RP-HPLC and NMR study of cis–trans isomerization of enalaprilat

Bouabdallah, Sondes; Trabelsi, H.; Dhia, T. Ben; Sabbah, S.; Bouzouita, K; Khaddar, R.

doi:10.1016/s0731-7085(02)00661-1

Cited by 17 publications

(10 citation statements)

References 27 publications

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“…The latter is stabilized by hydrogen bonding between the carbonyl (40) and the hydrogen of hydroxyl group OH of the acid function (56). This result is in agreement with other studies reported on a similar product such as enalapril [5]. …”

Section: Resultssupporting

confidence: 94%

“…This result is similar to those reported earlier demonstrating that high temperature was useful for elution of proline-containing substances as a single peak [7, 11, 35]. Conversely, a low temperature is known to have a potential effect on the separation of isomers [5, 9, 36–39]. …”

Section: Resultssupporting

confidence: 91%

“…A similar study demonstrated this correspondence in the case of ramiprilat [4], enalaprilat [5], and perindopril [39] in different solvents.…”

Section: Resultsmentioning

confidence: 55%

“…The trans form in lisinopril was shown to be the preferred isomer and biologically active [4–6]. The assignment separation of cis and trans form of lisinopril has been carried out by HPLC [5, 7–12], CZE [13–16], and NMR spectroscopy [2, 17–22]. The latter technique is a powerful tool and has been widely applied for structural and stereochemical characterization of amino acids, oligo- and polypeptides [23–26].…”

Section: Introductionmentioning

confidence: 99%

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Study of a Conformational Equilibrium of Lisinopril by HPLC, NMR, and DFT

Bouabdallah¹,

Dhia

Driss³

2014

International Journal of Analytical Chemistry

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The isomerization of lisinopril has been investigated using chromatographic, NMR spectroscopic, and theoretical calculations. The NMR data, particularly the NOEDIFF experiments, show that the major species that was eluted first is the trans form. The proportion was 77% and 23% for the trans and cis, respectively. The thermodynamic parameters (ΔH, ΔS, and ΔG) were determined by varying the temperature in the NMR experiments. The interpretations of the experimental data were further supported by DFT/B3LYP calculations.

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Section: Resultssupporting

confidence: 94%

Section: Resultssupporting

confidence: 91%

“…A similar study demonstrated this correspondence in the case of ramiprilat [4], enalaprilat [5], and perindopril [39] in different solvents.…”

Section: Resultsmentioning

confidence: 55%

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Study of a Conformational Equilibrium of Lisinopril by HPLC, NMR, and DFT

Bouabdallah¹,

Dhia

Driss³

2014

International Journal of Analytical Chemistry

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“…The cis-trans isomerisation of the DF may be attributed to the hindered rotation around the amide bond. Such phenomenon has been observed in HPLC analysis for enalapril and lisinopril [12,13].…”

Section: Cis-trans Isomerizationmentioning

confidence: 62%

Stability indicating reversed-phase liquid chromatographic determination of metronidazole benzoate and diloxanide furoate as bulk drug and in suspension dosage form

Mishal¹,

Sober²

2005

Journal of Pharmaceutical and Biomedical Analysis

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Interconversion of Stereochemically Labile Enantiomers (Enantiomerization)

Trapp

2013

Topics in Current Chemistry

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The investigation of the molecular dynamics of stereoisomers is of fundamental interest in chemistry, biochemistry, medicine, and related areas. In recent years enantioselective dynamic chromatography and enantioselective dynamic capillary electrophoresis (DCE) have been established as versatile tools to investigate the kinetics of interconversions of stereoisomers. The term dynamic chromatography and dynamic electrophoresis, following the term dynamic NMR (DNMR) (Grathwohl and Wüthrich, Biopolymers 20:2623-2633, 1981; Wüthrich, Angew Chem Int Ed 42:3340-3363, 2003; Binsch et al., Angew Chem Int Ed 10:570-572, 1971), stresses the dynamic (Herschbach, Angew Chem Int Ed 26:1221-1243, 1987) behavior of analytes to interconvert between two stereoisomeric forms during the separation process. If the interconversion process is slow compared to the separation of the enantiomers, which can be achieved by accelerating the separation process or lowering the temperature, partial separation with characteristic plateau formation or peak broadening is observed.This chapter gives an overview of recent advances in the study of stereodynamics of molecules by dynamic chromatography (Trapp et al., Chirality 13:403-414, 2001; D'Acquarica et al., J Sep Sci 29:1508-1516, 2006; Wolf, Chem Soc Rev 34:595-608, 2005; Wolf, Dynamic stereochemistry of chiral compounds - principles and applications. RSC Publishing, Cambridge, 2008) and capillary electrophoresis. Models and algorithms to evaluate interconversion profiles obtained by separation techniques are discussed with respect to the challenging demands of high separation efficiencies typical of modern separation techniques. Models used for evaluation are based on iterative computer simulation algorithms using the theoretical plate model (TPM) or stochastic model of chromatography, empirical calculation methods, derived from equations used in chemical engineering, namely Damköhler analysis, and direct access using the approximation function, and more recently the unified equation of chromatography, which can be applied to all kinds of first-order reactions taking place during a chromatographic or electrophoretic separation. Furthermore, areas of applications to investigate stereodynamic processes are presented and discussed to give a practical guide for using dynamic chromatography and capillary electrophoresis.

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RP-HPLC and NMR study of cis–trans isomerization of enalaprilat

Cited by 17 publications

References 27 publications

Study of a Conformational Equilibrium of Lisinopril by HPLC, NMR, and DFT

Study of a Conformational Equilibrium of Lisinopril by HPLC, NMR, and DFT

Stability indicating reversed-phase liquid chromatographic determination of metronidazole benzoate and diloxanide furoate as bulk drug and in suspension dosage form

Interconversion of Stereochemically Labile Enantiomers (Enantiomerization)

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