Mechanistic aspects of chiral discrimination by surface-immobilized ?1-acid glycoprotein

Waters, Marjorie S.; Sidler, Daniel R.; Simon, Ágnes; Middaugh, C. Russell; Thompson, Richard A.; August, L.J.; Bicker, G.; Perpall, Holly J.; Grinberg, Nelu

doi:10.1002/(sici)1520-636x(1999)11:3<224::aid-chir9>3.0.co;2-e

Cited by 23 publications

(16 citation statements)

References 49 publications

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“…In another study, it was reported that Van't Hoff plot of α on AGP columns was non-linear for chiral drugs bearing a carboxyl group and a quinoline moiety [120]. In a temperature range from 35 to 45 • C, the separation was enthalpy-dominated.…”

Section: Protein-based Csps For the Separation Of Basic Neutral And mentioning

confidence: 97%

“…It should be noted that the enantioselectivity of RfBP-CSPs for arylpropionic anti-inflammatory drugs is generally poor (except for indoprofen) while the warfarin enantiomers have been resolved with a selectivity of 2.59 [119]. Interesting results have been reported by Waters et al for the enantioseparation of chiral drugs bearing a carboxyl group (pK a = 4.5) and a quinoline moiety (pK a = 5.1) using an AGP-CSP [120]. Surprisingly, high enantioselectivities were observed at a pH beyond 5.0, although AGP and drug enantiomers were both negatively charged.…”

Section: Protein-based Csps For the Separation Of Basic Neutral And mentioning

confidence: 99%

“…Moreover, Hermansson suggested in the case of arylpropionic acid derivatives, that ion-pair distribution of these compounds, with sodium as counter ion, was the dominant retention mechanism on AGP columns [123]. Regarding the enantioselectivity of AGP, OVM, avidin and RfBP stationary phases, this parameter is generally little affected by the buffer concentration suggesting that coulombic interactions and ion-pair distribution are not the major driving forces in chiral discrimination [92,102,103,113,116,120]. Despite this, non-negligible concentration effects have also been reported by Hermansson's group for AGP columns [123,124].…”

Section: Protein-based Csps For the Separation Of Basic Neutral And mentioning

confidence: 99%

“…In most cases, the retention factors and selectivity decrease in the presence of organic solvents for both AGP [70,105,120,123], OVM [109,113,118], avidin [83,113] and RfBP [93] chiral stationary phases. This can be attributed to a reduction of hydrophobic interactions between the enantiomers and protein-based CSP as the mobile phase becomes less polar.…”

Section: Protein-based Csps For the Separation Of Basic Neutral And mentioning

confidence: 99%

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Separation of drug enantiomers by liquid chromatography and capillary electrophoresis, using immobilized proteins as chiral selectors

Millot

2003

Journal of Chromatography B

134

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Section: Protein-based Csps For the Separation Of Basic Neutral And mentioning

confidence: 97%

Section: Protein-based Csps For the Separation Of Basic Neutral And mentioning

confidence: 99%

Section: Protein-based Csps For the Separation Of Basic Neutral And mentioning

confidence: 99%

Section: Protein-based Csps For the Separation Of Basic Neutral And mentioning

confidence: 99%

See 2 more Smart Citations

Separation of drug enantiomers by liquid chromatography and capillary electrophoresis, using immobilized proteins as chiral selectors

Millot

2003

Journal of Chromatography B

134

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“…It has been suggested that retention and enantioselectivity in protein-based chiral stationary phases depend on hydrophobic interactions, hydrogen bonding, ionic bonding and ion-pairing interactions. 13 In the present study, several polysaccharide-and protein-based chiral columns were evaluated for the resolution of some drugs and their metabolites (Figure 1). The influence of mobile phase composition on retention and chiral resolution was also evaluated.…”

Section: Introductionmentioning

confidence: 99%

Enantiomeric Resolution of Drugs and Metabolites in Polysaccharide- and Protein-Based Chiral Stationary Phases

Bonato¹,

Bortocan²,

Gaitani³

et al. 2002

J. Braz. Chem. Soc.

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Várias fases estacionárias baseadas em derivados de polissacarídeos e proteínas foram avaliadas para a resolução de alguns fármacos quirais e seus metabólitos. As fases estacionárias baseadas em polissacarídeos CHIRALCEL OD-H, CHIRALCEL OB-H, CHIRALCEL OJ, CHIRALPAK AD e CHIRALPAK AS foram avaliadas em condições de fase normal, usando hexano:2-propanol como fase móvel. Dietilamina ou ácido trifluoracético foram adicionados para melhorar a simetria dos picos. As colunas CHIRALCEL OJ-R, CHIRALCEL OD-R e CHIRALCEL OD-H foram avaliadas em condições de fase reversa, usando acetonitrila:água ou acetonitrila: NaClO 4 . As fases estacionárias baseadas em proteínas CHIRAL AGP e ULTRON ES-OVM foram usadas com fases móveis consistindo de soluções tampão adicionadas de modificadores orgânicos. Entre as fases estacionárias baseadas em derivados de polissacarídeos, a CHIRALPAK AD mostrou melhor resolução de quase todos os fármacos e metabólitos estudados. A coluna ULTRON ES-OVM foi particularmente útil para a resolução dos quatro estereoisômeros da tioridazina-2-sulfóxido.Several chiral stationary phases based on polysaccharide derivatives and proteins were evaluated for the resolution of some chiral drugs and their metabolites. The polysaccharide-based stationary phases CHIRALCEL OD-H, CHIRALCEL OB-H, CHIRALCEL OJ, CHIRALPAK AD and CHIRALPAK AS were evaluated under normal phase conditions, using hexane:2-propanol or hexane:ethanol as mobile phase. Diethylamine and trifluoracetic acid were also added to improve peak shape. The CHIRALCEL OJ-R, CHIRALCEL OD-R and CHIRALCEL OD-H columns were evaluated under reversed-phase conditions, using acetonitrile:H 2 O or acetonitrile:NaClO 4 solution. The protein-based stationary phases, CHIRAL AGP and ULTRON ES-OVM columns were used with mobile phases consisting of a buffer solution supplemented with an organic modifier. Among the polysaccharide-based stationary phases, CHIRALPAK AD provided better resolution for almost all drugs and metabolites studied. The ULTRON ES-OVM column was particularly suitable for the resolution of the four enantiomers of thioridazine-2-sulfoxide.

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Mechanisms of retention of pyrrolidinyl norephedrine on immobilized ?1-acid glycoprotein

et al. 2000

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Mechanistic aspects of chiral discrimination by surface-immobilized ?1-acid glycoprotein

Cited by 23 publications

References 49 publications

Separation of drug enantiomers by liquid chromatography and capillary electrophoresis, using immobilized proteins as chiral selectors

Separation of drug enantiomers by liquid chromatography and capillary electrophoresis, using immobilized proteins as chiral selectors

Enantiomeric Resolution of Drugs and Metabolites in Polysaccharide- and Protein-Based Chiral Stationary Phases

Mechanisms of retention of pyrrolidinyl norephedrine on immobilized ?1-acid glycoprotein

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