Computer-aided optimisation of drug enantiomer separation in chiral high-performance liquid chromatography

Fell, Anthony F.; Noctor, T. A. G.; Mama, J.E.; Clark, Brian J.

doi:10.1016/s0378-4347(88)80004-5

Cited by 58 publications

(13 citation statements)

References 6 publications

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“…The influence of formic acid in the solution was also investigated as it is known that it can improve ionization. Chemometric approach, based on the use of a matrix of experiments by which variations of all factors can be studied simultaneously, [17] has been used. Using this method, the number of experiments can be significantly reduced.…”

Section: Optimization Of the Ms Conditions Before Lc Couplingmentioning

confidence: 99%

Regioisomer characterization of triacylglycerols by non‐aqueous reversed‐phase liquid chromatography/electrospray ionization mass spectrometry using silver nitrate as a postcolumn reagent

2010

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Triacylglycerols (TAGs) provide a challenge for mass spectrometry (MS) analysis because of their complexity. In particular, for dietary, nutritional and metabolic purposes, the positional placement of fatty acids on the glycerol backbone of TAGs is a crucial aspect. To solve this problem, we have investigated the TAGs' fragmentation patterns using an ion trap mass spectrometer. A series of pure regioisomeric pairs of TAGs (POP/PPO, POO/OPO and OSO/SOO) were cationized by Ag(+) after their separation by non-aqueous reversed-phase liquid chromatography (NARP-LC) before MS to improve MS sensitivity. Electrospray ionization-MS (ESI-MS) conditions were optimized in order to produce characteristic [M + Ag + AgNO(3)](+) ions from each TAG, which were then fragmented to produce MS/MS spectra and then fragmented further to produce up to MS(5) spectra. The observation of ions produced by LC-MS(5) of on-line Ag(+)-cationized TAG provided unambiguous information on the fatty acid distribution on the glycerol backbone. These strategies of MS to MS(5) experiments were applied to identify components and to determine the regiospecificity of TAG within a complex mixture of lipids in natural oils.

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Section: Optimization Of the Ms Conditions Before Lc Couplingmentioning

confidence: 99%

Regioisomer characterization of triacylglycerols by non‐aqueous reversed‐phase liquid chromatography/electrospray ionization mass spectrometry using silver nitrate as a postcolumn reagent

2010

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“…Hydrophobic interactions of drugs with AGP often require the addition of an organic solvent in the mobile phase in order to reduce analysis time. Acetonitrile and isopropranol (IPA) are frequently used with AGP [42][43][44] and, as reported in Table 4, enantioselectivity and retention factors decreased drastically when the percentage of IPA in the mobile phase increased. Thus, as already demonstrated for other basic compounds, 38,40,45 hydrophobic interactions are involved in the stereoselective retention of methadone with AGP.…”

Section: Chiral Agpmentioning

confidence: 99%

Chiral stationary phases in HPLC for the stereoselective determination of methadone

Rudaz

Veuthey

1999

Chirality

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“…The pharmacologically active S( § enantiomer had a 100-200-fold higher apparent affinity to the binding site than the pharmacologically weak R(-) enantiomer [1 2]. The coupling of this C3 hydroxy group to Dglucuronic acid in the body does not affect the chiral centre, and results in diastereomeric glucuronide conjugates as demonstrated by Ruelius et al [3], Mascher et al [4], and Fell et al [5]. Because of their high water solubility the glucuronides are considered to be pharmacologically inactive.…”

Section: Introductionmentioning

confidence: 99%

Direct high pressure liquid chromatographic analysis and preliminary pharmacokinetics of enantiomers of oxazepam and temazepam with their corresponding glucuronide conjugates

Vree

Baars²,

Wuis³

1991

Pharmaceutisch Weekblad Scientific Edition

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Three high pressure liquid chromatographic systems for the separation of oxazepam, temazepam and their glucuronides (system A), the separation of their R,S glucuronide diastereomers (system B) and the chiral separation of the parent drugs (system C) are described. Preliminary pharmacokinetics of R,S-oxazepam and R,S-temazepam in a human volunteer reveal that the protein binding of the glucuronides is lower than that of the parent drugs, but that there is no difference in protein binding between the R-oxazepam/temazepam and S-oxazepam/temazepam and their corresponding glucuronides. The S-glucuronide is the main metabolite formed and excreted by man. The plasma ratio R/S-glucuronide is 1:1 for both oxazepam and temazepam. The renal clearance of R-temazepam, and S-temazepam are similar, and those of R-oxazepam and S-oxazepam tend to be different.

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Computer-aided optimisation of drug enantiomer separation in chiral high-performance liquid chromatography

Cited by 58 publications

References 6 publications

Regioisomer characterization of triacylglycerols by non‐aqueous reversed‐phase liquid chromatography/electrospray ionization mass spectrometry using silver nitrate as a postcolumn reagent

Regioisomer characterization of triacylglycerols by non‐aqueous reversed‐phase liquid chromatography/electrospray ionization mass spectrometry using silver nitrate as a postcolumn reagent

Chiral stationary phases in HPLC for the stereoselective determination of methadone

Direct high pressure liquid chromatographic analysis and preliminary pharmacokinetics of enantiomers of oxazepam and temazepam with their corresponding glucuronide conjugates

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