Hydrophilic Oligo(lactic acid)s Captured by a Hydrophobic Polyaromatic Cavity in Water

被引：39

作者：

Kusaba, Shunsuke ^{[1
]}

Yamashina, Masahiro ^{[1
]}

Akita, Munetaka ^{[1
]}

Kikuchi, Takashi ^{[2
]}

Yoshizawa, Michito ^{[1
]}

机构：

[1] Tokyo Inst Technol, Lab Chem & Life Sci, Inst Innovat Res, Midori Ku, 4259 Nagatsuta, Yokohama, Kanagawa 2268503, Japan

[2] Rigaku Corp, 3-9-12 Matsubaracho, Akishima, Tokyo 1968666, Japan

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2018年 / 57卷 / 14期

关键词：

CH-; interactions; coordination capsules; hydrogen bonds; oligo(lactic acid)s; water; M2L4 MOLECULAR CAPSULE; HIGH-ENERGY WATER; POLY(LACTIC ACID); RECOGNITION; DEGRADATION; COMPLEXES; BINDING; GUESTS; ENCAPSULATION;

D O I：

10.1002/anie.201800432

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

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=3x10(5)m(-1)). X-ray crystallographic and ITC analyses revealed that the unusual host-guest behavior is caused by enthalpic stabilization through multiple CH- 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.

引用

页码：3706 / 3710

页数：5

共 45 条

[1]

[Anonymous], 2016, ANGEW CHEM

[2]

August D. P., 2016, ANGEW CHEM, V128, P15246

[3] Maximizing Coordination Capsule-Guest Polar Interactions in Apolar Solvents Reveals Significant Binding [J].