Probing the chiral separation mechanism and the absolute configuration of malathion, malaoxon and isomalathion enantiomers by chiral high performance liquid chromatography coupled with chiral detector–binding energy computations

Zhang, Anping; Lai, Wenfeng; Sun, Jianqiang; Hu, Guixiang; Liu, Weiping

doi:10.1016/j.chroma.2013.01.016

Cited by 18 publications

(8 citation statements)

References 18 publications

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“…In the perpendicular view to the molecular axis of the gt conformer, a space surrounded by glucopyranose rings and 4-methylbenzoyl groups can be seen. While in some reports concerning CMB [ 21 , 22 ] its gt -conformation was assumed, Zugenmaier had concluded that the gg -conformer is the deepest minimum of CB , and we obtained the same result for both CB and CMB . However, based on several considerations, we too predicted that the gt -conformer—which, we think, may be present at a certain population and/or under dynamic equilibria—must be the adsorption active form.…”

Section: Resultssupporting

confidence: 77%

“…While some reports were published including computer-assisted simulation study of chiral recognition mechanism by polysaccharide-based CSPs [ 20 , 21 , 22 ], we have independently undertaken a simulation study to understand the remarkably different spectrum of separable racemates between “OB-H” and “OJ-H”. The study could also give a rationalization for the above mentioned achiral selectivity of “OJ-H”.…”

Section: Resultsmentioning

confidence: 99%

“…In contrast, the elution pattern on “OJ-H” showed that the retention is strongly affected by the position of the methyl group rather than its presence or absence. Furthermore, the elution pattern on “OJ-H” was not essentially affected by a reversed-phase eluent (i.e., acetonitrile–water 70:30 v / v [ 22 ]), which is common in chiral recognition by a polysaccharide-based CSP [ 27 ]. Thus, each type of stationary phase exhibited an entirely different selection rule: one is physicochemical and the other is geometrical.…”

Section: Resultsmentioning

confidence: 99%

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Achiral Molecular Recognition of Aromatic Position Isomers by Polysaccharide-Based CSPs in Relation to Chiral Recognition

et al. 2016

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Chromatographic separation of several sets of aromatic position isomers on three cellulose- and one amylose-based chiral stationary phases was performed to evaluate the potential of a polysaccharide-based chiral stationary phase (CSP) in the separation of isomeric or closely similar molecules, and to understand the interaction mechanism of this type of CSP with analytes. Their ability of molecular recognition was quite outstanding, but the selection rule was particular to each polysaccharide derivative. In the series of analytes, cellulose tris(4-methylbenzoate) and tris(3,5-dimethylphenylcarbamate) exhibited a contrasting selection rule, and the recognition mechanism was considered based on the computer-simulation of the former polymer.

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Section: Resultssupporting

confidence: 77%

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

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Achiral Molecular Recognition of Aromatic Position Isomers by Polysaccharide-Based CSPs in Relation to Chiral Recognition

et al. 2016

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“…Thus, application of MIPs should be beneficial to the environmental protection and food safety (Tokonami et al 2009;Garcia et al 2011;Li et al 2014;Cheng et al 2014). In organisms, malathion can be metabolized and transformed into more toxic derivative malaxon (Zhang et al 2013). As endocrine-disrupting chemicals (EDCs), the residues of malathion are often detected in natural environments and in food items as well (Kjeldsen et al 2013).…”

Section: Introductionmentioning

confidence: 99%

Preparation of malathion MIP-SPE and its application in environmental analysis

Zuo

Zhu

Zhan

et al. 2015

Environ Monit Assess

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Malathion is an organophosphorous insecticide for controlling insects on fruits and vegetables, miscellaneous household insects, and animal parasites. It is important to develop highly efficient and selective pre-treatment method for analyzing malathion residues in environment and samples from agricultural products based on the molecularly imprinted polymers (MIPs). In this study, we developed a tailor-made MIP method with highly specific recognization to the template. The MIPs were prepared using malathion as a template, methacrylic acid (MAA) as a functional monomer, ethylene glycol dimethacrylate (EGDMA) as a crosslinker, azodiisobutyronitrile (AIBN) as an initiator, and the acetonitrile-chloroform (1:1, v/v) as a porogen. The molecular recognization mechanism of malathion and MAA was evaluated by molecular simulation, ultraviolet spectrometry (UV), and (1)H-nuclear magnetic resonance ((1)H-NMR). MAA interacted specifically with malathion by hydrogen bond with a ratio of 2:1. The MIPs exhibit a high affinity, recognition specificity, and efficient adsorption performance for malathion. The Fourier transform infrared spectroscopy (FT-IR), scanning electron microscope (SEM), surface area and porosimeter analyzer, thermogravimetric/differential thermal analyzer (TG/DTA) were used to characterize the properties of MIP. The malathion residues in soil, tap water, and cabbage were cleaned up by MIP-SPE, detected quantitatively using GC-FPD, and confirmed by GC-MS/MS. The limits of tap water, soil, and cabbage were confined to 0.001 mg L(-1), 0.004 and 0.004 mg kg(-1), respectively. The spiked recoveries of malathion were 96.06-111.49% (with RSD being 5.7-9.2%), 98.13-103.83% (RSD, 3.5-8.7%), and 84.94-93.69% (RSD, 4.7-5.8%) for tap water, soil, and cabbage samples, respectively. Thus, the method developed here can be used effectively in assessing malathion residues in multiple environmental samples. The aim of the study was to provide an efficient, selective, and accurate method for analyzing malathion at trace levels in multiple media.

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“…Hydrophobic groups, including alkyl [1][2][3], aryl [4], and ester moieties, can resize the cavities in CDs by destroying the hydrogen bonded networks. These effects, such as hydrogen bonding, -stacking, and dipole-dipole forces [5], enable the formation of additional interactions between the analytes and the functionalized ␤-CDs. Hydrophilic groups, particularly those arising from the introduction of the hydroxypropyl [6] and other polar groups [7], supply new hydrogen-bonding sites and chiral centers to separate enantiomers with distal chiral carbons.…”

Section: Introductionmentioning

confidence: 99%

Preparation of chiral oxazolinyl-functionalized β-cyclodextrin-bonded stationary phases and their enantioseparation performance in high-performance liquid chromatography

Zhang

Wang

et al. 2016

J. Sep. Science

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Preparation of chiral oxazolinyl-functionalized ␤-cyclodextrin-bonded stationary phases and their enantioseparation performance in high-performance liquid chromatography A simple procedure for the synthesis of three new oxazolinyl-substituted ␤-cyclodextrins (6-deoxy-6-R-(-)-4-phenyl-4,5-dihydrooxazolinyl-␤-cyclodextrin, 6-deoxy-6-S-(-)-4-phenyl-4,5-dihydrooxazolinyl-␤-cyclodextrin, and 6-deoxy-6-S-(-)-(4-pyridin-1-ium-4-methyl-benzenesulphonate)-4,5-dihy-drooxazolinyl-␤-cyclodextrin) and their covalent bonding to silica are reported. The ability of these chiral stationary phase columns for separating compounds is also presented and discussed. Twenty-eight compounds were examined in the polar-organic mobile phase mode, and 11 ␤-nitroethanols were tested in the reversed-phase mode. Excellent enantioseparations were achieved for most of the analytes, even for several challenging compounds. The rigid and flexible structures of mono-substituted chiral groups and the fragments around the rim of the ␤-cyclodextrin cavity played an important role in the separation process. Factors such as -stacking, dipole-dipole interactions, ion-pairing, and steric hindrance effects were found to affect the chromatographic performance. Moreover, the buffer composition, and percentages of organic modifiers in the mobile phase, were investigated and compared. The mechanisms involved in the separation were postulated based on the chromatographic data.

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Probing the chiral separation mechanism and the absolute configuration of malathion, malaoxon and isomalathion enantiomers by chiral high performance liquid chromatography coupled with chiral detector–binding energy computations

Cited by 18 publications

References 18 publications

Achiral Molecular Recognition of Aromatic Position Isomers by Polysaccharide-Based CSPs in Relation to Chiral Recognition

Achiral Molecular Recognition of Aromatic Position Isomers by Polysaccharide-Based CSPs in Relation to Chiral Recognition

Preparation of malathion MIP-SPE and its application in environmental analysis

Preparation of chiral oxazolinyl-functionalized β-cyclodextrin-bonded stationary phases and their enantioseparation performance in high-performance liquid chromatography

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