Chiral separation of γ-butyrolactone derivatives by gas chromatography on 2,3-di-O-methyl-6-O-tert.-butyldimethylsilyl-β-cyclodextrin

Ramos, Mônica Freiman de Souza; Teixeira, Lis H. P.; Neto, Francisco Radler de Aquino; Barreiro, Eliezer J.; Rodrigues, Carlos Rangel; Fraga, Carlos A.M.

doi:10.1016/s0021-9673(02)01824-1

Cited by 12 publications

(3 citation statements)

References 15 publications

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“…The recent rapid development of the monolith column has resulted in a variety of applications, including use as a separator column for chiral compounds. Chiral compounds can be separated by gas chromatography, [1][2][3] high performance liquid chromatography (HPLC), [4][5][6][7] and capillary electrophoresis. [8][9][10] Polymer-based monolith columns can be used as separator columns for chiral compounds.…”

Section: Introductionmentioning

confidence: 99%

Modification of monolithic stationary phase using human serum albumin as chiral separation

Septiana

Angga

Amalia

et al. 2018

AIP Conference Proceedings

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Section: Introductionmentioning

confidence: 99%

Modification of monolithic stationary phase using human serum albumin as chiral separation

Septiana

Angga

Amalia

et al. 2018

AIP Conference Proceedings

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“…Limitations of indirect method are demand of the pure chiral reagent, the availability of functional groups of enantiomers for the reaction and long analysis time for preparation and identification. Therefore, direct separation using high performance liquid chromatography (HPLC) [4][5][6], capillary electrophoresis (CE) [7][8][9][10] or gas chromatography (GC) [11][12][13][14][15][16] are preferred techniques for the analysis of enantiomeric purity of chiral analytes. For volatile and thermally stable organic compounds, GC is the most suitable technique.…”

Section: Enantiomeric Separation By Gas Chromatographymentioning

confidence: 99%

“…Analysis of enantiomer purity using separation techniques, such as chromatography or electrophoresis, could be performed directly or indirectly. The direct method using chiral selectors as stationary phases or chiral resolving agents was achieved with high performance liquid chromatography (HPLC) [4][5][6], capillary electrophoresis (CE) [7][8][9][10] or gas chromatography (GC) [11][12][13][14][15][16]. For volatile and thermally stable organic compounds, such as alcohols, GC is the preferred technique with the use of derivatized cyclodextrins (CDs) as chiral stationary phases [8][9][10][11][12][13][14][15][16][17].…”

Section: Introductionmentioning

confidence: 99%

Enantiomeric separation of alcohols by gas chromatography and QSPR study to predict enantiomeric separation

Toboonpha

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Enantiomeric separation of 55 alcohols (13 aliphatic alcohols and 42 alcohols of aromatic structure) was studied by gas chromatography using octakis(2,3-di-O-acetyl-6-O-tert-butyldimethylsilyl)-?-CD (or GSiAc) as a chiral stationary phase. For separation under temperature program, 44 alcohols could be enantioseparated. The only aliphatic alcohol that could be completely separated into their enantiomers was 2-hexanol. Twenty-five alcohols, based on 1-phenylethanol, were selected to study under isothermal conditions. For halogen-substituted 1-phenylethanols, temperature strongly affected enantioselectivities of para-substituted alcohols. However, temperature affected enantioselectivities of methyl- or trifluoromethyl-substituted alcohols at ortho-position more than other positions. For para-substituted alcohols, enantioseparations could be improved with the substituent in the order of halogen > trifluoromethyl > alkyl > phenyl. In addition, temperature affected enantioselectivities of alcohols with small alkyl substitution at the stereogenic center rather than bulky alkyl or phenyl group. Attempt to find model that can predict enantioseparations of these alcohols was made using several molecular modeling techniques. From molecular docking calculations, the best predictive model has an accuracy of 83.64 %. MD simulations were applied for only 5 selected alcohols with different enantioselectivities and the results showed no relationship with enantioselectivity. For QSPR studies, excellent models to predict elution temperatures of the less retained and the more retained enantiomers were developed with the average errors of only 2.30 and 2.68 degrees Celsius, respectively.

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Functionalized assembly of solid membranes for chiral separation using polyelectrolytes and chiral ionic liquid

Meng

Ling

et al. 2013

AIChE Journal

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in Wiley Online Library (wileyonlinelibrary.com).The successful assembly of a new solid membrane for chiral separation, assembled via the formation of complexes of a polyelectrolyte and b-cyclodextrins chiral ionic liquid (b-CD-IL) is presented. Before the assembly, the b-CD-IL, used as a chiral selector, was synthesized and characterized by 1 H NMR. To tune the chiral separation capability of the solid membrane, b-CD-IL was subsequently immobilized on to porous supporting membranes through layer-by-layer assembly of the b-CD-IL and polyelectrolytes. The resulting membrane was used in the chiral separation of D, L-tryptophan racemate enantiomer. The membrane structure and surface morphologies were systematically analyzed by FT-IR, UV-vis, SEM and AFM. The effects of layer number on the chiral separation were investigated. It was found that the more b-CD-IL was immobilized on the membranes; the higher average separation factor could be obtained. The stability of the multilayer membrane was improved by coating with crosslinked polymer layer.

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Chiral separation of γ-butyrolactone derivatives by gas chromatography on 2,3-di-O-methyl-6-O-tert.-butyldimethylsilyl-β-cyclodextrin

Cited by 12 publications

References 15 publications

Modification of monolithic stationary phase using human serum albumin as chiral separation

Modification of monolithic stationary phase using human serum albumin as chiral separation

Enantiomeric separation of alcohols by gas chromatography and QSPR study to predict enantiomeric separation

Functionalized assembly of solid membranes for chiral separation using polyelectrolytes and chiral ionic liquid

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