Gas chromatographic simulated moving bed separation of the enantiomers of the inhalation anesthetic enflurane

Biressi, Giovanni; Quattrini, Francesca; Juza, Markus; Mazzotti, Marco; Schurig, Volker; Morbidelli, Massimo

doi:10.1016/s0009-2509(00)00109-3

Cited by 40 publications

(42 citation statements)

References 20 publications

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“…In an attempt to scale-up the discontinuous preparative GC approach by a continuous enantioseparation of inhalation anesthetics, the simulated moving bed (SMB) technology has been employed in enantioselective GC, adapting the previous findings obtained in the batch-wise processes described above. Preliminary studies included enflurane [52,53] and isoflurane [54], which were enantioseparated on unpurified octakis(3-O-butanoyl-2,6-di-O-pentyl)-γ-cyclodextrin (Lipodex E) diluted in polysiloxane SE-54 and coated on Chromosorb P (AW, DMCS, 80-100 mesh). An optimized version of the enantioselective SMB unit later on consisted of eight 80 cm Â 15 mm (i.d.)…”

Section: Analytical Gas-chromatographic Enantioseparation Of Enfluranmentioning

confidence: 99%

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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Section: Analytical Gas-chromatographic Enantioseparation Of Enfluranmentioning

confidence: 99%

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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“…Also, recent developments related with the operation of SMB units in the gas phase were found to be remarkable, either for fine chemical resolution [107][108][109][110] or for bulk chemicals [111][112][113][114][115][116][117].…”

Section: Smb -Gas and Supercritical Phasesmentioning

confidence: 99%

Simulated Moving Bed Chromatography: From Concept to Proof‐of‐Concept

Gomes

Rodrigues

2011

Chem Eng & Technol

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This work presents a comprehensive insight about simulated moving bed (SMB) technology, from concept to unit operation and process demonstration. A particular relevance is given to SMB nonconventional modes of operation, modeling, and design of SMB-based separations as well as to the construction and operation of SMB units. A conventional separation of a racemic mixture of (S,R)-a-tetralol by means of the FlexSMB-LSRE® unit is addressed to better exemplify a state-ofthe-art SMB lab-scale process development and demonstration.

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“…The semipreparative-scale column (2.3 m63 mm ID) was prepared by applying the procedure described elsewhere [24,25]. In short, the stationary phase was prepared by coating a mixture of 20% w/w of heptakis(2,3-di-O-acetyl-6-O-tert-butyldimethylsilyl)-b-CD and 80% of PS086 on Chromosorb P (80-100 mesh).…”

Section: Preparation Of Columnsmentioning

confidence: 99%

Semipreparative-scale gas-chromatographic separation of filbertone enantiomers

Blanch¹,

Castillo²

2006

J. Sep. Sci.

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The enantioselectivity of heptakis(2,3-di-O-acetyl-6-O-tert-butyldimethylsilyl-beta-CD) toward racemic filbertone (E-5-methyl-hep-2-en-4-one) was studied by performing the chiral separation on a capillary column, a thick-film wide-bore column and a semipreparative column. The semipreparative enantioseparation of filbertone was achieved at 80 degrees C by using a packed column providing (R)- and (S)-enantiomers of filbertone with ee 90 and 96%, respectively. The isolated enantiomers (approximately 250 microg each, ee = 90-96%) may be used for studies on the relationship of chirality and biological activity by olfactory screening and toxicological studies.

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Gas chromatographic simulated moving bed separation of the enantiomers of the inhalation anesthetic enflurane

Cited by 40 publications

References 20 publications

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

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

Simulated Moving Bed Chromatography: From Concept to Proof‐of‐Concept

Semipreparative-scale gas-chromatographic separation of filbertone enantiomers

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