Combining the Enantioselectivities of l -Valine Diamide and Permethylated β-Cyclodextrin in One Gas Chromatographic Chiral Stationary Phase
| Autor: | Pavel A. Levkin, Volker Schurig, and Anna Levkina |
|---|---|
| Rok vydání: | 2006 |
| Předmět: |
Diamide
chemistry.chemical_classification Chromatography Gas Ketone Chromatography Molecular Structure Cyclodextrin Hydrosilylation beta-Cyclodextrins Enantioselective synthesis Stereoisomerism Valine Butylamines Methylation Analytical Chemistry Catalysis chemistry.chemical_compound Hydrocarbon chemistry Alcohols Organic chemistry Gas chromatography Enantiomer |
| Zdroj: | Analytical Chemistry. 78:5143-5148 |
| ISSN: | 1520-6882 0003-2700 |
| DOI: | 10.1021/ac0606148 |
| Popis: | An L-valine diamide chiral selector was attached to a polysiloxane through a long hydrocarbon spacer giving rise to a chiral stationary phase (CSP), Chirasil-Val-C11. The enantioselective properties of this readily accessible diamide CSP under gas chromatographic conditions were found to be similar to that of the commercially available Chirasil-Val CSP prepared by a polymer-analogous route. A new binary CSP, Chirasil-DexVal-C11, was synthesized by means of simultaneous attachment of both the L-valine diamide and permethylated beta-cyclodextrin selectors to a polysiloxane using platinum-catalyzed hydrosilylation, thereby overcoming the immiscibility problem known for Chirasil-Val and Chirasil-Dex. This binary CSP retained both the enantioselectivity of Chirasil-Val-C11 toward alpha-amino acid derivatives and the unsurpassed enantioselectivity of Chirasil-Dex toward underivatized chiral alcohols, ketones, and hydrocarbons. Furthermore, it was shown that the presence of the cyclodextrin selector in Chirasil-Val-C11 significantly improved the enantioseparation of proline, which represented a problematic amino acid on diamide CSPs. |
| Databáze: | OpenAIRE |
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