ChemInform Abstract: The Tunable Transmission of the Aromatic Character of the Aglycone Through the Anomeric Effect in C-Nucleosides Drives Its Own Sugar Conformation: A Thermodynamic Study.
✍ Scribed by I. LUYTEN; C. THIBAUDEAU; A. SANDSTROEM; J. CHATTOPADHYAYA
- Publisher
- John Wiley and Sons
- Year
- 2010
- Weight
- 32 KB
- Volume
- 28
- Category
- Article
- ISSN
- 0931-7597
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✦ Synopsis
The Tunable Transmission of the Aromatic Character of the Aglycone Through the Anomeric Effect in C-Nucleosides Drives Its Own Sugar Conformation: A Thermodynamic Study.
-The quantitation of the energetics of pD dependent North (N)(C2'-exo-C3'-endo) ↔ South (S)(C2'endo-C3'-exo) pseudorotational equilibria of the pentofuranose moiety in the C-nucleosides (I)-(IV) shows that the strength of the anomeric effect of the constituent heterocyclic moiety at C1' is dependent upon the unique aromatic nature of the nucleobases, which is tuned by the pD of the medium. The force that drives the protonation ↔ deprotonation equilibrium of the heterocyclic nucleobases in C-nucleosides is transmitted through the anomeric effect to drive the 2-state N ↔ S pseudorotational equilibrium of the constituent furanose as the energy pump.