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Chromophoric Nucleoside Analogues: Synthesis and Characterization of 6-Aminouracil-Based Nucleodyes

N.S. Freeman ; C.E. Moore ; Marcus Wilhelmsson (Institutionen för kemi och kemiteknik, Fysikalisk kemi) ; Y. Tor
Journal of Organic Chemistry (0022-3263). Vol. 81 (2016), 11, p. 4530-4539.
[Artikel, refereegranskad vetenskaplig]

Nucleodyes, visibly colored chromophoric nucleoside analogues, are reported. Design criteria are outlined and the syntheses of cytidine and uridine azo dye analogues derived from 6-aminouracil are described. Structural analysis shows that the nucleodyes are sound structural analogues of their native nucleoside counterparts, and photophysical studies demonstrate that the nucleodyes are sensitive to microenvironmental changes. Quantum chemical calculations are presented as a valuable complementary tool for the design of strongly absorbing nucleodyes, which overlap with the emission of known fluorophores. Förster critical distance (R0) calculations determine that the nucleodyes make good FRET pairs with both 2-aminopurine (2AP) and pyrrolocytosine (PyC). Additionally, unique tautomerization features exhibited by 5-(4-nitrophenylazo)-6-oxocytidine (8) are visualized by an extraordinary crystal structure.

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Denna post skapades 2016-07-01. Senast ändrad 2016-09-09.
CPL Pubid: 238795


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