<br/><br/>Small fluorescent nucleoside analogues (FNAs) are already well studied, meanwhile larger FNAs are at the forefront of research. Their role in the labeling and probing of biomolecules is apparent all throughout the literature, but in DNA/RNA studies, FNAs must minimally perturb the structure of the molecule and follow similar hydrogen bonding schemes to canonical base pairs in order to preserve their structure. Previous studies on the synthetic FNA 8-diethylamine-tricyclic cytosine (ABN) have peered into its unique photophysical behavior as a bright single molecule FNA and its turn on effects when base paired. As incredible a fluorophore ABN is, it is unnecessarily bulky. The ethyl groups at the 8-position can be scaled down to lessen the steric clash when inserted into oligonucleotides and still retain its push-pull characteristics. Here I present the results of TD-DFT studies (including B3LYP and aug-cc-PVDZ) into two smaller alternatives to ABN; Azetidine-ABN and 8-Dimethylamine-tricyclic cytosine. A focus is placed on maintaining qualitatively and quantitatively similar absorption and emission spectra, modeling fluorescence pathways, maintaining a HOMO-LUMO gap within range of the canonical nucleobases, and maintaining a red shifted UV-Vis spectra.

TD-DFT studies of sterically optimized fluorescent nucleoside analogues: Azetidine-ABN and dimethylamine-tricyclic cytosine

Where thousands of chemistry professionals meet to share ideas and advance scientific and technical knowledge. Spring 2023 abstracts, posters, and presentations will launch at the end of March.

ACS Spring 2023

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.