From small changes to big gains: pyridinium-based tetralactam macrocycle for enhanced sugar recognition in water.

ABSTRACT: The complex distribution of functional groups in carbohydrates, coupled with their strong solvation in water, makes them challenging targets for synthetic receptors. Despite extensive research into various molecular frameworks, most synthetic carbohydrate receptors have exhibited low affinities, and their interactions with sugars in aqueous environments remain poorly understood. In this work, we present a simple pyridinium-based hydrogen-bonding receptor derived from a subtle structural modification of a well-known tetralactam macrocycle. This small structural change resulted in a dramatic enhancement of glucose binding affinity, increasing from 56 M^-1 to 3001 M^-1. Remarkably, the performance of our synthetic lectin surpasses that of the natural lectin, concanavalin A

SUBMITTER: Zhai C 

PROVIDER: S-EPMC11575561 | biostudies-literature | 2024 Nov

REPOSITORIES: biostudies-literature