with lipase and phosphatase occur statically through complex formation, and enantioselectivity was clearly observed. In addition, both UV absorption and fluorescence spectrophotometry showed that the (S)-isomer interacted more strongly with lipase and phosphatase than metolachlor.
authors.affiliation: Institute of Environmental Science, Zhejiang University, Hangzhou, China.
authors.forename: Yue Z
authors.initials: YZ
authors.lastname: Wen
authors.forename: Yu L
authors.initials: YL
authors.lastname: Yuan
authors.forename: Hui
authors.initials: H
authors.lastname: Chen
authors.forename: He L
authors.initials: HL
authors.lastname: Wang
authors.forename: Hui J
authors.initials: HJ
authors.lastname: Liu
authors.forename: Xiao D
authors.initials: XD
authors.lastname: Kang
authors.forename: Liu S
authors.initials: LS
authors.lastname: Fu
mesh_terms: D000081:Acetamides / Q000737:chemistry*; D002942:Circular Dichroism; D006540:Herbicides / Q000737:chemistry*; D006863:Hydrogen-Ion Concentration; D007536:Isomerism; D008049:Lipase / Q000737:chemistry / Q000187:drug effects* / Q000378:metabolism; D010407:Penicillium / Q000201:enzymology*; D010744:Phosphoric Monoester Hydrolases / Q000737:chemistry / Q000187:drug effects* / Q000378:metabolism; D013050:Spectrometry, Fluorescence; D013056:Spectrophotometry, Ultraviolet
chemical_list: D000081:Acetamides; D006540:Herbicides; D008049:Lipase; D010744:Phosphoric Monoester Hydrolases; C051786:metolachlor