Chemical Biology Using Fluorinated Building Blocks

Abstract

There is a long and rich history of the use of fluorine‐containing molecules to modulate biological function. In recent years, incorporation of fluorine atoms into biomolecular assemblies has resulted in unprecedented control of structure and function. The electronegativity of fluorine has helped unveil the physical basis for the stability of collagen; incorporation of trifluoromethyl groups into peptides and proteins has resulted in hyperstable ensembles and enabled the control of oligomer formation in the nonpolar context of biological membranes. Further, fluorinated lipids segregate from hydrocarbon lipids with identical headgroups in bilayers and serve as better vehicles for transporting macromolecular cargo into living cells. Some select systems are highlighted here and the important role of fluorinated biomolecules is discussed.

A General Approach to Biocompatible Branched Fluorous Tags for Increased Solubility in Perfluorocarbon Solvents

“…This work coined the term “fluorous” and initiated the field of fluorous phase chemistry where perfluorinated tags were appended to organic compounds to facilitate purification by fluorous extraction. The use of fluorous tags has since been extended to biological applications to streamline proteomics, display bioactive molecules on microarrays, − improve transport into cells, , and encapsulate chromophores inside perfluorocarbon nanoemulsions. , …”