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Synthesis of Oligodeoxynucleotides Containing 5-(β-D-Glucopyranosyloxymethyl)-2′-deoxyuridine, a Modified Nucleoside in the DNA of Trypanosoma Brucei by Martin de Kort; Edwin Ebrahimi; Eric R. Wijsman; Gijs A. van der Marel; Jacques H. van Boom is a Chemistry article available to read on EtoBox.

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The synthesis of the recently discovered modified DNA base derivative 20, readily available from thymidine in 48%, afforded the fully protected nucleoside 22 in 96% yield. The 5-(β-D-glucopyranosyloxymethyl)-2Ј-deoxyuridine (β-dJ, 1) is described. TMSOTf mediated β-glucosylation of latter compound was converted into phosphoramidite 3 which was applied in the automated solid phase synthesis of 5-hydroxymethyl-2Ј-deoxyuridine (5-HMdU) derivative 10 (obtained in 20% from 2Ј-deoxyuridine) with several biological interesting β-dJ containing DNA fragments. trichloroacetimidate 12 gave dimer 13 in 47% yield. On the other hand, condensation of 12 with N 3 -POM-protected

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Author

Martin de Kort; Edwin Ebrahimi; Eric R. Wijsman; Gijs A. van der Marel; Jacques H. van Boom

Publisher

John Wiley and Sons; Wiley (John Wiley & Sons); John Wiley & Sons Ltd.; Wiley (ISSN 1434-193X)

Published

1999

Language

EN

Field

Chemistry (Physical Sciences)