Synthesis of 2',3'-dideoxy-2'-fluoro-3'-thioarabinothymidine and its 3'-phosphoramidite derivative
| Autor: | Anna Lisa Tedeschi, Mohamed I. Elzagheid, Masad J. Damha |
|---|---|
| Rok vydání: | 2003 |
| Předmět: |
chemistry.chemical_classification
Phosphoramidite Oligonucleotide Stereochemistry Sodium Oligonucleotides RNA chemistry.chemical_element General Medicine Fluorine Biochemistry Amides chemistry.chemical_compound Thionucleosides chemistry Nucleic acid Genetics Molecular Medicine Nucleotide Indicators and Reagents Phosphoric Acids Arabinonucleosides Nucleoside Derivative (chemistry) Thymidine |
| Zdroj: | Nucleosides, nucleotidesnucleic acids. 22(5-8) |
| ISSN: | 1525-7770 |
| Popis: | An efficient method for the synthesis of 5′-O-monomethoxytrityl-2′,3′-dideoxy-2′-fluoro-3′-thioarabinothymidine [5′-MMTaraF-T3′SH, (5)] and its 3′-phosphoramidite derivative (6) suitable for automated incorporation into oligonucleotides, is demonstrated. A key step in the synthesis involves reaction of 5′-O-MMT-2,3′-O-anhydrothymidine (4) (Eleuteri, A.; Reese, C.B.; Song, Q., J. Chem. Soc. Perkin Trans. 1 1996, 2237 pp.) with sodium thioacetate to give 5′-MMTaraF-T3′SAc (5) (Elzagheid, M.I.; Mattila, K.; Oivanen, M.; Jones, B.C.N.M.; Cosstick, Lonnberg, H. Eur. J. Org. Chem. 2000, 1987–1991). This nucleoside was then converted to its corresponding phosphoramidite derivative, 6, as described previously ((a) Sun, S.; Yoshida, A.; Piccirilli, J.A. RNA, 1997, 3, 1352–1363; (b) Matulic-Adamic, J.; Beigelman, L. Helvetica Chemica Acta 1999, 82, 2141–2150; (c) Fettes, K.J.; O’Neil, I.; Roberts, S.M.; Cosstick, R. Nucleosides, Nucleotides and Nucl. Acids 2001, 20, 1351–1354). |
| Databáze: | OpenAIRE |
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