Synthesis of a novel bicyclic nucleoside restricted to an S-type conformation and initial evaluation of its hybridization properties when incorporated into oligodeoxynucleotides

L. Kværnø, R. H. Wightman, J. Wengel

Research output: Contribution to journalArticle

31 Citations (Scopus)

Abstract

The phosphoramidite (1S,3R,4S)-3-(2-cyanoethoxy(diisopropylamino)phosphinoxymethyl) -5-N-(4-monomethoxytrityl)-1-(uracil-1-yl)-5-aza-2-oxabicyclo[2.2.1]heptane 18 of a novel bicyclic nucleoside structure was synthesized from the known 1-(3'-deoxy-ß-D-psicofuranosyl)uracil 3. Conformational analysis of its structure verified its expected S-type furanose conformation, and the secondary amino group in the 4'-position allowed for incorporation into oligonucleotides using 5' ? 3' directed oligonucleotide synthesis as previously described for phosphoramidates. Thermal denaturation studies showed rather large decreases in duplex stabilities of -4.3 and -2.7 °C per modification toward complementary DNA and RNA, respectively.

Original languageEnglish
Pages (from-to)5106-5112
Number of pages7
JournalJournal of Organic Chemistry
Volume66
Issue number15
DOIs
Publication statusPublished - 27 Jul 2001

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