Title: Synthesis and conformational analysis of a ribo-type cyclohexenyl nucleoside
Authors: Vijgen, Sara ×
Nauwelaerts, Koen
Wang, Jing
Van Aerschot, Arthur
Lagoja, Irene
Herdewijn, Piet #
Issue Date: Jun-2005
Series Title: Journal of Organic Chemistry vol:70 issue:12 pages:4591-4597
Abstract: A straightforward approach to a novel class of ribo-type cyclohexenyl nucleosides is described. An electron-demand Diels-Alder reaction forms the key-step of the chosen synthetic pathway. Although the difference is small, conformational analysis using NMR shows that this nucleoside analogue adopts preferentially an 2H3 conformation (S-type), while the "deoxy" cyclohexenyl analogue has a preference for a C3' endo conformation (N-type). Analyses of the conformational equilibrium reveal that, in the given experimental conditions, the difference between adenosine and its cyclohexenyl congener resides in their different DeltaG values; furthermore, in adenosine, the conformational preference is of enthalpic origin, whereas in the cyclohexenyl congener, the conformational preference is of entropic origin.
ISSN: 0022-3263
Publication status: published
KU Leuven publication type: IT
Appears in Collections:Medicinal Chemistry (Rega Institute)
× corresponding author
# (joint) last author

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