Use of an o-Benzyl-(S)-Serine Containing Eluent for the Efficient Ligand-Exchange Chromatography-Based Enantioseparation of Constrained Glutamate Receptor Ligands

Four dihydroisoxazole prolines and four dihydroisoxazole cyclopentane derivatives were submitted to chiral ligand-exchange chromatographic analysis in the presence of O-benzyl-(S)-serine, as the chiral mobile phase additive to the eluent. The 1.0 mM O-benzyl-(S)-serine and 0.5 mM Cu(NO 3 ) 2 eluent...

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Bibliographic Details
Published in:Analytical letters 2015-02, Vol.48 (3), p.383-395
Main Authors: Ianni, Federica, Sardella, Roccaldo, Lisanti, Antonella, Giacchè, Nicola, Conti, Paola, Pinto, Andrea, Tamborini, Lucia, Natalini, Benedetto
Format: Article
Language:English
Subjects:
Chiral ligand-exchange chromatography
Chiral mobile phase additive
Chromatography
Derivatives
Dihydroisoxazole amino acid derivatives
Eluents
Elution
Ligands
Mathematical analysis
O-benzyl-(s)-serine
Receptors
Spectroscopy
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Summary:Four dihydroisoxazole prolines and four dihydroisoxazole cyclopentane derivatives were submitted to chiral ligand-exchange chromatographic analysis in the presence of O-benzyl-(S)-serine, as the chiral mobile phase additive to the eluent. The 1.0 mM O-benzyl-(S)-serine and 0.5 mM Cu(NO 3 ) 2 eluent flowed at 1.0 mL/min through a conventional octadecylsilica-based stationary phase maintained at 25°C and provided excellent levels of enantioselectivity and resolution for all the species. By using enantiomers as model compounds, the method was validated revealing that the mixed ternary diastereomeric eluates present slightly different spectroscopic properties. The selected chiral ligand-exchange chromatography method was applied for semi-preparative enantioisolation that allowed the establishment of the k(−) 
ISSN:0003-2719
1532-236X
DOI:10.1080/00032719.2014.946040