(S)-(+)-2-Octanol as a Chiral Oil Core for the Microemulsion Electrokinetic Chromatographic Separation of Chiral Basic Drugs

Threeprom, Jirasak

doi:10.2116/analsci.23.1071

Cited by 8 publications

(7 citation statements)

References 28 publications

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“…After 2.5 h, the conversion was 83% and full conversion (>99% ee ) was observed after a reaction time of <16 h. Enantiomerically pure lipophilic alcohols can be used as derivatizing agent for the enantioseparation of carboxylic acids [23] or e.g., for the preparation of functional materials. ( S )-2-Octanol, for instance, was used as the chiral selector in microemulsion electrokinetic chromatography [24]. The ( R )-enantiomer served as a precursor for chiral liquid crystals [25].…”

Section: Resultsmentioning

confidence: 99%

Enantiocomplementary Yarrowia lipolytica Oxidoreductases: Alcohol Dehydrogenase 2 and Short Chain Dehydrogenase/Reductase

et al. 2013

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Enzymes of the non-conventional yeast Yarrowia lipolytica seem to be tailor-made for the conversion of lipophilic substrates. Herein, we cloned and overexpressed the Zn-dependent alcohol dehydrogenase ADH2 from Yarrowia lipolytica in Escherichia coli. The purified enzyme was characterized in vitro. The substrate scope for YlADH2 mediated oxidation and reduction was investigated spectrophotometrically and the enzyme showed a broader substrate range than its homolog from Saccharomyces cerevisiae. A preference for secondary compared to primary alcohols in oxidation direction was observed for YlADH2. 2-Octanone was investigated in reduction mode in detail. Remarkably, YlADH2 displays perfect (S)-selectivity and together with a highly (R)-selective short chain dehydrogenase/ reductase from Yarrowia lipolytica it is possible to access both enantiomers of 2-octanol in >99% ee with Yarrowia lipolytica oxidoreductases.

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Section: Resultsmentioning

confidence: 99%

Enantiocomplementary Yarrowia lipolytica Oxidoreductases: Alcohol Dehydrogenase 2 and Short Chain Dehydrogenase/Reductase

et al. 2013

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“…However, some water‐soluble solvents as ethyl acetate , isopropylmyristate , and propylene glycol monomethyl ether acetate were reported in MEEKC studies. For enantiomer separation, chiral oils were often preferred, such as ( S )‐(+)‐2‐octanol , ( R )‐(–)‐2‐octanol , and diethyl tartrate . In the last decade, substitutes for organic solvents appeared and novel IL/W MEs used in MEEKC were developed .…”

Section: Microemulsion Compositionsmentioning

confidence: 99%

“…separated ephedrine enantiomers using MEEKC with a chiral oil, (2R, 3R)‐di‐ n ‐butyl tartrate in 1993 . Subsequently, chiral surfactant, chiral oil, or chiral co‐surfactant has been applied to achieve good resolution of stereoisomers, respectively . In those studies, methylpseudoephedrine, ephedrine, (±)‐norphenylephrine, (±)‐ephedrine, and other compounds were all well separated using chiral surfactant or chiral oil.…”

Section: Applicationsmentioning

confidence: 99%

Twenty‐one years of microemulsion electrokinetic chromatography (1991–2012): A powerful analytical tool

et al. 2013

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Microemulsion electrokinetic chromatography (MEEKC) is a CE separation technique, which utilizes buffered microemulsions as the separation media. In the past two decades, MEEKC has blossomed into a powerful separation technique for the analysis of a wide range of compounds. Pseudostationary phase composition is so critical to successful resolution in EKC, and several variables could be optimized including surfactant/co-surfactant/oil type and concentration, buffer content, and pH value. Additionally, MEEKC coupled with online sample preconcentration approaches could significantly improve the detection sensitivity. This review comprehensively describes the development of MEEKC from the period 1991 to 2012. Areas covered include basic theory, microemulsion composition, improving resolution and enhancing sensitivity methods, detection techniques, and applications of MEEKC.

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“…The effect of co‐surfactant was also examined in the work by Threeprom 54 for the separation of enantiomers of norephedrine, ephedrine, propranolol and synephrine. The chiral selectand was present in the form of ( S )‐2‐octanol as the oil phase.…”

Section: Recent Developments In Achieving Chiral Separations Using mentioning

confidence: 99%

Recent advances in the methodology, optimisation and application of MEEKC

et al. 2009

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MEEKC is an electrodriven separation technique. Oil-in-water microemulsions (MEs) and to a lesser extent water-in-oil MEs have been used in MEEKC as BGEs to achieve separation of a diverse range of solutes. The more common (oil-in-water) MEs are composed of nanometre-sized droplets of oil suspended in an aqueous buffer. Interfacial tension between the oil and aqueous phase is reduced close to zero by the presence of a surfactant and a co-surfactant. MEEKC is capable of providing fast and efficient separations for a wide range of acidic, basic and neutral, water-soluble and -insoluble compounds. This review details the advances in MEEKC-based separations from the period 2006 to 2008. Areas covered include online sample concentration, chiral separation, suppressed electroosmosis MEEKC, MEEKC-MS, and the use of MEEKC in predicting migration behaviour and solute characteristics. A fundamental introduction to MEEKC, along with the presentation and discussion of recent applications is also included.

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(S)-(+)-2-Octanol as a Chiral Oil Core for the Microemulsion Electrokinetic Chromatographic Separation of Chiral Basic Drugs

Cited by 8 publications

References 28 publications

Enantiocomplementary Yarrowia lipolytica Oxidoreductases: Alcohol Dehydrogenase 2 and Short Chain Dehydrogenase/Reductase

Enantiocomplementary Yarrowia lipolytica Oxidoreductases: Alcohol Dehydrogenase 2 and Short Chain Dehydrogenase/Reductase

Twenty‐one years of microemulsion electrokinetic chromatography (1991–2012): A powerful analytical tool

Recent advances in the methodology, optimisation and application of MEEKC

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