The ability to equip oligonucleotides with additional chemical reactivity, such as click chemistry handles, or fluorescent properties has enabled many important biological discoveries. In particular, the Harki lab is interested in biomimetic nucleosides that can replace endogenous purines and pyrimidines in oligonucleotides and act as fluorescent reporters. We recently reported the nucleoside fluorophore 4-cyanoindole-2'-deoxyribonucleoside (<b>4CIN</b>), an isomorphic nucleoside analogue that minimally perturbs DNA stability and displays excellent fluorescence as a monomer (quantum yield, QY = 0.92) and in oligonucleotides (QY up to 0.31). Given the ease of indole synthesis and their suitability for development as fluorescent reporters, we investigated other indole nucleobases to yield a toolbox of indole fluorophores with a variety of properties, as well as novel click chemistry compatibility. This talk will discuss the synthesis, spectroscopic, and kinetic evaluation of new indole fluorophores and clickable analogues.

Indole nucleosides as a versatile scaffold for fluorophore development

2019 Fall National Meeting

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