Journal
NATURE CHEMISTRY
Volume 8, Issue 2, Pages 186-191Publisher
NATURE PUBLISHING GROUP
DOI: 10.1038/NCHEM.2399
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Funding
- Agence Nationale de la Recherche (ANR) [ANR-12-BS07-0003-01]
- Foundation for the Development of the Chemistry of Natural Products of the French Academy of Sciences
- French Centre National de la Recherche Scientifique, (PICS program)
- ANR [ANR-12-BS07-0003-01]
- Regional Council Poitou-Charentes
- University of Poitiers
- Ministery of Economy and Competitiveness of Spain [CTQ2012-32025]
- Agence Nationale de la Recherche (ANR) [ANR-12-BS07-0003] Funding Source: Agence Nationale de la Recherche (ANR)
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Glycosyl cations are universally accepted key ionic intermediates in the mechanism of glycosylation, the reaction that covalently links carbohydrates to other molecules. These ions have remained hypothetical species so far because of their extremely short life in organic media as a consequence of their very high reactivity. Here, we report the use of liquid hydrofluoric acid-antimony pentafluoride (HF/SbF5) superacid to generate and stabilize the glycosyl cations derived from peracetylated 2-deoxy and 2-bromoglucopyranose in a condensed phase. Their persistence in this superacid medium allows their three-dimensional structure to be studied by NMR, aided by complementary computations. Their deuteration further confirms the impact of the structure of the glycosyl cation on the stereochemical outcome of its trapping.
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