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Hydrophilic Oligo(lactic acid)s Captured by a Hydrophobic Polyaromatic Cavity in Water
Author(s) -
Kusaba Shunsuke,
Yamashina Masahiro,
Akita Munetaka,
Kikuchi Takashi,
Yoshizawa Michito
Publication year - 2018
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201800432
Subject(s) - lactic acid , chemistry , hydrogen bond , hydrophobic effect , molecule , polymer chemistry , chemical engineering , organic chemistry , bacteria , genetics , biology , engineering
Biologically relevant hydrophilic molecules rarely interact with hydrophobic compounds and surfaces in water owing to effective hydration. Nevertheless, herein we report that the hydrophobic cavity of a polyaromatic capsule, formed through coordination‐driven self‐assembly, can encapsulate hydrophilic oligo(lactic acid)s in water with relatively high binding constants (up to K a =3×10 5 m −1 ). X‐ray crystallographic and ITC analyses revealed that the unusual host–guest behavior is caused by enthalpic stabilization through multiple CH–π and hydrogen‐bonding interactions. The polyaromatic cavity stabilizes hydrolyzable cyclic di(lactic acid) and captures tetra(lactic acid) preferentially from a mixture of oligo(lactic acid)s even in water.