Chromophoric Nucleoside Analogues: Synthesis and Characterization of 6-Aminouracil-Based Nucleodyes
Artikel i vetenskaplig tidskrift, 2016

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.


N.S. Freeman

University of California

C.E. Moore

University of California

Marcus Wilhelmsson

Kemi och kemiteknik, Kemi och biokemi, Fysikalisk kemi

Y. Tor

University of California

Journal of Organic Chemistry

0022-3263 (ISSN) 1520-6904 (eISSN)

Vol. 81 4530-4539


Nanovetenskap och nanoteknik

Livsvetenskaper och teknik


Fysikalisk kemi

Teoretisk kemi

Organisk kemi


Grundläggande vetenskaper