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Digitale Medien

A Molecular-Dynamics Simulation of the Complex Formation between Methyl (R)/(S)-2-Chloropropionate and Heptakis(3-O-acetyl-2,6-di-O-pentyl)-β-cyclodextrin (1994)

Köhler, Jutta E. H. ; Hohla, Manfred ; Richters, Martina ; [weitere]

Weinheim : Wiley-Blackwell

Berichte der deutschen chemischen Gesellschaft 127 (1994), S. 119-126

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ISSN: 0009-2940

Schlagwort(e): Host-guest complexes ; Molecular-dynamics (MD) simulation ; Enantioselective gas chromatography ; Cyclodextrins ; Chemistry ; Inorganic Chemistry

Quelle: Wiley InterScience Backfile Collection 1832-2000

Thema: Chemie und Pharmazie

Notizen: The energies of complexation of methyl (R)/(S)-2-chloropropionate [(R)/(S)-2] with heptakis(3-O-acetyl-2,6-di-O-pentyl)-β-cyclodextrin (1) and the structures of the corresponding complexes were determined by molecular-dynamcis (MD) simulations at 300 and 333 K. The geometry of the complexes, the conformations of complexed and uncomplexed 1 and (R)/(S)-2 and the closest H-H distances between host and guest in the complexes were determined from the trajectories. The results correspond to the experimental findings from enantioselective gas chromatography.

Zusätzliches Material: 9 Ill.

Materialart: Digitale Medien

URL: http://dx.doi.org/10.1002/cber.19941270120

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Digitale Medien

Gas chromatographic enantiomer separation with modified cyclodextrins: Carboxylic acid esters and epoxides (1993)

König, Wilfried A. ; Gehrcke, Bärbel

Weinheim : Wiley-Blackwell

Journal of High Resolution Chromatography 16 (1993), S. 175-181

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ISSN: 0935-6304

Schlagwort(e): Enantioselective gas chromatography ; 2,6-di-O-methyl-3-O-pentyl-β- and y-cyclodextrins ; α and β hydroxy acids ; Branched carboxylic acids ; Non-steroidal anti-inflammatory drugs ; Abscisic Acid ; Epoxides ; Chemistry ; Analytical Chemistry and Spectroscopy

Quelle: Wiley InterScience Backfile Collection 1832-2000

Thema: Chemie und Pharmazie

Notizen: The wide range of application of 2,6-di-O-methyl-3-O-pentyl-β-and y-cyclodextrins is demonstrated by the resolution of the enantiomers of the methyl esters of chiral carboxylic acids: α and β hydroxy acids with up to 18 carbon atoms, hydroxy di- and tricarboxylic acids, and alkyl/aryl-substituted carboxylic acid methyl esters, including the plant hormone abscisic acid, insect juvenile hormones, and some non-steroidal anti-inflammatory drugs can be resolved with generally large separation factors. The new cyclodextrin derivatives also exhibit high selectivity for epoxides.

Zusätzliches Material: 10 Ill.

Materialart: Digitale Medien

URL: http://dx.doi.org/10.1002/jhrc.1240160309

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Digitale Medien

Cyclodextrins as chiral stationary phases in capillary gas chromatography. Part VII: Cyclodextrins with an inverse substitution pattern - synthesis and enantioselectivityPart VI, see reference [6]. (1990)

König, Wilfried A. ; Icheln, Detlef ; Runge, Torsten ; [weitere]

Weinheim : Wiley-Blackwell

Journal of High Resolution Chromatography 13 (1990), S. 702-707

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ISSN: 0935-6304

Schlagwort(e): Enantioselective capillary gas chromatography ; Cyclodextrins ; Inverse substitution pattern ; Mechanism of chiral recognition ; Applications ; Chemistry ; Analytical Chemistry and Spectroscopy

Quelle: Wiley InterScience Backfile Collection 1832-2000

Thema: Chemie und Pharmazie

Notizen: Transferring the site of specific substitution of dipentylated cyclodextrins with methyl or acyl residues from the secondary 3-hydroxyl group to the primary 6-hydroxyl group was expected to provide new information on the mechanism of chiral recognition. The 3-position points towards and the 6-position points away from the cyclodextrin cavity which via inclusion complex formation is supposed to play a major role in chiral separation. The “inverse” 6-O-acyl-2,3-di-O-pentyl-cyclodextrins displayed almost no enantioselectivity but the corresponding 6-O-methyl derivatives are a versatile supplement to the chiral capillary GC phases nowadays available. Among the compounds that could be enantiomerically resolved are alcohols, amino acids, alkyl halides, bicyclic ethers, acetals, olefins, other hydrocarbons and chiral pharmaceuticals.

Zusätzliches Material: 9 Ill.

Materialart: Digitale Medien

URL: http://dx.doi.org/10.1002/jhrc.1240131010

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