Title: Phosphoramidite building blocks for efficient incorporation of 2 '-O-aminoethoxy(and propoxy)methyl nucleosides into oligonucleotides
Authors: Bobkov, Georgii V
Mikhailov, Sergey N
Van Aerschot, Arthur
Herdewijn, Piet # ×
Issue Date: Jun-2008
Publisher: Pergamon-elsevier science ltd
Series Title: Tetrahedron vol:64 issue:27 pages:6238-6251
Abstract: A simple and efficient method for the preparation of eight phosphoramidite building blocks for incorporation of 2'-O-(2-aminoethoxymethyl)ribonucleosides and 2'-O-(3-aminopropoxymethyl)ribonucleosides into synthetic oligonucleotides has been developed. The synthetic routes are maximally convergent and provide sufficient amounts of phosphoramidites for several solid-phase synthesis coupling reactions. Using acyclic derivatives 17a,b the overall yields of phosphoramidites 2 and 3 were increased up to 50% for pyrimidine nucleosides and up to 30% for purine derivatives with substantial decrease of total reaction steps. The 2'-O-substituent was found to be stable during oligonucleotide synthesis. The resulting oligonucleotides are of particular interest for post-synthetic functionalization and conjugation. (C) 2008 Elsevier Ltd. All rights reserved.
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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