Chiral bambusurils for enantioselective recognition of chiral carboxylate anions


                                  Jan Sokolov, Vladimír Šindelář*
                                                 ^

 Department of Chemistry and RECETOX, Faculty of Science, Masaryk University Kamenice 5, Brno, 625
                                              00 Brno

                                   e-mail: sokolov@mail.muni.cz


Bambusurils are macrocyclic compounds that can bind anions with high affinity and selectivity.^1
Bambusurils reported until recently are achiral molecules, which were used for binding achiral
anionic guests. Hereby we report synthesis of two novel chiral bambusuril macrocycles.^2 These
macrocycles are obtained by condensation of enantiomerically pure chiral glycolurils with
paraformaldehyde on gram scale without any chromatographic purification. Chiral bambusurils bind
chiral carboxylate anions including amino acids and drug molecules with enantioselectivity ranging
from 1.1 to 3.2.


Figure 1. Structure of chiral bambusurils.



This work was supported Czech Science Foundation (18-21801S) and by RECETOX Research Infrastructure
(LM2015051 and CZ.02.1.01/0.0/0.0/16_013/0001761). Jan Sokolov acknowledges Brno Ph.D. Talent
Scholarship programme funded by the Brno City Municipality


 1. Lízal, T.; Šindelář, V.; Isr. J. Chem.  2017, 58, 326.


 2. Sokolov, J.; Šindelář, V.; Chem Eur. J.  2018, 24, 15482.