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Enantioselective Recognition of Chiral Guests by the Water-Soluble Chiral Keplerate {Mo132} Spherical Capsule with 30 Inner Lactate Ligands

preprint
submitted on 09.07.2019 and posted on 10.07.2019 by Nancy Watfa, Weimin Xuan, Zoe Sinclair, Robert Pow, Yousef Abul-Haija, De-Liang Long, Leroy Cronin
Investigations of chiral host guest chemistry are important to explore recognition in confined environments. Here, by synthesizing water-soluble chiral porous nanocapsule based on the inorganic metal-oxo Keplerate-type cluster, {Mo132} with chiral lactate ligands with the composition [Mo132O372(H2O)72(x-Lactate)30]42- (x = D or L), it was possible to study the interaction with a chiral guest, L/D-carnitine and (R/S)-2-butanol in aqueous solution. The enantioselective recognition was studied by quantitative 1H NMR and 1H DOSY NMR which highlighted that the chiral recognition is regulated by two distinct sites. Differences in the association constants (K) of L- and D-carnitine, which, due to their charge, are generally restricted from entering the interior of the host, are observed, indicating that their recognition predominantly occurs at the surface pores of the structure. Conversely, a larger difference in association constants (KS/KR = 3) is observed for recognition within the capsule interior of (R)- and (S)-2-butanol.

Funding

EPSRC and ERC

History

Email Address of Submitting Author

lee.cronin@glasgow.ac.uk

Institution

University of Glasgow

Country

United Kingdom

ORCID For Submitting Author

0000-0001-8035-5757

Declaration of Conflict of Interest

No conflict of interests

Exports