Title: Phospho-carboxylic anhydride of a homologated nucleoside leads to primer degradation in the presence of a polymerase
Authors: Kachare, Dhuldeo
Song, Xiao-Ping
Herdewijn, Piet # ×
Issue Date: Jun-2014
Publisher: Pergamon Press
Series Title: Bioorganic & Medicinal Chemistry Letters vol:24 issue:12 pages:2720-3
Article number: 10.1016/j.bmcl.2014.04.042
Abstract: Starting from thymidine, through a series of key synthetic transformations (e.g., Wittig reaction, hydroboration, Mitsunobu reaction and TEMPO oxidation) a nucleoside homologue bearing a phospho-carboxylic anhydride group at 6' position was synthesized. The potential of polymerases to catalyze amide bond formation was investigated by using a modified primer with an amino group at 3' position and the synthesized phosphoanhydro compound as substrate. Unfortunately, we did not observe the desired product either by gel electrophoresis or mass spectrometry. In contrast, the instability of the phosphoanhydro compound could lead to pyrophosphate formation and thus, to pyrophosphorolysis of the primer rather than to primer extension.
ISSN: 0960-894X
Publication status: published
KU Leuven publication type: IT
Appears in Collections:Medicinal Chemistry (Rega Institute)
× corresponding author
# (joint) last author

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