title: Descriptive structure-separation relationship studies in chiral ligand-exchange chromatography.
abstract: A new approach to model and interpret the separation of amino acid enantiomers is described. The descriptive structure-separation relationship (DSSR) study of a set of amino acid enantiomer couples analyzed with two chiral selectors S-benzyl-(R)-cysteine ((R)-SBC) and S-trityl-(R)-cysteine ((R)-STC) has been performed with the aim to highlight the molecular properties of the analyte affecting the enantiodiscrimination process. Although with some exceptions, the classification models obtained with (R)-STC indicate that the partial positive surface area (PPSA-1) is the suitable descriptor to account for the separation of both (R)- and (S)-enantiomers. On the other hand, two different descriptors characterize the separation process with (R)-SBC. While fractional negatively charged partial surface area (FNSA-3) results the discriminating descriptor for (R)-enantiomers, the relative polar surface area (RPSA) is able to best discriminate among (S)-enantiomers.
authors.affiliation: Dipartimento di Chimica e Tecnologia del Farmaco, Università degli Studi di Perugia, Perugia, Italy. natalini@chimfarm.unipg.it
authors.forename: Benedetto
authors.initials: B
authors.lastname: Natalini
authors.forename: Antonio
authors.initials: A
authors.lastname: Macchiarulo
authors.forename: Roccaldo
authors.initials: R
authors.lastname: Sardella
authors.forename: Alberto
authors.initials: A
authors.lastname: Massarotti
authors.forename: Roberto
authors.initials: R
authors.lastname: Pellicciari
mesh_terms: D000596:Amino Acids / Q000737:chemistry / Q000302:isolation & purification*; D002851:Chromatography, High Pressure Liquid / Q000379:methods*; D008024:Ligands; D008956:Models, Chemical; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D000596:Amino Acids; D008024:Ligands