Chiral Nafion membranes prepared by strong electrostatic binding of multiply positively charged β-cyclodextrin derivatives for tryptophan racemic mixtures’ separation.

0541140 - ÚCHP 2022 RIV NL eng J - Journal Article
Kasal, P. - Michel, Marine - Gaálová, Jana - Cuřínová, Petra - Izák, Pavel - Jindřich, J.
Chiral Nafion membranes prepared by strong electrostatic binding of multiply positively charged β-cyclodextrin derivatives for tryptophan racemic mixtures’ separation.
Materials Today Communications. Roč. 27, JUN 2021 (2021), č. článku 102234. ISSN 2352-4928. E-ISSN 2352-4928
R&D Projects: GA ČR(CZ) GA20-09980S; GA MPO FV10082
Institutional support: RVO:67985858
Keywords : optical resolution * cyclodextrins * racemic mixtures
OECD category: Chemical process engineering
Impact factor: 3.662, year: 2021
Method of publishing: Open access with time embargo

Three multiply positively charged β-cyclodextrin derivatives were prepared and ionically bound to a Nafion® 117 membrane. The derivatives differed only in the length of the linker, which connects the positively charged anchor to the cyclodextrin moiety. The resulting membranes exert preferential sorption of l-enantiomer of tryptophan from its racemic mixture (ee reaching 44 % for the medium linker length). The membrane follows the retarded transport mechanism. Using a fluorophore-tagged cyclodextrin modifier, we confirmed no leaching of the modifier from the membrane. Thus, we proved the potential of the approach of electrostatic binding of chiral selectors for the enantioseparation of chiral drugs.
Permanent Link: http://hdl.handle.net/11104/0318741