A conformationally locked tricyclic nucleoside. Synthesis, crystal structure and incorporation into oligonucleotides

Jacob Ravn, Niels Thorup, Poul Nielsen

Research output: Contribution to journalJournal articleResearchpeer-review

Abstract

A tricyclic nucleoside is synthesised from a bicyclic nucleoside precursor by applying a stereoselective dihydroxylation, a regioselective tosylation and an intramolecular ether formation. This tricyclic nucleoside is constructed as a conformationally locked thymidine analogue and has been analysed by X-ray crystallography. Thus, the furanose ring of this nucleoside adopts a perfect S-type conformation and the torsion angle gamma, describing the C4'-C5' bond is restricted in the +ac range. The tricyclic nucleoside is incorporated into two nonameric oligonucleotide sequences displaying strongly decreased affinity towards complementary DNA and RNA when compared to the corresponding unmodified oligodeoxynucleotide sequences.
Original languageEnglish
JournalRoyal Chemical Society. Journal. Perkin Transactions 1
Volume1
Issue number16
Pages (from-to)1855-1861
ISSN1472-7781
DOIs
Publication statusPublished - 2001

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