In this work the simultaneous separation of chiral active pharmaceutical ingredients (API) in salt form from their counterions has been performed by using different high-efficiency macrocyclic glycopeptide-based chiral stationary phases (CSPs). Not only a new zwitterionic vancomycin-based CSP has been prepared (similarly to what was done for teicoplanin) but macrocyclic selectors have also been bonded to sub-2 μm fully porous silica particles through traditional ureidic linkage to obtain versions of CSPs suitable for ultra-high performance applications. The direct separation of chiral APIs and counterions is particularly attracting since it simplifies the workflow traditionally used with reduction of analysis time and costs. The wide selection of macrocyclic antibiotics CSPs now available has allowed to manage different cases that can happen in the simultaneous separation of APIs and their counterions (either cations or anions). Indeed, while inorganic cations are retained on traditional vancomycin- and teicoplanin-based CSPs, inorganic anions are almost unretained (due to Donnan's effect). On the other hand, cations and anions can be both retained on the zwitterionic versions of these CSPs. Afterwards, zwitterionic CSPs allowed the separation of other compounds including N-derivative amino-acids, profens, polyols, sugar anomers, oligosaccharides and inorganic anions/cations opening new perspectives in the use of this family of CSPs.

Direct analysis of chiral active pharmaceutical ingredients and their counterions by ultra high performance liquid chromatography with macrocyclic glycopeptide-based chiral stationary phases

Ismail, Omar H.;Catani, Martina;Cavazzini, Alberto;Gasparrini, Francesco
2018

Abstract

In this work the simultaneous separation of chiral active pharmaceutical ingredients (API) in salt form from their counterions has been performed by using different high-efficiency macrocyclic glycopeptide-based chiral stationary phases (CSPs). Not only a new zwitterionic vancomycin-based CSP has been prepared (similarly to what was done for teicoplanin) but macrocyclic selectors have also been bonded to sub-2 μm fully porous silica particles through traditional ureidic linkage to obtain versions of CSPs suitable for ultra-high performance applications. The direct separation of chiral APIs and counterions is particularly attracting since it simplifies the workflow traditionally used with reduction of analysis time and costs. The wide selection of macrocyclic antibiotics CSPs now available has allowed to manage different cases that can happen in the simultaneous separation of APIs and their counterions (either cations or anions). Indeed, while inorganic cations are retained on traditional vancomycin- and teicoplanin-based CSPs, inorganic anions are almost unretained (due to Donnan's effect). On the other hand, cations and anions can be both retained on the zwitterionic versions of these CSPs. Afterwards, zwitterionic CSPs allowed the separation of other compounds including N-derivative amino-acids, profens, polyols, sugar anomers, oligosaccharides and inorganic anions/cations opening new perspectives in the use of this family of CSPs.
Ismail, Omar H.; Antonelli, Michela; Ciogli, Alessia; De Martino, Michela; Catani, Martina; Villani, Claudio; Cavazzini, Alberto; Ye, Michael; Bell, David S.; Gasparrini, Francesco
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