Isotopic labelling of quercetin 3-glucoside |
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Authors: | Stuart T Caldwell Louis J Farrugia Alan Crozier |
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Institution: | a WestCHEM Department of Chemistry, University of Glasgow, Glasgow G12 8QQ, UK b Division of Biochemistry and Molecular Biology, University of Glasgow, Glasgow G12 8QQ, UK |
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Abstract: | The potentially important dietary antioxidant, quercetin 3-O-β-d-glucoside, has been 13C-labelled at C-2 of the flavonoid unit by synthesis in 15% yield over five steps from 13C]carbon dioxide. The route is appropriate for radiochemical synthesis. Formation of the protected 3-glucosylated flavonol appears to result from 1,7]-sigmatropic rearrangement with migration of a benzyl group followed by cyclisation. A free 5-OH results even when a phosphazene superbase is used. |
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