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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| Authors: | Henrik M Pfundheller Alexei A Koshkin Carl Erik Olsen Jesper Wengel |
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| Institution: | 1. Department of Chemistry , University of Southern Denmark, Odense University , DK-5230, Odense M, Denmark;2. Center for Synthetic Bioorganic Chemistry, Department of Chemistry, Chemical Laboratory II , University of Copenhagen , Universitetsparken 5, DK-2100, Copenhagen, Denmark;3. Exiqon A/S , Bygstubben 9, DK-2950, Vedbék, Denmark;4. Department of Chemistry , The Royal Veterinary and Agricultural University , DK-1871, Frederiksberg C, Denmark;5. Center for Synthetic Bioorganic Chemistry, Department of Chemistry, Chemical Laboratory II , University of Copenhagen , Universitetsparken 5, DK-2100, Copenhagen, Denmark |
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| Abstract: | 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-dioxabicyclo3.3.0]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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