How does the steric effect drive the sugar conformation in the 3′-C-branched nucleosides?
- 1 January 1993
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Chemical Communications
- No. 12,p. 1011-1014
- https://doi.org/10.1039/c39930001011
Abstract
The steric effect of 3′-CH2OH group drives the North⇄ South pseudorotational equilibrium of the sugar moiety in the isomeric 1-(2′,3′-dideoxy-3′-hydroxymethyl-β-D-erythro-pentofuranosyl)cytosine 1(80% North at 298 K; ΔH°=+5.9 kJ mol–1, ΔS°=+7.4 J K–1 mol–1), and 1-(2′,3′-dideoxy-3′-hydroxymethyl-β-D-threo-pentofuranosyl)cytosine 2(82% South at 293 K; ΔH°=–0.9 kJ mol–1, ΔS°=+9.5 J K–1 mol–1) and it is found to be three times stronger in 2(ΔH°=–5.9 kJ mol–1) in comparison with that of 1(ΔH°=–2.1 kJ mo–1).Keywords
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