title: S-trityl-(R)-cysteine, a multipurpose chiral selector for ligand-exchange liquid chromatography applications.
abstract: The stratification of 0.040-0.050 g of S-trityl-(R)-cysteine ((R)-STC) onto a conventional ODS phase produces a very effective (α and RS up to 5.71 and 12.09, respectively) and stable (more than 30 days of repeated analysis) chiral ligand-exchange chromatography (CLEC) coated chiral stationary phase (C-CSP). With a few specific exceptions, a (R) < (S) enantiomer elution order can be easily predicted. The (R)-STC-based C-CSP can be successfully exploited also at a preparative level for enantioisolations of CNS active amino acids (AAs), with a racemate loadability up to 0.015 g for single injection. The CLEC (R)-STC-based system can be helpful in monitoring the presence of (R)-AAs in edible products and other organic materials, thus contributing to evaluating product quality and diagnosing subclinical pathological states in animals and humans. Very profitably, molecular modeling-based computer-assisted classification analyses can reveal the actual enantioseparation ability of the (R)-STC phase towards a specific compound.
authors.affiliation: a Department of Pharmaceutical Sciences , University of Perugia , Perugia , Italy.
authors.forename: Roccaldo
authors.initials: R
authors.lastname: Sardella
authors.forename: Federica
authors.initials: F
authors.lastname: Ianni
authors.forename: Antonella
authors.initials: A
authors.lastname: Lisanti
authors.forename: Stefania
authors.initials: S
authors.lastname: Scorzoni
authors.forename: Maura
authors.initials: M
authors.lastname: Marinozzi
authors.forename: Benedetto
authors.initials: B
authors.lastname: Natalini
mesh_terms: D000818:Animals; D002851:Chromatography, High Pressure Liquid / Q000379:methods*; D002852:Chromatography, Ion Exchange / Q000379:methods*; D003545:Cysteine / Q000031:analogs & derivatives* / Q000737:chemistry; D006801:Humans; D008024:Ligands; D008958:Models, Molecular; D013237:Stereoisomerism
chemical_list: D008024:Ligands; C003724:3-tritylthio-L-alanine; D003545:Cysteine
keywords: chiral ligand-exchange chromatography; coated-chiral stationary phase; diagnostic tool; enantiorecognition mechanism; food analysis; liquid-chromatography; preparative-scale enantioresolution