In situ synthesis of di-n-butyl l-tartrate–boric acid complex chiral selector and its application in chiral microemulsion electrokinetic chromatography

Hu, Shaoqiang; Chen, Yonglei; Zhu, Hua-dong; Zhu, Jing; Yan, Na; Chen, Xingguo

doi:10.1016/j.chroma.2009.09.036

Cited by 35 publications

(35 citation statements)

References 36 publications

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“…Therefore, the real chiral selector is the complex of di-n-butyl D-tartrate and boric acid instead of di-n-butyl D-tartrate itself. This is because di-n-butyl D-tartrate molecule has two adjacent hydroxyl groups able to react with boric acid to produce a complex acid, resulting in the enantioselectivity for the chiral analytes [13][14][15]. The effects of the concentration of di-n-butyl D-tartrate and sodium tetraborate on the migration time (t) and chiral resolution (R s ) was investigated in the range of 0-30 mM (0.8%, w/v) and 0-50 mM, respectively ( Table 2).…”

Section: Choice Of Chiral Selector and Effects Of Di-n-butyl D-tartramentioning

confidence: 99%

“…As di-n-butyl D-tartrate is a low interfacial tension oil, a transparent and stable microemulsion could be prepared without a cosurfactant. So cosurfactant 1-butanol was finally not used in the microemulsion, being the same as in Hu's work [13][14][15], where cationic surfactant TTAB was used.…”

Section: Effects Of Surfactant and Cosurfactantmentioning

confidence: 99%

“…As all these compounds are basic drugs of pKa *9, the increase of buffer pH decreases their degree of ionization to produce positively charged ions, and weakens their electrostatic interaction with negatively charged chiral selector, which is unfavorable for chiral separation. Thus, the proper pH is significant for enantioseparation [13][14][15]. The effect of microemulsion pH from 7.0 to 9.0 on enantioseparation was investigated.…”

Section: Effect Of Buffer Phmentioning

confidence: 99%

“…Due to its poor solubility in water, dialkyltartrate only has ever been used together with boric acid on enantioselective extraction of some b-blockers [11,12] or chiral MEEKC of some b-blockers and structurally related compounds [13][14][15] and chiral nonaqueous capillary electrophoresis (NACE) of some b-blockers and b-agonists [16]. But there is no published paper reporting the enantioseparation using di-n-butyl D-tartrate-boric acid as the chiral selector in MEEKC for the enantioseparation of b-agonists.…”

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confidence: 99%

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Enantioseparation of Three β-Agonists Using Di-n-butyl d-Tartrate-Boric Acid Complex as Chiral Selector by Means of MEEKC

et al. 2012

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In this study, a self-prepared complex chiral selector, di-n-butyl D-tartrate-boric acid complex, by the reaction of di-n-butyl D-tartrate with boric acid in a running buffer was used as a chiral selector for the enantioseparation of three b-agonists including clenbuterol, cycloclenbuterol and tulobuterol by means of microemulsion electrokinetic chromatography (MEEKC). Three b-agonists were successfully enantioseparated using the chiral system, indicating that the di-n-butyl D-tartrate-boric acid complex was a useful chiral selector. The effects of di-nbutyl D-tartrate and sodium tetraborate concentration, surfactant concentration, cosurfactant, phosphate, buffer pH and composition, as well as applied voltage were extensively investigated to achieve a good enantioseparation. The di-n-butyl D-tartrate and sodium tetraborate concentration in the running buffer had great influence on the chiral resolution (R s ). Three b-agonists which could not be separated with only di-n-butyl D-tartrate, obtained good chiral separation using the complex chiral selector; among them, two pairs including clenbuterol and cycloclenbuterol could be baseline resolved in 7 min under optimized experimental conditions of 0.8% (w/v) di-n-butyl D-tartrate, 40 mM sodium tetraborate, 3.0% (w/v) Tween-20 and 60 mM sodium dihydrogen phosphate with 25 kV as running voltage. The results indicated that the method could be used for the enantioseparation of three b-agonists.

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Section: Choice Of Chiral Selector and Effects Of Di-n-butyl D-tartramentioning

confidence: 99%

Section: Effects Of Surfactant and Cosurfactantmentioning

confidence: 99%

Section: Effect Of Buffer Phmentioning

confidence: 99%

mentioning

confidence: 99%

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Enantioseparation of Three β-Agonists Using Di-n-butyl d-Tartrate-Boric Acid Complex as Chiral Selector by Means of MEEKC

et al. 2012

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“…Hu's group [69] developed tartaric acid esters as chiral oils in MEEKC. While microemulsions composed of tetradecyl trimethyl ammonium bromide (TTAB), n-dibutyl-L-tartrate and n-butanol did not show chiral recognition in phosphate buffer or tris buffer, the enantiomers of several β-blocker drugs were separated in borate buffer.…”

Section: New Chiral Selectors and Mechanistic Modelsmentioning

confidence: 99%

Chiral electromigration techniques in pharmaceutical and biomedical analysis

Scriba

2011

Bioanal Rev

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Capillary electromigration techniques are often considered ideal methods for enantioseparations due to their high separation selectivity and flexibility. Thus, numerous methods employing a chiral selector as pseudostationary phase in a background electrolyte have been developed and applied for the chiral analysis of drugs in bulk ware, pharmaceutical formulations and biological matrices. Furthermore, electromigration techniques have been combined with spectroscopic methods such as nuclear magnetic resonance in order to understand the complexation of analytes by chiral selectors. The present review focuses on recent developments and applications of chiral electromigration techniques in pharmaceutical and biomedical analysis including examples illustrating analyte-selector complex formation or mechanistic studies which have been published between January 2009 and July 2011. Selector-mediated chiral separations clearly dominate while no applications of capillary electrochromatography to pharmaceutical or biomedical analysis have been reported during this period of time.

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Recent developments in the methodology and application of MEEKC

Ryan

McEvoy²,

Donegan

et al. 2010

Electrophoresis

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MEEKC is an electrodriven separation technique that utilises the unique properties of a microemulsion (ME) as a background electrolyte to achieve separation of a diverse range of solutes. MEs are composed of nanometre-sized oil droplets suspended in aqueous buffer, which is commonly referred to as oil-in-water ME. The droplets are stabilised by the presence of both a surfactant and co-surfactant. The use of water-in-oil MEs in MEEKC has also been investigated. This review details the advances in MEEKC-based separations from the period June 2008 - June 2010. Areas covered include online sample concentration, suppressed electroosmosis MEEKC, chiral separations, MEEKC-MS, MEEKC-ICP-MS and ME structure characterisation. The review also includes a fundamental introduction to MEEKC, along with a review of recent applications.

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In situ synthesis of di-n-butyl l-tartrate–boric acid complex chiral selector and its application in chiral microemulsion electrokinetic chromatography

Cited by 35 publications

References 36 publications

Enantioseparation of Three β-Agonists Using Di-n-butyl d-Tartrate-Boric Acid Complex as Chiral Selector by Means of MEEKC

Enantioseparation of Three β-Agonists Using Di-n-butyl d-Tartrate-Boric Acid Complex as Chiral Selector by Means of MEEKC

Chiral electromigration techniques in pharmaceutical and biomedical analysis

Recent developments in the methodology and application of MEEKC

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