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Chiral separation of unmodified α‐hydroxy acids by ligand exchange HPLC using chiral copper(II) complexes of (S)‐phenylalaninamide as additives to the eluent
Author(s) -
Galaverna Gianni,
Pantò Francesco,
Dossena Arnaldo,
Marchelli Rosangela,
Bigi Franca
Publication year - 1995
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/chir.530070504
Subject(s) - chemistry , enantiomer , chromatography , high performance liquid chromatography , ligand (biochemistry) , chiral column chromatography , column chromatography , copper , chiral ligand , chirality (physics) , enantiomeric excess , enantioselective synthesis , organic chemistry , catalysis , chiral symmetry breaking , biochemistry , receptor , physics , quantum mechanics , quark , nambu–jona lasinio model
Copper(II) complexes of (S)‐phenylalaninamide have been successfully used for the direct enantiomeric separation of unmodified (R,S)‐α‐hydroxy acids in reversed phase high‐performance liquid chromatography (RP‐HPLC). The effect of various parameters (pH, eluent polarity, selector concentration) on enantioselectivity is discussed. Evidence is provided that a mechanism of ligand exchange is actually occurring during the chromatographic separation. The method is very convenient and easy to use, and the chiral selector is commercially available and can be recovered at the end of the analysis. A conventional achiral RP‐ODS‐2 column is used and no pretreatment of the samples is required. This method allows the accurate determination of the enantiomeric excess of α‐hydroxy acids in synthetic and biological samples. © 1995 Wiley‐Liss, Inc.