Photophysics and Biological Applications of 7-Azaindole and Its Analogs

Abstract

7-Azaindole is the chromophoric moiety of 7-azatryptophan, which is an alternative to tryptophan as an optical probe of protein structure and dynamics. The great power of the 7-azaindole chromophore is that it is red shifted both in absorption and emission from tryptophan, that its fluorescence decay is single exponential in water under appropriate conditions, and that its emission is sensitive to solvent. In addition, 7-azatryptophan can be incorporated into synthetic peptides and bacterial protein. In this article, the interactions of 7-azaindole with its environment are discussed. Special attention is directed to the difference in its fluorescence properties in water as opposed to nonaqueous solvents. The sensitivity of 7-azaindole to its environment is demonstrated and then exploited by studying it and its analogs in peptides and in complexes with larger proteins containing many tryptophan residues.