Cationic acyclic cucurbit[n]uril-type containers: synthesis and molecular recognition toward nucleotides.

ABSTRACT: We report the synthesis of M2NH3 which is a tetracationic analogue of our prototypical acyclic CB[n]-type molecular container M2. Both M1NH3 and M2NH3 possess excellent solubility in D2O and do not undergo intermolecular self-association processes that would impinge on their molecular recognition properties. Compounds M1NH3 and M2NH3 do, however, undergo an intramolecular self-complexation process driven by ion-dipole interactions between the ureidyl C=O portals and the OCH2CH2NH3 arms along with inclusion of one aromatic wall in its own hydrophobic cavity. The Ka values for M1NH3 and M2NH3 toward seven nucleotides were determined by 1H NMR titration and found to be quite modest (Ka in the 102 - 103 M-1 range) although M2NH3 is slightly more potent. The more highly charged guests (e.g. ATP) form stronger complexes with M1NH3 and M2NH3 than the less highly charged guest (e.g. ADP, AMP). The work highlights the dominant influence of the ureidyl C=O portals on the molecular recognition behavior of acyclic CB[n]-type receptors and suggests routes (e.g. more highly charged arms) to enhance their recognition behavior toward anions.

SUBMITTER: Sigwalt D 

PROVIDER: S-EPMC5063241 | biostudies-other | 2016

REPOSITORIES: biostudies-other