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New Size‐Expanded Fluorescent Thymine Analogue: Synthesis, Characterization, and Application
Author(s) -
Hirashima Shingo,
Han Ji Hoon,
Tsuno Hitomi,
Tanigaki Yusuke,
Park Soyoung,
Sugiyama Hiroshi
Publication year - 2019
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201900843
Subject(s) - thymine , quantum yield , fluorescence , base pair , quenching (fluorescence) , nucleoside , yield (engineering) , chemistry , dna , base (topology) , combinatorial chemistry , materials science , stereochemistry , physics , biochemistry , mathematics , optics , mathematical analysis , metallurgy
Here, the synthesis, photophysical characterization, and application of a new size‐expanded thymine nucleoside, diox T , is described. diox T has desirable qualities as a T surrogate, including excellent quantum yield (0.36) and high environmental sensitivity. When incorporated into single‐ and double‐stranded DNA, diox T showed excellent photophysical characteristics including a high quantum yield (average 0.20), and unlike BgQ, demonstrated dependence on neighboring bases without significant destabilization of the duplex. Interestingly, the matched base pair of adenine (A) and diox T has the unique property that it exhibits higher fluorescence than mismatched base pairs, and diox T has self‐quenching effects. As one example of the possible applications of these promising features, single nucleoside polymorphism typing is demonstrated for discrimination of A by using diox T . The results suggest that diox T can be used for a broad range of applications in chemical biology.