Cargando…

A polyaromatic nanocapsule as a sucrose receptor in water

Selective recognition of saccharides by artificial receptors in water is a challenging goal due to their strong hydrophilicities and complex molecular structures with subtle regio- and stereochemical differences. We report the selective and efficient encapsulation of d-sucrose within a coordination-...

Descripción completa

Detalles Bibliográficos
Autores principales: Yamashina, Masahiro, Akita, Munetaka, Hasegawa, Taisuke, Hayashi, Shigehiko, Yoshizawa, Michito
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Association for the Advancement of Science 2017
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5573335/
https://www.ncbi.nlm.nih.gov/pubmed/28875169
http://dx.doi.org/10.1126/sciadv.1701126
Descripción
Sumario:Selective recognition of saccharides by artificial receptors in water is a challenging goal due to their strong hydrophilicities and complex molecular structures with subtle regio- and stereochemical differences. We report the selective and efficient encapsulation of d-sucrose within a coordination-driven molecular capsule from natural saccharide mixtures in water (~100% selectivity, >85% yield, and ~10(3) M(−1) binding constant). Unlike previous artificial receptors and natural receptors that rely on multiple hydrogen-bonding interactions, theoretical calculations and control experiments indicate that the observed unique selectivity arises from multiple CH-π interactions between the sucrose hydrocarbon backbone and the shape-complementary polyaromatic cavity (~1 nm in diameter) of the capsule.