Evaluation of Oligonucleotides Containing Two Novel 2′-O-Methyl Modified Nucleotide Monomers: A 3′-C-Allyl and a 2′-O-3′-C-Linked Bicyclic Derivative

Henrik M. Pfundheller Department of Chemistry, University of Southern Denmark, Odense University, DK-5230, Odense M, Denmark

Alexei A. Koshkin Center for Synthetic Bioorganic Chemistry, Department of Chemistry, Chemical Laboratory II, University of Copenhagen, Universitetsparken 5, DK-2100, Copenhagen, Denmark; Exiqon A/S, Bygstubben 9, DK-2950, Vedbék, Denmark

Carl Erik Olsen Department of Chemistry, The Royal Veterinary and Agricultural University, DK-1871, Frederiksberg C, Denmark

Jesper Wengel Center for Synthetic Bioorganic Chemistry, Department of Chemistry, Chemical Laboratory II, University of Copenhagen, Universitetsparken 5, DK-2100, Copenhagen, Denmark

Abstract

The two ribo-configured nucleosides 1-(3-C-allyl-2–0-methyl-β-D-ribo-pentofuranosyl)thymine 3 and (1S,5R,6R,8R)-5-hydroxy-6-(hydroxymethyl)-1-methoxy-8-(thymin-1-yl)-2,7-dioxabicyclo[3.3.0]octane 6 have been transformed into their corresponding phosphoramidites, 5 and 8 respectively, and used as building blocks for the synthesis of modified oligonucleotides. The oligonucleotides were shown to hybridize with decreased binding affinity towards complementary single stranded DNA and RNA.

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Evaluation of Oligonucleotides Containing Two Novel 2′-O-Methyl Modified Nucleotide Monomers: A 3′-C-Allyl and a 2′-O-3′-C-Linked Bicyclic Derivative

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Evaluation of Oligonucleotides Containing Two Novel 2′-O-Methyl Modified Nucleotide Monomers: A 3′-C-Allyl and a 2′-O-3′-C-Linked Bicyclic Derivative

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