A Light-Controlled Reversible DNA Photoligation via Carbazole-Tethered 5-Carboxyvinyluracil

Abstract

We describe a light-controlled template-directed reversible DNA photoligation via carbazole-tethered 5-carboxyvinyluracil. Carbazole-tethered 5-carboxyvinyl-2'-deoxyuridine-containing oligodeoxynucleotide (ODN) can be ligated by irradiation at 366 nm in the presence of template ODN, and the ligated ODN can be split by irradiation at 366 nm in the absence of template ODN.

Photoswitchable Formation of a DNA Interstrand Cross‐Link by a Coumarin‐Modified Nucleotide

“…So far neither unsubstituted nor substituted pyrimidine nucleosides have ever been applied as components of coumarin photoswitches. [35,36] This feature would be one of the important milestones for the photoswitchable DNA interstrand cross-linking. The photochromic behavior of these compounds was observed via gel electrophoresis analysis followed by UV photo-irradiation.…”

Reactions Templated by Nucleic Acids: More Ways to Translate Oligonucleotide‐Based Instructions into Emerging Function

“…[35] A further improvement in the performance of the reaction was achieved with the addition of a sensitizer covalently linked to vinyldeoxyuridine, thereby decreasing the decomposition of the oligonucleotides and making the system reversible with 366 nm light. [36] Jyo and co-workers proposed an alternative method for the templated photoligation of oligodeoxynucleotides using the photodimerization of appended anthracene tags (Figure 3.2). When templated using a perfectly matched DNA strand and with the optimal anthracene geometry, this reaction reached a high rate of conversion within minutes.…”

Templating Photoreactions in Solution

“…151,152 A particularly interesting aspect is that the photoligation can be made reversible under the irradiation conditions by using a tethered carbazole PET sensitizer. 153 Thus, irradiation in the presence of template leads to ligation, whereas irradiation in the absence of the complementary sequence leads to cleavage of photoligated strands. Such behavior may be of interest to photochemically resolve combinatorial libraries and for screening oligonucleotide strands for matching sequences.…”