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Synthesis of a 2‘-Se-uridine Phosphoramidite and Its Incorporation into Oligonucleotides for Structural Study

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journal contribution
posted on 08.12.2005, 00:00 by Jozef Salon, Guexiong Chen, Yoani Portilla, Markus W. Germann, Zhen Huang
We report here the synthesis of the 5‘-[benzhydryloxybis(trimethylsilyloxy)]silyl-2‘-methylseleno-2‘-deoxyuridine phosphoramidite and its incorporation into oligonucleotides by solid-phase synthesis. The coupling yield of this phosphoramidite into oligonucleotides is higher than 99%. We also demonstrate that this 2‘-methylselenophosphoramidite is compatible with the 5‘-silyl-2‘-ACE chemistry, for longer Se-RNA solid-phase synthesis. Our preliminary NMR study on the synthesized 2‘-Se-DNA has revealed a USe−A base pair and a duplex structure formation when its complementary strand was present.