Preparation of PSEBS membranes bearing (S)-(−)-methylbenzylamine as chiral selector

0518380 - ÚMCH 2021 RIV GB eng J - Journal Article
Otmar, Miroslav - Gaálová, Jana - Žitka, Jan - Brožová, Libuše - Cuřínová, Petra - Kohout, M. - Hovorka, Š. - Bara, J. E. - Van der Bruggen, B. - Jirsák, J. - Izák, Pavel
Preparation of PSEBS membranes bearing (S)-(−)-methylbenzylamine as chiral selector.
European Polymer Journal. Roč. 122, 5 January (2020), s. 1-6, č. článku 109381. ISSN 0014-3057. E-ISSN 1873-1945
R&D Projects: GA ČR(CZ) GA17-00089S
Institutional support: RVO:61389013 ; RVO:67985858
Keywords : optical resolution * racemic mixture * membrane technology
OECD category: Chemical process engineering; Chemical process engineering (UCHP-M)
Impact factor: 4.598, year: 2020
Method of publishing: Limited access
https://www.sciencedirect.com/science/article/pii/S0014305719311930?via%3Dihub

Nowadays, there is a strong need for replacement of racemates by enantiomerically pure drugs. Enantioseparation on polymer membranes seems to be one of the promising and economically feasible technologies for this purpose. As a material for membrane construction, linear polymer molecules bearing covalently bonded chiral selectors are very promising according to recent reports. A membrane formed from chloromethylated polystyrene-block-poly(ethylene-ran-butylene)-block-polystyrene (PSEBS) was cast and subsequently functionalized with a chiral selector (S)-(−)-α-methylbenzylamine. In preferential sorption experiments with racemic tryptophan and ibuprofen, the prepared membrane exhibited a higher affinity to l-tryptophan and (R)-(−)-ibuprofen than to corresponding enantiomers. The significant change in peak ratio from 48:52 to 60:40 (d-tryptophan:l-tryptophan) was observed. This indicates the high potential of the covalently bonded (S)-(−)-α-methylbenzylamine selector for the fabrication of membranes selective towards chiral acids and ampholytes.
Permanent Link: http://hdl.handle.net/11104/0304003