Title: Synthesis of 3'-deoxy-3'-c-hydroxymethyl-aldopentopyranosyl nucleosides and their incorporation in oligonucleotides .2
Authors: Doboszewski, Bogdan ×
De Winter, H
Van Aerschot, Arthur
Herdewijn, Piet #
Issue Date: Nov-1995
Publisher: Pergamon-elsevier science ltd
Series Title: Tetrahedron vol:51 issue:45 pages:12319-12336
Abstract: The synthesis of 3'-deoxy-3'-C-hydroxymethyl-aldopentopyranosyl nucleosides using an intramolecular radical C-C bond formation reaction is described. This method gives good results for the synthesis of thymine and adenine nucleosides, but not for cytosine and guanine nucleosides. Dependent on the configuration (beta-D-erythro or alpha-L-threo), the conformation of the adenine nucleosides is clearly different (axial base moiety for alpha-D-erythro and equatorial adenine base for alpha-L-threo nucleosides) which could be explained by the gauche effect. Oligonucleotides built up of 2',3'-dideoxy-3'-C-hydroxymethyl-alpha-L-threo-pentopyranosyl adenine are able to form duplexes with oligothymidylate although with less stability than natural dsDNA.
ISSN: 0040-4020
Publication status: published
KU Leuven publication type: IT
Appears in Collections:Medicinal Chemistry (Rega Institute)
× corresponding author
# (joint) last author

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