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.
Publication types
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Research Support, N.I.H., Extramural
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Research Support, Non-U.S. Gov't
MeSH terms
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Deoxyuridine / analogs & derivatives*
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Deoxyuridine / chemical synthesis
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Deoxyuridine / chemistry
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Molecular Structure
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Nuclear Magnetic Resonance, Biomolecular
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Oligonucleotides / chemistry*
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Organophosphorus Compounds / chemical synthesis*
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Organoselenium Compounds / chemical synthesis*
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Organoselenium Compounds / chemistry
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Uridine / analogs & derivatives*
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Uridine / chemical synthesis
Substances
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5'-(benzhydryloxybis(trimethylsilyloxy))silyl-2'-methylseleno-2'-deoxyuridine phosphoramidite
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Oligonucleotides
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Organophosphorus Compounds
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Organoselenium Compounds
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uridine phosphoramidite
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Deoxyuridine
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Uridine