Synthesis and evaluation of a new biselector s‐triazine based chiral stationary phase for enantioselective HPLC: potentiality of the approach and perspectives

Abstract

A s-triazine scaffold bearing a free and a protected amino group was used for connecting two different chiral auxiliaries, whose enantiodiscriminating capabilities in enantioselective chromatography are well documented. A biselector system was synthesized and, after linkage to silica gel, used for the chromatographic resolution of different racemic analytes, chosen among the compounds resolved by the two different isolated chiral auxiliaries. The obtained chromatographic results were compared with literature data related to the use of the two chiral stationary phases (CSPs) whose chiral moieties constitute the biselector CSP, allowing us to gain useful information about potentialities and limitations of this approach for obtaining independent CSPs having broader applicability with respect to the classical independent monoselector CSPs.

Supramolecular Chiro-Biomedical Assays and Enantioselective HPLC Analyses for Evaluation of Profens as Non-Steroidal Anti-Inflammatory Drugs, Potential Anticancer Agents and Common Xenobiotics

“…Lecci and Iuliano [112] focused their efforts to synthesize the biselector CSPs, where end-used chiral selector possesses the structural features of two different chiral auxiliaries which normally act as the specific stereoselectors towards different classes of racemic compounds. In biselector (or bimodal) CSP the two connected dissimilar chiral auxiliaries did not act independently of one another but behaved differently as far as the extent of enantioselectivity and enantiorecognition mechanism driven by set of supramolecular forces of each of them were concerned.…”