Abstract:
:Copper(II) complexes of N2-octyl-(S)-phenylalaninamide (Noc-Phe-NH2), N2-dodecyl-(S)-phenylalaninamide (Ndo-Phe-NH2), and N2-octyl-(S)-norleucinamide (Noc-NLeu-NH2), dynamically adsorbed on a reversed-phase C18 column, were able to perform the direct enantiomeric separation of unmodified amino acids, amino acid amides and esters, hydroxy acids, and dipeptides by elution with aqueous or mixed aqueous-organic solutions containing copper(II) sulphate or acetate. The role played by several parameters in the separation procedure was examined with the copper(II) complex of Noc-Phe-NH2 [concentration of the copper(II) ion in the eluent, pH and eluent polarity, amount of adsorbed selector]. The separation was shown to occur entirely on the stationary phase. The mechanism of chiral discrimination is discussed in terms of the chromatographic parameters and of the structure of the copper(II) complexes in solution and in the solid state. The chiral stationary phase maintained its separation ability for about 3 months. However, the column could be easily restored by recovering the selector with methanol and repeating the loading procedure.
journal_name
Chiralityjournal_title
Chiralityauthors
Galaverna G,Corradini R,Dossena A,Marchelli R,Dallavalle Fdoi
10.1002/(SICI)1520-636X(1996)8:2<189::AID-CHIR3>3.subject
Has Abstractpub_date
1996-01-01 00:00:00pages
189-96issue
2eissn
0899-0042issn
1520-636Xpii
10.1002/(SICI)1520-636X(1996)8:2<189::AID-CHIR3>3.journal_volume
8pub_type
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