5-Bromouridine oligonucleotides were synthesized directly from 5-bromouridine by a polycondensation method. The reaction of 5-bromouridine with tri(imidazol-1-yl)phosphine was carried out at a relatively low temperature and the subsequent in situ oxidation of the resulting phosphite oligomer was achieved with iodine and water. 5-Bromouridine oligonucleotides up to a hexamer were obtained in high yields. The phosphodiester linkage of the oligomer consists of both 3′,5′- and 2′,5′-linkages. The interaction of 5-bromouridine oligonucleotides with poly A was investigated.
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After 5 min oxidation, unreacted iodine was quenched with NaHSO3. The 31P NMR signal due to phosphite 4 was observed at this stage.10 The oxidation of phosphite 4 to phosphate 5 was completed within 30 min.
Judging from the melting curve in Figure 4, two kinds of the hydrogen-bonded complexes were existed; at 20°C 2-oligo 5-BrU-poly A complex was melted to oligo 5-BrU+oligo 5-BrU-poly A and at 27°C oligo 5-BrU-poly A complex was transformed into oligo 5-BrU+poly A. Tm value of the complex between oligo 5-BrU and poly A was roughly estimated to be 25°C. The Tm value of the complex between poly U and 3′,5′-oligo A was observed slightly higher than that of the complex between poly U and 2′,5′-oligo A.13 Therefore, the Tm value obtained here is probably not so different from that of the poly A–3′,5′-oligo 5-BrU complex.
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Shimidzu, T., Yamana, K. Synthesis of 5-Bromouridine Oligonucleotides by the Reaction of 5-Bromouridine with Tri(imidazol-1-yl)phosphine. Polym J 15, 727–732 (1983). https://doi.org/10.1295/polymj.15.727
- 5-Bromouridine Oligonucleotide
- Phosphodiester Linkage
- Interaction of 5-Bromouridine Oliogonucleotide
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