Synthesis and Tritium Labeling of New Aromatic Diazirine Building Blocks for Photoaffinity Labeling and Cross-Linking

Abstract

The synthesis of three bifunctional 3-phenyl-3-(trifluoromethyl)diazirinyl building blocks is described. These compounds were designed for their potential chemical reactivity toward a wide range of functional groups occurring in proteins and small molecules. Moreover, we also synthesized the tritiated versions of these three building blocks, using a recently reported chemoselective and regiospecific key-reaction. These building blocks represent a new family of radiolabeled molecules that can be utilized as photoactivatable tags for labeling of proteins or small molecules by using cross-linking or site-directed photoaffinity labeling techniques.