ISSN:
1434-193X
Keywords:
Trypanosoma Brucei
;
Nucleosides
;
Oligonucleotides
;
Glycosylation
;
Modified nucleobase
;
Chemistry
;
General Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
The synthesis of the recently discovered modified DNA base 5-(β-D-glucopyranosyloxymethyl)-2′-deoxyuridine (β-dJ, 1) is described. TMSOTf mediated β-glucosylation of 5-hydroxymethyl-2′-deoxyuridine (5-HMdU) derivative 10 (obtained in 20% from 2′-deoxyuridine) with trichloroacetimidate 12 gave dimer 13 in 47% yield. On the other hand, condensation of 12with N3-POM-protected derivative 20, readily available from thymidine in 48%, afforded the fully protected nucleoside 22 in 96% yield. The latter compound was converted into phosphoramidite 3 which was applied in the automated solid phase synthesis of several biological interesting β-dJ containing DNA fragments.
Additional Material:
1 Ill.
Type of Medium:
Electronic Resource
Permalink
