An efficient method for the synthesis of selenium modified nucleosides: its application in the synthesis of Se-adenosyl-L-selenomethionine (SeAM)
In this paper, we report that a versatile method for the synthesis of 5'-selenium modified nucleosides has been explored on the basis of a 2-(trimethylsilyl)ethyl (TSE) selenyl group as a selenating donor. We demonstrate the broad utility of this method through direct introduction of various fu...
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| Veröffentlicht in: | Organic & biomolecular chemistry 2015-01, Vol.13 (36), p.9405-9417 |
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| container_title | Organic & biomolecular chemistry |
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| creator | Kogami, Masakazu Koketsu, Mamoru |
| description | In this paper, we report that a versatile method for the synthesis of 5'-selenium modified nucleosides has been explored on the basis of a 2-(trimethylsilyl)ethyl (TSE) selenyl group as a selenating donor. We demonstrate the broad utility of this method through direct introduction of various functional groups into 5'-TSE-selenonucleosides. This original method offers additional advantages for the preparation of these compounds, such as high functional group tolerance, ready availability of various electrophilic reagents, mild conditions, simple operation, and good yields. The utility of this approach is further demonstrated by the synthesis of Se-adenosyl-L-selenomethionine (SeAM) as a chemical reporter for methyltransferases. |
| doi_str_mv | 10.1039/c5ob01316j |
| format | Article |
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| ispartof | Organic & biomolecular chemistry, 2015-01, Vol.13 (36), p.9405-9417 |
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| source | MEDLINE; Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection |
| subjects | Methyltransferases - metabolism Molecular Structure Nucleosides - chemical synthesis Nucleosides - chemistry Selenium - chemistry Selenomethionine - chemical synthesis Selenomethionine - chemistry Selenomethionine - metabolism |
| title | An efficient method for the synthesis of selenium modified nucleosides: its application in the synthesis of Se-adenosyl-L-selenomethionine (SeAM) |
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