Amino acids as chiral auxiliaries in cyanuric chloride‐based chiral derivatizing agents for enantioseparation by liquid chromatography

Abstract

This review summarizes and critically evaluates the recent research on application of amino acids and amino acid amides as chiral auxiliaries in cyanuric chloride (CC) based chiral derivatizing agents (CDRs), used in the indirect approach for enantiomeric resolution. Methods of synthesis of such CDRs, methods for synthesis of diastereomers of a variety of racemic compounds and parameters of liquid chromatographic separation, along with their prospects and their limitations in indirect enantioresolution, are discussed. Application of the said CDR(s) and the technical approach to be used that are discussed should be beneficial for control of enantiomeric purity in pharmaceutical industry, verification of enantiomeric ratio of commercial formulations and the development of methods for indirect resolution of a variety of chiral compounds. Derivatization methods are particularly required when a chromophore is to be introduced in low UV absorbing molecules, for their detection.

Bioassay, determination and separation of enantiomers of atenolol by direct and indirect approaches using liquid chromatography: A review

“…The literature reveals that a variety of CDRs have been used for enantioseparation of ( RS )‐Atl. These include CDRs based on: difluoro dinitro benzene (DFDNB) (Bhushan & Tanwar, , , ); cyanuric chloride (CC) (Batra & Bhushan, ; Bhushan & Dixit, ); isothiocyanates (Li, Yao, & Zeng, ; Péter, Gyéresi, & Fülöp, ); esters or anhydrides of carboxylic acids (Bhushan & Tanwar, ; Michael, Kevin, & Thomas, ; Rosseel et al, ); ( S )‐naproxen (Bhushan & Tanwar, ; Singh & Bhushan, ). …”

Rapid and efficient one‐step purification of a serralysin family protease by using a p‐aminobenzamidine‐modified affinity medium

“…The benzamine derivative p ‐aminobenzamidine (pABA) was chosen as affinity ligand for our purposes taking into account that it is commercially available and has a favorable configuration for synthesis affinity media. The cyanuric chloride, a typical cyclic compound, was used as spacer arm to immobilize the affinity ligand to activated Sepharose 6B beads, thus supplying a higher mechanical strength for the ligand stabilization . The experimental approach used for the synthesis of pABA‐modified Sepharose 6B is schematically reported in Fig.…”

Methods and approaches for determination and enantioseparation of (RS)‐propranolol

“…appropriately (Blotny, ). Batra and Bhushan () critically evaluated application of CC‐based CDRs (containing amino acids and amino acid amides as chiral auxiliaries) for enantiomeric resolution of a variety of racaemic compounds covering methods of synthesis of such CDRs, and diastereomeric derivatives (of a variety of pharmaceutically important compounds including certain β ‐adrenolytics) along with parameters of liquid chromatographic separation.…”