CEC enantioseparations on chiral monolithic columns: A study of the stereoselective degradation of (R/S)-dichlorprop [2-(2,4-dichlorophenoxy)propionic acid] in soil

Antonella Messina, Massimo Sinibaldi

Research output: Contribution to journalArticle

Abstract

For the study of the stereoselective degradation of the herbicide 2-aryloxipropionic acid dichlorprop (DCPP) in soil, a porous monolithic chiral column (100 μm id) was prepared by in situ copolymerization of glycidyl methacrylate, methyl methacrylate and ethylene glycol dimethacrylate in the presence of formamide and 1-propanol as the porogen solvents. Subsequently, the epoxide groups at the surface of the monolith were reacted with (+)-1-(4-aminobutyl)-(5R,8S,10R)-terguride as the chiral selector. Optimum conditions for the herbicide resolution by CEC were found using mobile phases consisting of acetic acid/ triethylamine mixtures in ACN-methanol (9:1 v/v). Under these conditions fully separation of DCPP enantiomers in the presence of clofibric acid (internal standard) was achieved in about 5 min. Experiments on the incubation of rac-DCPP in soil at room temperature showed the herbicide undergone during 23 incubation days to a degradation to levels ≤20% of the initial concentration, with rates for (R)-DCPP slower than (S)-DCPP. More interesting results were observed when herbicide enantiomers were individually incubated. In both the experiments, the formation of the opposite isomer in the presence of the initial one, and reversed enantiomeric interconversion in the case of (S)-DCPP was observed. (R)-DCPP was found to be the most persistent isomer after incubation.

Original languageEnglish
Pages (from-to)2613-2618
Number of pages6
JournalElectrophoresis
Volume28
Issue number15
DOIs
Publication statusPublished - Aug 2007

Fingerprint

Soil
Soils
Degradation
Herbicides
Enantiomers
Isomers
Clofibric Acid
1-Propanol
Methacrylates
Epoxy Compounds
dichlorprop
Acetic Acid
Copolymerization
Methanol
Experiments
Temperature
Acids

Keywords

  • CEC enantioseparations
  • Chiral monolithic column
  • Dichlorprop
  • Soil
  • Stereoselective degradation

ASJC Scopus subject areas

  • Clinical Biochemistry

Cite this

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title = "CEC enantioseparations on chiral monolithic columns: A study of the stereoselective degradation of (R/S)-dichlorprop [2-(2,4-dichlorophenoxy)propionic acid] in soil",
abstract = "For the study of the stereoselective degradation of the herbicide 2-aryloxipropionic acid dichlorprop (DCPP) in soil, a porous monolithic chiral column (100 μm id) was prepared by in situ copolymerization of glycidyl methacrylate, methyl methacrylate and ethylene glycol dimethacrylate in the presence of formamide and 1-propanol as the porogen solvents. Subsequently, the epoxide groups at the surface of the monolith were reacted with (+)-1-(4-aminobutyl)-(5R,8S,10R)-terguride as the chiral selector. Optimum conditions for the herbicide resolution by CEC were found using mobile phases consisting of acetic acid/ triethylamine mixtures in ACN-methanol (9:1 v/v). Under these conditions fully separation of DCPP enantiomers in the presence of clofibric acid (internal standard) was achieved in about 5 min. Experiments on the incubation of rac-DCPP in soil at room temperature showed the herbicide undergone during 23 incubation days to a degradation to levels ≤20{\%} of the initial concentration, with rates for (R)-DCPP slower than (S)-DCPP. More interesting results were observed when herbicide enantiomers were individually incubated. In both the experiments, the formation of the opposite isomer in the presence of the initial one, and reversed enantiomeric interconversion in the case of (S)-DCPP was observed. (R)-DCPP was found to be the most persistent isomer after incubation.",
keywords = "CEC enantioseparations, Chiral monolithic column, Dichlorprop, Soil, Stereoselective degradation",
author = "Antonella Messina and Massimo Sinibaldi",
year = "2007",
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language = "English",
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T1 - CEC enantioseparations on chiral monolithic columns

T2 - A study of the stereoselective degradation of (R/S)-dichlorprop [2-(2,4-dichlorophenoxy)propionic acid] in soil

AU - Messina, Antonella

AU - Sinibaldi, Massimo

PY - 2007/8

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N2 - For the study of the stereoselective degradation of the herbicide 2-aryloxipropionic acid dichlorprop (DCPP) in soil, a porous monolithic chiral column (100 μm id) was prepared by in situ copolymerization of glycidyl methacrylate, methyl methacrylate and ethylene glycol dimethacrylate in the presence of formamide and 1-propanol as the porogen solvents. Subsequently, the epoxide groups at the surface of the monolith were reacted with (+)-1-(4-aminobutyl)-(5R,8S,10R)-terguride as the chiral selector. Optimum conditions for the herbicide resolution by CEC were found using mobile phases consisting of acetic acid/ triethylamine mixtures in ACN-methanol (9:1 v/v). Under these conditions fully separation of DCPP enantiomers in the presence of clofibric acid (internal standard) was achieved in about 5 min. Experiments on the incubation of rac-DCPP in soil at room temperature showed the herbicide undergone during 23 incubation days to a degradation to levels ≤20% of the initial concentration, with rates for (R)-DCPP slower than (S)-DCPP. More interesting results were observed when herbicide enantiomers were individually incubated. In both the experiments, the formation of the opposite isomer in the presence of the initial one, and reversed enantiomeric interconversion in the case of (S)-DCPP was observed. (R)-DCPP was found to be the most persistent isomer after incubation.

AB - For the study of the stereoselective degradation of the herbicide 2-aryloxipropionic acid dichlorprop (DCPP) in soil, a porous monolithic chiral column (100 μm id) was prepared by in situ copolymerization of glycidyl methacrylate, methyl methacrylate and ethylene glycol dimethacrylate in the presence of formamide and 1-propanol as the porogen solvents. Subsequently, the epoxide groups at the surface of the monolith were reacted with (+)-1-(4-aminobutyl)-(5R,8S,10R)-terguride as the chiral selector. Optimum conditions for the herbicide resolution by CEC were found using mobile phases consisting of acetic acid/ triethylamine mixtures in ACN-methanol (9:1 v/v). Under these conditions fully separation of DCPP enantiomers in the presence of clofibric acid (internal standard) was achieved in about 5 min. Experiments on the incubation of rac-DCPP in soil at room temperature showed the herbicide undergone during 23 incubation days to a degradation to levels ≤20% of the initial concentration, with rates for (R)-DCPP slower than (S)-DCPP. More interesting results were observed when herbicide enantiomers were individually incubated. In both the experiments, the formation of the opposite isomer in the presence of the initial one, and reversed enantiomeric interconversion in the case of (S)-DCPP was observed. (R)-DCPP was found to be the most persistent isomer after incubation.

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