Fluorescent nucleosides are immensely useful chemical tools in biochemical research. These compounds are frequently incorporated into nucleic acids for a variety of applications. The most widely utilized fluorescent nucleoside is 2-aminopurine-2′-deoxyribonucleoside (2APN). However, 2APN is limited by a moderate Stokes shift and quantum yield. We recently reported 4-cyanoindole-2′-deoxyribonucleoside (4CIN), which offers a larger Stokes shift and superior quantum yield in comparison to 2APN. To further improve upon 4CIN, we combined the structural features present in 2APN and 4CIN and synthesized a small library of additional analogues. The biophysical properties of these new compounds were measured including UV absorbance and fluorescence, molar extinction coefficient, quantum yield, and fluorescence lifetime. This poster will present our efforts to synthesize and biophysically characterize these novel fluorescent nucleosides, which will serve as valuable chemical tools in nucleic acid applications.

Synthesis and biophysical characterization of fluorescent indole nucleoside analogues

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ACS Fall 2022

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