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Synthesis of a 2'-Se-uridine phosphoramidite and its incorporation into oligonucleotides for structural study.

ABSTRACT: [chemical reaction: see text]. 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 U(Se)-A base pair and a duplex structure formation when its complementary strand was present.

SUBMITTER: Salon J

PROVIDER: S-EPMC3596769 | biostudies-other | 2005 Dec

REPOSITORIES: biostudies-other

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Synthesis of a 2'-Se-uridine phosphoramidite and its incorporation into oligonucleotides for structural study.

Salon Jozef J Chen Guexiong G Portilla Yoani Y Germann Markus W MW Huang Zhen Z

Organic letters 20051201 25

[chemical reaction: see text]. 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 ...[more]

PMID: 16321012

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