Campus Units

Chemistry

Document Type

Article

Publication Version

Published Version

Publication Date

2015

Journal or Book Title

Journal of the American Chemical Society

Volume

137

Issue

2

First Page

843

Last Page

849

DOI

10.1021/ja510823h

Abstract

When disengaged interactions within a receptor are turned on by its guest, these intrahost interactions will contribute to the overall binding energy. Although such receptors are common in biology, their synthetic mimics are rare and difficult to design. By engineering conflictory requirements between intrareceptor electrostatic and hydrophobic interactions, we enabled complementary guests to eliminate the “electrostatic frustration” within the host and turn on the intrahost interactions. The result was a binding constant of Ka >105 M–1 from ammonium–carboxylate salt bridges that typically function poorly in water. These cooperatively enhanced receptors displayed excellent selectivity in binding, despite a large degree of conformational flexibility in the structure.

Comments

Reprinted (adapted) with permission from Journal of the American Chemical Society 137 (2015): 843, doi:10.1021/ja510823h. Copyright 2015 American Chemical Society.

Copyright Owner

American Chemical Society

Language

en

File Format

application/pdf

Included in

Chemistry Commons

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