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- W2482664936 abstract "The anomeric effect in nucleosides has been little studied, probably because its contribution cannot be measured from the observable equilibrium between the preferred N and S type conformations. Theoretically, the anomeric effect is expected to be most and least favorable in the W and E type furanose conformations, respectively, which are actually barriers to interconversion between N and S. Suspecting that an O-C-N anomeric effect may nonetheless contribute to the conformational energetics of nucleosides, we have calculated the pseudorotational energy profile for various nucleoside analogs using the Tripos and Kollman force fields (Sybyl 5.5 implementation). The default parameter sets fail to reproduce the eastern barrier, the existence of which has been demonstrated by NMR studies and quantum mechanics calculations, as well as having been inferred from the distribution of crystal conformers of nucleosides. Addition of the appropriate parameters for the anomeric effect (determined by MP2/6-31G* ab initio calculations) is necessary to reproduce the known pseudorotational barrier to N-S interconversion using molecular mechanics. The addition of these or equivalent anomeric parameters to the macromolecular force fields in common use is probably essential for realistic simulations of nucleic acids, since without them interconversion between N and S furanose conformations is virtually unimpeded, leading to the disruption of unrestrained helical structures during molecular dynamics simulations." @default.
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- W2482664936 date "1993-11-23" @default.
- W2482664936 modified "2023-10-04" @default.
- W2482664936 title "O—C—N Anomeric Effect in Nucleosides" @default.
- W2482664936 doi "https://doi.org/10.1021/bk-1993-0539.ch015" @default.
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