Oligodeoxynucleotides containing α-L-ribo configured LNA-type C-aryl nucleotides (original) (raw)

* Corresponding authors

a Nucleic Acid Center, Department of Chemistry, University of Southern Denmark, Campusvej 55, DK-5230 Odense M, Denmark
E-mail: jwe@chem.sdu.dk

b Bioorganic Laboratory, Department of Chemistry, University of Delhi, Delhi 110 007, India

c Nano-Science Center, University of Copenhagen, Universitetsparken 5, DK-2100 Copenhagen, Denmark

d Institute for Nanoscience and Engineering Technology, Department of Chemistry, University of Massachusetts, 1 University Avenue, Lowell, MA 01854, USA

Abstract

Synthesis of 2′-O,4′-_C_-methylene-α-L-ribofuranosyl derivatives containing phenyl and 1-pyrenyl aglycons, i.e., novel α-L-ribo configured LNA-type _C_-aryl nucleosides, has been accomplished. Key synthetic steps included stereoselective Grignard reactions on tetrahydrofuran aldehyde 12, configurational inversion of the resulting alcohol 13 into alcohol 15, and concomitant Mitsonobu cyclization furnishing the desired bicyclic furanosyl skeleton with a locked conformation. The phosphoramidite derivatives 19a and 19b were used for automated synthesis of 9-mer DNA and α-L-LNA oligonucleotides containing the α-L-LNA-type _C_-aryl monomers αLPhL and αLPyL containing a phenyl and pyrenyl aglycon, respectively. Thermal denaturation studies showed universal base pairing behavior for the pyrenyl monomer αLPyL when incorporated into a DNA or an α-L-LNA oligonucleotide.

Graphical abstract: Oligodeoxynucleotides containing α-l-ribo configured LNA-type C-aryl nucleotides

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Supplementary files

Copies of the 13C NMR spectra of compounds 1–4, 5–11 (of both isomers), 12, 13–18 (of phenyl and pyrenyl derivatives) and copies of the 31P NMR spectra of compounds 19a and 19b PDF (666K)

Article information

DOI

https://doi.org/10.1039/B310719A

Article type

Paper

Submitted

05 Sep 2003

Accepted

24 Oct 2003

First published

01 Dec 2003

Download Citation

Org. Biomol. Chem., 2004,2, 80-89

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