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Título: | A concise synthesis of glucuronide metabolites of urolithin-B, resveratrol, and hydroxytyrosol |
Autor: | Lucas, Ricardo CSIC; Alcántara, David CSIC; Morales, Juan C. | Palabras clave: | Resveratrol Hydroxytyrosol Urolithin-B Glucuronic metabolites Glycosylation reactions Trichloroacetimidate donor |
Fecha de publicación: | 27-jun-2009 | Editor: | Elsevier | Citación: | Carbohydrate Research 344(11): 1340-1346 (2009) | Resumen: | A simple and direct strategy to chemically synthesize O-β-d-glucuronides of urolithin-B 4, resveratrol 5, and the corresponding hydroxytyrosol derivatives 6, 7 (as a regioisomeric mixture), and 8 is described. The critical glycosylation step has been optimized using a structurally simple phenol, urolithin-B, by modification of several reaction parameters (solvent, promoter, and glucuronide donor). Very high yields have been obtained in the first synthesis of the O-β-d-glucuronide of urolithin-B 4. Extension of these reaction conditions was used for the synthesis of resveratrol-3-O-glucuronide 5 where a higher yield than previously reported was obtained by using the much more common trichloroacetimidate glucuronide donor. Finally, three O-β-d-glucuronides of hydroxytyrosol 6, 7, and 8 have been synthesized for the first time using chemical synthesis. | Descripción: | 7 páginas, 1 figura, 1 tabla, 4 esquemas | Versión del editor: | http://dx.doi.org/10.1016/j.carres.2009.05.016 | URI: | http://hdl.handle.net/10261/36190 | DOI: | 10.1016/j.carres.2009.05.016 | ISSN: | 0008-6215 |
Aparece en las colecciones: | (IIQ) Artículos |
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