Direct Enantiomer Resolution of Hydroxy and Carbonyl Compounds by Gas Chromatography on Chirasil‐Val

Koppenhoefer, Bernhard; Allmendinger, Hans; Nicholson, Graeme

doi:10.1002/anie.198500481

Cited by 26 publications

(9 citation statements)

References 19 publications

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“…Although these conclusions derive from experiments on a tripodal trispeptide selector, we trust that they are of relevance also to single- stranded diamide phases, because the behavior of the tripodal selector and diamide selectors (i.e., Chirasil-Val) is analogous in terms of separation factor ratios and elution orders. [6][7][8] The findings represented here on the involvement of hydrogen bonds in selector-solute interactions are believed to contribute to the future development of superior chiral phases.…”

Section: Discussionmentioning

confidence: 92%

“…8,16 Although extensive investigations on the resolution mechanism of Chirasil-Val were performed, including thermodynamic analysis of retention data as well as conformational analysis of both solute and selector, 17-19 a reliable model for the resolution of racemic amino acids on Chirasil-Val 20 and on other diamide phases is still lacking. One of the difficulties is the lack of detailed structural information on the diamide selectors commonly used.…”

Section: -13mentioning

confidence: 99%

“…5 The resulting polymeric CSP Chirasil-Val exhibited excellent properties for gas chromatographic enantiomer separation of several classes of chiral compounds that are able to hydrogen bond over a broad temperature range. [6][7][8] Further developments of Chirasil-Val used essentially the same concept, although the chiral selector, the linkage of the chiral selector to the siloxane, or the nature of the siloxane itself was varied. [9][10][11][12][13] In the early days, the three-point interaction model had been used to construct chiral recognition models.…”

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confidence: 98%

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Tripodal trispeptide selector as a model for establishing the importance of hydrogen-bonding in enantiomer-separation

et al. 1998

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Section: Discussionmentioning

confidence: 92%

Section: -13mentioning

confidence: 99%

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Tripodal trispeptide selector as a model for establishing the importance of hydrogen-bonding in enantiomer-separation

et al. 1998

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“…Gas chromatography was performed on a Perkin-Elmer Model Sigma 1 and a Carlo-Erba Model 2001 AC gas chromatograph. Samples of N-trifluoroacetyl amino acid isopropyl esters were eluted from a 26 m, 0.25 mm i.d., df = 0.3 µ , glass capillary column coated with L-Chirasil-Val (15,16). Samples of alcohols were eluted on a 33 m, 0.25 mm i.d., homemade glass capillary column coated with immobilized methylethenylpolysiloxane (17).…”

Section: Methodsmentioning

confidence: 99%

Overtake phenomena in the movement process of components under temperature programming gas chromatography

Lin¹,

Bing-chang²,

Koppenhoefer³

1988

Anal. Chem.

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The movement of a particular component along a chromatographic column Is studied on the basis of the equilibrium equation. Numerical simulations of temperature programming gas chromatography are performed by means of a computer program. The thermodynamic parameters of each component are used to calculate step by step the location x as a fraction of the column length for a given time f. Diagrams for x versus f and dx/df versus f display the movement process of the different components along the column. The validity of this approach Is exemplified for some amino ackt enantiomers and for a series of homologous alcohols. Under the condition of temperature programming, overtake phenomena are observed frequently. Thus, a component lagging behind at low temperature may catch up with and eventually overtake the component running In front when the temperature Is raised.

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“…Esta columna permitió la separación de todos los aminoácidos proteínicos racémicos en un cromatograma tomando sólo 30 minutos [27]. La columna Chirasil-Val fue usada para separar muchas otras mezclas quirales incluyendo los arilglicoles, metabolitos de fármacos, ácidos 2-y 3-hidroxicarboxílicos [28] y muchas sustancias no derivadas como los alcoholes, dicetonas e hidroxi lactonas [29].…”

Section: Figura 14 Estructura Del Polisiloxano L-valina-tert-butilaunclassified

Desarrollo de columnas capilares quirales para su empleo en cromatografía de gases: aplicación a la separación de contaminantes ambientales quirales

Menestrina¹

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El objetivo principal de este trabajo de tesis fue el desarrollo de columnas capilares conteniendo fases estacionarias quirales para su uso en cromatografía de gases (CG) que puedan ser usadas en el análisis enantiomérico de múltiples familias químicas de compuestos, principalmente sustancias de interés ambiental. Objetivos específicos: ✓ Desarrollo de columnas capilares conteniendo como fase estacionaria derivados β- y de γ-ciclodextrinas disueltos en un solvente polimérico aquiral y depositados sobre la pared interna del capilar en películas de espesor controlado. ✓ Caracterización de las propiedades cromatográficas de los capilares preparados: eficiencia, selectividad, estabilidad y reproducibilidad. ✓ Medición de constantes de asociación enantiómero/selector a distintas temperaturas. Determinación de la verdadera enantioselectividad sin el uso de hipótesis ad-hoc. Determinación de las propiedades termodinámicas que describen estas asociaciones. ✓ Comparación de las constantes absolutas obtenidas a una dada temperatura con los valores que se obtendrían a partir del modelo de incremento de la retención a la misma temperatura. Evaluación crítica de los resultados. ✓ Estudio de la influencia ejercida por la matriz polimérica aquiral sobre la enantioselectividad aparente para distintos racematos y, eventualmente, en el mecanismo de enantiorreconocimiento. ✓ Aplicación a la separación y análisis enantiomérico de contaminantes ambientales quirales.

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Direct Enantiomer Resolution of Hydroxy and Carbonyl Compounds by Gas Chromatography on Chirasil‐Val

Cited by 26 publications

References 19 publications

Tripodal trispeptide selector as a model for establishing the importance of hydrogen-bonding in enantiomer-separation

Tripodal trispeptide selector as a model for establishing the importance of hydrogen-bonding in enantiomer-separation

Overtake phenomena in the movement process of components under temperature programming gas chromatography

Desarrollo de columnas capilares quirales para su empleo en cromatografía de gases: aplicación a la separación de contaminantes ambientales quirales

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