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Copper(II) complexes of N 2 ‐alkyl‐(S)‐amino acid amides as chiral selectors for dynamically coated chiral stationary phases in RP‐HPLC
Author(s) -
Galaverna G.,
Corradini R.,
Dossena A.,
Marchelli R.,
Dallavalle F.
Publication year - 1996
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/(sici)1520-636x(1996)8:2<189::aid-chir3>3.0.co;2-e
Subject(s) - chemistry , alkyl , chiral stationary phase , high performance liquid chromatography , chiral column chromatography , copper , chiral derivatizing agent , chromatography , organic chemistry , amino acid , combinatorial chemistry , biochemistry
Copper(II) complexes of N 2 ‐octyl‐(S)‐phenylalaninamide (Noc‐Phe‐NH 2 ), N 2 ‐dodecyl‐(S)‐phenylalaninamide (Ndo‐Phe‐NH 2 ), and N 2 ‐octyl‐(S)‐norleucinamide (Noc‐NLeu‐NH 2 ), dynamically adsorbed on a reversed‐phase C 18 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‐NH 2 [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. © 1996 Wiley‐Liss, Inc.