Synthesis of Diazirinyl Photophore and Optically Pure Diazirinylphenylalanines for Photoaffinity Labeling

Abstract

As photophores in photoaffinity labeling, three major types, arylazide, benzophenone, and diazirine have been used and contributed to the understanding of molecular biology processes. In particular, diazrine is a significantly useful photophore because it has some advantages such as its relatively small size, stability, low rate of rearrangement, and generating a high reactive carbene with longer wavelength which reduces damage to the target molecules. Nevertheless, despite these many advantages in diazirine, there are reports in which arylazide and benzophenone are generally utilized for photoaffinity labeling compared with diazirine due to its synthetic difficulty onto ligands. To overcome this problem, recently many researchers have addressed to establish the efficient synthetic route of diazirinyl compounds. Particularly, α-aromatic amino acids possess not only biological activities themselves but also basic component of protein (bioactive peptide). In addition, a number of heterocyclic bioactive compounds have variety of attractive biological activities. Therefore, their diazirinyl compounds promise the molecular biology processes. In this chapter, firstly, it is demonstrated the simple and efficient preparation of diazirine on aromatics and aliphatic chains. Furthermore post-functional derivatization of them is also described to diversify bioactive compounds.