Issue 2, 2021

Biomimetic hydrogen-bonding cascade for chemical activation: telling a nucleophile from a base

Abstract

Hydrogen bonding-assisted polarization is an effective strategy to promote bond-making and bond-breaking chemical reactions. Taking inspiration from the catalytic triad of serine protease active sites, we have devised a conformationally well-defined benzimidazole platform that can be systematically functionalized to install multiple hydrogen bonding donor (HBD) and acceptor (HBA) pairs in a serial fashion. We found that an increasing number of interdependent and mutually reinforcing HBD–HBA contacts facilitate the bond-forming reaction of a fluorescence-quenching aldehyde group with the cyanide ion, while suppressing the undesired Brønsted acid–base reaction. The most advanced system, evolved through iterative rule-finding studies, reacts rapidly and selectively with CN to produce a large (>180-fold) enhancement in the fluorescence intensity at λmax = 450 nm.

Graphical abstract: Biomimetic hydrogen-bonding cascade for chemical activation: telling a nucleophile from a base

Supplementary files

Article information

Article type
Edge Article
Submitted
12 9 2020
Accepted
01 11 2020
First published
02 11 2020
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY-NC license

Chem. Sci., 2021,12, 590-598

Biomimetic hydrogen-bonding cascade for chemical activation: telling a nucleophile from a base

H. Park and D. Lee, Chem. Sci., 2021, 12, 590 DOI: 10.1039/D0SC05067A

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