Synthesis of the chiral stationary phase based on functionalized ZIF-8 with amylose carbamate
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Synthesis of the chiral stationary phase based on functionalized ZIF-8 with amylose carbamate Tamires Menezes1,2, Kátilla Santos1,2, Elton Franceschi1,2, Gustavo Borges1,2, Cláudio Dariva1,2, Silvia Egues1,2, Juliana De Conto1,a) , Cesar Santana1,2 1 Center for Studies on Colloidal Systems (NUESC)/Institute of Technology and Research (ITP), Av. Murilo Dantas, 300, Aracaju, CEP 49032-490, Sergipe, Brazil 2 Tiradentes University (UNIT), Postgraduate Programme in Process Engineering (PEP), Av. Murilo Dantas, 300, Aracaju, CEP 49032-490, Sergipe, Brazil a) Address all correspondence to this author. e-mail: [email protected]
Received: 15 June 2020; accepted: 14 September 2020
Commercial chiral stationary phases (CSPs) are based mainly on polysaccharides supported on silica; however, the pharmaceutical industry shows a special interest on chiral separations, exhibiting high financial investment in the development of new CSPs. These can be structured by a new optically active compound or different support. Thus, metal–organic frameworks (MOFs) are crystalline materials that arise with great potential for support, due to its high porosity, the strong intermolecular force between the metal and the ligand selectivity, and high adsorption capacity. Interested in this, this work proposes a new CSP using the metal–organic structure ZIF-8 (Basolite Z1200) due to its high mechanical stability. To this end, it is proposed the modification of the ZIF-8 with the optically active compound, tris-3,5-dimethylphenylcarbamate amylose. Through characterization textural, structural, and physicochemical performed, it is possible to confirm the synthesis of the chiral compound (amylose carbamate), as well as the functionalization of the metal–organic structure with tris-3,5dimethylphenylcarbamate amylose (ZIF-8-PEI-CA). In addition, as a validation technique, HPLC can detect the presence of enantiomers present in the racemic mixture of Troger bases.
Introduction In the 1960s, the commercialization of thalidomide drew attention to the importance of recognizing chirality in drugs because of the growing worldwide reports of phocomelia, an anomaly caused by one of the thalidomide enantiomers that causes malformation in fetuses. From that moment on, regulatory agencies have pushed pharmaceutical industry toward the recognition, separation, and contribution for the use of enantiomers suggested for commercialization [1]. Therefore, the pharmaceutical industry has shown in recent years a significant interest in studies of new chiral stationary phases (CSPs) in order to obtain greater selectivity. During the preliminary testing phase of new chiral drugs, chromatography allowed quick access to pure enantiomers and can advantageously replace the often-prolonged elaboration of an enantioselective synthesis [2]. The review by Okamoto and Yashima [3] is an important milestone on the direct separation of enantiomers performed in stationary polysaccharide phases on silica, which nowadays
are among the most popular CSPs. In particular, cellulose and amyl
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