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Synthesis of Oligodeoxynucleotides Containing 5-(β-D-Glucopyranosyloxymethyl)-2′-deoxyuridine, a Modified Nucleoside in the DNA of Trypanosoma Brucei

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

Publisher
John Wiley and Sons
Year
1999
Tongue
English
Weight
257 KB
Volume
1999
Category
Article
ISSN
1434-193X

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✦ Synopsis

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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