Cysteine-based chiral selectors for the ligand-exchange separation of amino acids.
Three cysteine-based coated selectors, S-benzyl-(R)-cysteine, S-diphenylmethyl-(R)-cysteine and S-trityl-(R)-cysteine, have been used in the ligand-exchange separation of a selected set of natural and unnatural underivatized amino acids. With only few exceptions, a gain in enantiodiscrimination was obtained when the most lipophilic discriminating agent, characterized by the presence of a trityl moiety, was engaged. Moreover, a new descriptive structure-separation relationship study through molecular surface (Jurs) and shape (Shadow) descriptors provided evidence that specific physico-chemical features of the employed chiral selector result decisive in establishing which property of the analyte is responsible for the enantiorecognition accomplishment.
Natalini
Benedetto
B
Dipartimento di Chimica e Tecnologia del Farmaco, Università degli Studi di Perugia, Via del Liceo 1, 06123 Perugia, Italy. natalini@chimfarm.unipg.it
Sardella
Roccaldo
R
Macchiarulo
Antonio
A
Pellicciari
Roberto
R
D000596:Amino Acids / Q000302:isolation & purification*; D005591:Chemical Fractionation / Q000379:methods; D002851:Chromatography, High Pressure Liquid / Q000295:instrumentation / Q000379:methods*; D003545:Cysteine / Q000031:analogs & derivatives* / Q000737:chemistry; D008024:Ligands; D015203:Reproducibility of Results; D013237:Stereoisomerism
D000596:Amino Acids; D008024:Ligands; D003545:Cysteine