56121 20210121114531.0 doi 10.1016/j.chroma.2015.02.055 sideral 89719 ART-2015-89719 eng (orcid)0000-0001-8105-2432 López-Ram-de-Víu, P. Universidad de Zaragoza High-performance liquid chromatographic enantioseparation of unusual amino acid derivatives with axial chirality on polysaccharide-based chiral stationary phases 2015 Access copy available to the general public Unrestricted 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]. info:eu-repo/grantAgreement/ES/DGA/GAE-102 info:eu-repo/semantics/openAccess by-nc-sa http://creativecommons.org/licenses/by-nc-sa/3.0/es/ 3.926 2015 CHEMISTRY, ANALYTICAL 11 / 75 = 0.147 2015 Q1 T1 BIOCHEMICAL RESEARCH METHODS 14 / 77 = 0.182 2015 Q1 T1 1.693 2015 Analytical Chemistry 2015 Q1 Organic Chemistry 2015 Q1 Medicine (miscellaneous) 2015 Q1 Biochemistry 2015 Q1 info:eu-repo/semantics/article info:eu-repo/semantics/acceptedVersion (orcid)0000-0002-4972-7476 Gálvez, J.A. Universidad de Zaragoza (orcid)0000-0001-9033-8459 Díaz-de-Villegas, M.D. 2013 765 Universidad de Zaragoza Dpto. Química Orgánica Área Química Orgánica 1390 (2015), 78-85 J. chromatogr. A Journal of Chromatography A 0021-9673 1029610 http://zaguan.unizar.es/record/56121/files/texto_completo.pdf Postprint 103783 http://zaguan.unizar.es/record/56121/files/texto_completo.jpg?subformat=icon icon Postprint oai:zaguan.unizar.es:56121 articulos driver 2021-01-21-11:10:16 ARTICLE