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- W2003156586 abstract "The effect of ring-oxygen protonation on the structure and conformational properties of a model deoxyaldofuranose, 2-deoxy-β-d-glycero-tetrofuranose 2, has been examined with the use of NMR spectroscopy and ab initio molecular orbital calculations conducted at the HF/6-31G* level of theory. The computational method was validated by comparing the conformational behavior of 2 derived from PSEUROT treatment of 3JHH values measured in 2 (2H2O solvent) with that predicted from the theoretical calculations. Coupling data indicate that 2 favors S forms in solution (∼89% 4T3, ∼11% E2), while MO data indicated more comparable populations of the same or very similar N and S forms. Protonation of 2 at the ring oxygen (O4), yielding 1, gave two distinct protonated forms which differed in the orientation of the proton about O4. Both forms showed substantial changes in ring structure and conformation compared to 2. Protonated forms almost exclusively prefer S forms (E3), and energy barriers for N/S interconversion were..." @default.
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- W2003156586 date "1997-09-01" @default.
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- W2003156586 title "Carbohydrate Reaction Intermediates: Effect of Ring-Oxygen Protonation on the Structure and Conformation of Aldofuranosyl Rings" @default.
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- W2003156586 doi "https://doi.org/10.1021/ja963727p" @default.
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