Combining Click Reactions for the One-Pot Synthesis of Modular Biomolecule Mimetics

Org Lett. 2019 Sep 20;21(18):7544-7548. doi: 10.1021/acs.orglett.9b02811. Epub 2019 Sep 10.

Abstract

Here, we report on the first combined one-pot use of the two so-called "click reactions": the thiol-ene coupling and the copper-catalyzed alkyne-azide cycloaddition. These reactions were employed in an alternating and one-pot fashion to combine appropriately functionalized monomeric carbohydrate building blocks to create mimics of trisaccharides and tetrasaccharides as single anomers, with only minimal purification necessary. The deprotected oligosaccharide mimics were found to bind both plant lectins and human galectin-3.

Publication types

  • Research Support, Non-U.S. Gov't