Highly selective chiral recognition on polymer supports: preparation of a combinatorial library of dihydropyrimidines and its screening for novel chiral HPLC ligands

Chiral separation by chromatographic and electromigration techniques. A Review

“…Following the chiral reciprocity principle, Lewandowski et al [68] found among a library of 140 synthesized 4-aryl-1,4-dihydropyrimidines a candidate which was used for the preparation of a polymeric CSP for the chiral separation of N-3,5-dinitrobenzoyl leucine. To find a suitable selector for N-2,5-dinitrobenzoylated amino acid derivatives, the same group attached a library of 36 different amino acid anilides to polymer beads which were used as an HPLC CSP [69].…”

Determination of absolute configuration in 4-aryl-3,4-dihydro-2(1H)-pyrimidones by high performance liquid chromatography and CD spectroscopy

“…In the past, optically pure DHPMs were obtained by resolution of the corresponding racemic carboxylic acids via diastereomeric ammonium salts, 8 by separation of diastereomeric derivatives bearing chiral auxiliaries at N(3), [3][4][5] or by enantioselective HPLC. 9,10 In each case, the absolute configuration of the enantiomerically pure material had to be determined by single-crystal X-ray analysis of suitable diastereomeric derivatives. [3][4][5]8 In recent years, the combined use of enantioselective chromatographic separation techniques with chiroptical spectroscopic methods has been developed in order to determine the absolute configuration of chiral molecules.…”

Peptide and peptidomimetic chiral selectors in liquid chromatography

“…If a racemic library member can be resolved efficiently by this chiral analyte stationary phase, then a stationary phase immobilized with one enantiomer of this library member is likely to be able to resolve the racemic target analyte efficiently, according to the reciprocal principle of chromatography. This approach was initially proven using a library of racemic dihydropyrimidines [12] and then applied to a peptidomimetic library prepared by Ugi multicomponent condensation [14]. Ugi condensation has been used extensively for the synthesis of drug-like molecules with a peptide core structure.…”

“…A reciprocal approach to screen racemic libraries including peptide and peptide mimetics libraries was investigated [12,13]. In this method, one enantiomer of the analyte to be resolved is first immobilized onto a chromatographic support as a chiral analyte stationary phase.…”