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Preparative enantiomeric separation of new selective CB 2 receptor agonists by liquid chromatography on polysaccharide‐based chiral stationary phases: Determination of enantiomeric purity and assignment of absolute stereochemistry by X‐ray structure analysis
Author(s) -
Stern Eric,
Goossens Laurence,
Retailleau Pascal,
Kauffmann Brice,
Bonte JeanPaul,
Depreux Patrick,
Goossens JeanFrancois
Publication year - 2011
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.20939
Subject(s) - chemistry , enantiomer , chromatography , enantiomeric excess , chirality (physics) , absolute configuration , chiral column chromatography , high performance liquid chromatography , repeatability , stereochemistry , organic chemistry , enantioselective synthesis , catalysis , nambu–jona lasinio model , chiral symmetry breaking , physics , quantum mechanics , quark
The development of high‐performance liquid chromatography (HPLC) methods using derivatized amylose chiral stationary phases has permitted preparative enantioseparations of substituted 4‐oxo‐1,4‐dihydroquinoline‐3‐carboxamide derivatives with satisfactory yields. These compounds constitute new potent selective agonists of the cannabinoid CB 2 receptor. Analytical enantioseparation methods using UV detection were validated to determine the enantiomeric purity of these compounds. Linear calibration curves in the range from 0.18 to 0.40 mM were obtained; repeatability, limits of detection (LOD), and quantification (LOQ) were determined: LOD varied, for the various solutes, from 0.5 to 1.2 μM. All the separated compounds were prepared with high enantiomeric purities superior to 99.3% Absolute configuration of the enantiomers was unequivocally established by single crystal X‐ray diffraction method and correlated to the chiroptical properties of isolated enantiomers. Chirality 2011. © 2011 Wiley‐Liss, Inc.