High-performance liquid chromatographic enantioseparation of unusual amino acid derivatives with axial chirality on polysaccharide-based chiral stationary phases
López-Ram-de-Víu, P. (Universidad de Zaragoza) ; Gálvez, J.A. (Universidad de Zaragoza) ; Díaz-de-Villegas, M.D.
Resumen: The successfulenantioseparationofaxiallychiralaminoacidderivativescontainingacyclohexylidene moiety onan an alyticalandsemipreparativescalewasachievedforthefirsttimebyHPLCusing polysaccharide-based chiral stationary phases. Racemicmethyl N-benzoylamino esters,easilyobtained by methanoly sisof the corresponding 5(4H)-oxazolones, were subject edtochiralHPLCresolutionusing chiral stationaryphasesbasedonimmobilized3,5-dimethylphenylcarbamatederivativesofamylose (Chiralpak® IA column)orcellulose(Chiralpak® IB column). The behaviour of both selectors under dif-ferent elution conditions was evaluated and compared. The amy los ecolumns howed better performance than the cellulose column for allenantiomers tested. These mi preparative resolution of axially chiral amino acidderivatives with different side chains has been achievedona 250mm×20mmIDChiralpak® IA columnusingtheappropriatemixtureof n-hexane/chlorofom/ethanol aseluent by successive injec-tions of asolution of the sample in chloroform. Using this protocol up to 120 m go feachenan tiomer of the correspondingaxiallychiralaminoacidderivativewereobtainedfrom300mgofracemate.[(Sa)-2a, 105 mg;(Ra)-2a, 60mg,[(Sa)-2b, 105mg;(Ra)-2b, 90mg,[(Sa)-2c, 120mg;(Ra)-2c, 100mg].
Idioma: Inglés
DOI: 10.1016/j.chroma.2015.02.055
Año: 2015
Publicado en: Journal of Chromatography A 1390 (2015), 78-85
ISSN: 0021-9673
Factor impacto JCR: 3.926 (2015)
Categ. JCR: CHEMISTRY, ANALYTICAL rank: 11 / 75 = 0.147 (2015) - Q1 - T1
Categ. JCR: BIOCHEMICAL RESEARCH METHODS rank: 14 / 77 = 0.182 (2015) - Q1 - T1
Factor impacto SCIMAGO: 1.693 - Analytical Chemistry (Q1) - Organic Chemistry (Q1) - Medicine (miscellaneous) (Q1) - Biochemistry (Q1)
Financiación: info:eu-repo/grantAgreement/ES/DGA/GAE-102
Tipo y forma: Article (PostPrint)
Área (Departamento): Área Química Orgánica (Dpto. Química Orgánica)
You must give appropriate credit, provide a link to the license, and indicate if changes were made. You may do so in any reasonable manner, but not in any way that suggests the licensor endorses you or your use. You may not use the material for commercial purposes. If you remix, transform, or build upon the material, you must distribute your contributions under the same license as the original.
Exportado de SIDERAL (2021-01-21-11:10:16)
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Idioma: Inglés
DOI: 10.1016/j.chroma.2015.02.055
Año: 2015
Publicado en: Journal of Chromatography A 1390 (2015), 78-85
ISSN: 0021-9673
Factor impacto JCR: 3.926 (2015)
Categ. JCR: CHEMISTRY, ANALYTICAL rank: 11 / 75 = 0.147 (2015) - Q1 - T1
Categ. JCR: BIOCHEMICAL RESEARCH METHODS rank: 14 / 77 = 0.182 (2015) - Q1 - T1
Factor impacto SCIMAGO: 1.693 - Analytical Chemistry (Q1) - Organic Chemistry (Q1) - Medicine (miscellaneous) (Q1) - Biochemistry (Q1)
Financiación: info:eu-repo/grantAgreement/ES/DGA/GAE-102
Tipo y forma: Article (PostPrint)
Área (Departamento): Área Química Orgánica (Dpto. Química Orgánica)
You must give appropriate credit, provide a link to the license, and indicate if changes were made. You may do so in any reasonable manner, but not in any way that suggests the licensor endorses you or your use. You may not use the material for commercial purposes. If you remix, transform, or build upon the material, you must distribute your contributions under the same license as the original. Exportado de SIDERAL (2021-01-21-11:10:16)
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Record created 2016-07-12, last modified 2021-01-21