Issue 16, 2001
From the journal:

Journal of the Chemical Society, Perkin Transactions 1

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

Jacob Ravn,a   Niels Thorupb  and  Poul Nielsen*a  

* Corresponding authors

a Department of Chemistry, University of Southern Denmark, Odense University, Odense, Denmark

b Department of Chemistry, Technical University of Denmark, DTU 207, Lyngby, Denmark

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 γ, 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.

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Article information

DOI
https://doi.org/10.1039/B104438A
Article type
Paper
Submitted
21 May 2001
Accepted
22 Jun 2001
First published
23 Jul 2001

J. Chem. Soc., Perkin Trans. 1, 2001, 1855-1861

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

J. Ravn, N. Thorup and P. Nielsen, J. Chem. Soc., Perkin Trans. 1, 2001, 1855 DOI: 10.1039/B104438A

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