Practical resolution of enantiomers by high-performance liquid chromatography

Yamamoto, Chiyo

doi:10.1007/978-1-4020-2337-8_10

Cited by 12 publications

(8 citation statements)

References 83 publications

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“…5,6 Among the many polymeric CSPs, the phenylcarbamates and benzoates of cellulose and amylose are known to show a high chiral recognition to a broad range of chiral compounds. [6][7][8][9][10][11][12] Cellulose and amylose are stereoregular polymers consisting of D-glucose, although their chiral recognition abilities are not high enough to be used as CSPs. However, their hydroxy groups can be readily converted to phenylcarbamates and benzoates through reaction with phenyl isocyanates and benzoyl chlorides, respectively.…”

Section: Introductionmentioning

confidence: 99%

Enantioseparation using urea‐ and imide‐bearing chitosan phenylcarbamate derivatives as chiral stationary phases for high‐performance liquid chromatography

Yamamoto¹,

Fujisawa²,

Kamigaito³

2007

Chirality

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Completely deacetylated chitosan was prepared by the treatment of commercial chitosan with 50% aqueous NaOH, and then derivatized into several new chitosan phenylcarbamate derivatives having a urea and an imide moiety at the 2-position of the glucosamine ring by the reaction with isocyanate and phthalic anhydride/isocyanate, respectively. The chitosan derivatives were coated on macroporous silica gel and evaluated as chiral stationary phases (CSPs) for high-performance liquid chromatography. The chiral recognition ability of the chitosan derivative was improved using the completely deacetylated chitosan. Among the novel chitosan derivatives, the 3,5-dimethyl-, 3,5-dichloro-, and 3,4-dichlorophenylcarbamate derivatives were found to possess relatively high chiral resolution abilities. The CSPs based on the chitosan phenylcarbamate-urea and -imide derivatives were stable in the presence of chloroform and ethyl acetate as a component of the eluents, and some racemates were better resolved by such eluents. The dichlorophenylcarbamate-imide derivatives showed a high chiral recognition for metal acetylacetonate complexes. The enantiomerization of Al(acac)3 was performed on the chitosan 3,5-dichlorophenylcarbamate-imide derivative CSP and the resulting chromatogram showed a 26% (+)-isomer enrichment.

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Section: Introductionmentioning

confidence: 99%

Enantioseparation using urea‐ and imide‐bearing chitosan phenylcarbamate derivatives as chiral stationary phases for high‐performance liquid chromatography

Yamamoto¹,

Fujisawa²,

Kamigaito³

2007

Chirality

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“…The absence of an isolation problem of separated compound from the solvent is especially beneficial for volatile racemates like those of chiral inhalation anesthetics. However, preparative enantioselective GC does not match the overwhelming success of preparative enantioselective LC [34,35]. The preparative GC method has only been successful for racemates exhibiting enantioseparation factors α > 1.5 [33].…”

Section: Analytical Gas-chromatographic Enantioseparation Of Enfluranmentioning

confidence: 98%

Salient Features of Enantioselective Gas Chromatography: The Enantiomeric Differentiation of Chiral Inhalation Anesthetics as a Representative Methodological Case in Point

Schurig

2013

Topics in Current Chemistry

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The enantiomeric differentiation of the volatile chiral inhalation anesthetics enflurane, isoflurane, and desflurane by analytical and preparative gas chromatography on various modified cyclodextrins is described. Very large enantioseparation factors α are obtained on the chiral selector octakis(3-O-butanoyl-2,6-di-O-pentyl)-γ-cyclodextrin (Lipodex E). The gas-chromatographically observed enantioselectivities are corroborated by NMR-spectroscopy using Lipodex E as chiral solvating agent and by various sensor devices using Lipodex E as sensitive chiral coating layer. The assignment of the absolute configuration of desflurane is clarified. Methods are described for the determination of the enantiomeric distribution of chiral inhalation anesthetics during narcosis in clinical trials. The quantitation of enantiomers in a sample by the method of enantiomeric labeling is outlined. Reliable thermodynamic parameters of enantioselectivity are determined by using the retention-increment R' approach for the enantiomeric differentiation of various chiral halocarbon selectands on diluted cyclodextrin selectors.

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“…As for analytical chiral separations surveyed between 1960 and 2000, enantioselective GC preceded the routine use but was then surpassed by enantioselective LC and enantioselective electromigration methods [228]. A survey of the analytical methods used in the determination of enantiomeric composition required by the journal Tetrahedron Asymmetry for 1995 (322 entries), 1999 (357 entries), and 2002 (290 entries) gave the following data: HPLC (118,146,129), NMR (104,79,60), chiral GC (66,85,66), polarimetry (35,30,24), and others (35,30,24) [229]. Today, analytical enantioselective GC is undoubtedly of widespread use as judged from the availability of commercial capillary columns containing chiral stationary phases by all leading suppliers of gas chromatographic items.…”

Section: Some Statisticsmentioning

confidence: 99%

“…Contrary to liquid chromatography (LC), the recovery of isolated enantiomers from the gaseous mobile phase (carrier gas) is straightforward when aerosol and mist formation is prevented by using specially designed collection vessels [24]. The GC approach does not match the overwhelming success of preparative enantioseparation achieved in the realm of LC [229,230]. Modern commercial instrumentation for preparative-scale GC is not available.…”

Section: Preparative-scale Gas Chromatographic Enantioseparationmentioning

confidence: 99%

Separation of Enantiomers by Gas Chromatography on Chiral Stationary Phases

Schurig

2010

Chiral Separation Methods for Pharmaceutical and Biotechnological Products

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Practical resolution of enantiomers by high-performance liquid chromatography

Cited by 12 publications

References 83 publications

Enantioseparation using urea‐ and imide‐bearing chitosan phenylcarbamate derivatives as chiral stationary phases for high‐performance liquid chromatography

Enantioseparation using urea‐ and imide‐bearing chitosan phenylcarbamate derivatives as chiral stationary phases for high‐performance liquid chromatography

Salient Features of Enantioselective Gas Chromatography: The Enantiomeric Differentiation of Chiral Inhalation Anesthetics as a Representative Methodological Case in Point

Separation of Enantiomers by Gas Chromatography on Chiral Stationary Phases

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