synthesis of glycosides of glucuronic, galacturonic and mannuronic acids an overview苷的合成glucuronic,galacturonic mannuronic酸概述.pdf

Molecules 2011, 16, 3933-3968; doi:10.3390/molecule OPEN ACCESS molecules ISSN 1420-3049 /journal/molecules Review Synthesis of Glycosides of Glucuronic, Galacturonic and Mannuronic Acids: An Overview Anne Wadouachi * and José Kovensky * Laboratoire des Glucides UMR CNRS 6219, Université de Picardie Jules Verne, 33 Rue Saint Leu, F-80039 Amiens, France * Authors to whom correspondence should be addressed; E-Mails: anne.wadouachi@u-picardie.fr (A.W.); jose.kovensky@u-picardie.fr (J.K.); Tel.: +33-322-827-527 (A.W.); Fax: +33-322-827- 560(A.W.); Tel.: +33-322-827-567 (J.K.); +33-322-827-568 (J.K.). Received: 24 March 2011; in revised form: 18 April 2011 / Accepted: 20 April 2011 / Published: 10 May 2011 Abstract: Uronic acids are carbohydrates present in relevant biologically active compounds. Most of the latter are glycosides or oligosaccharides linked by their anomeric carbon, so their synthesis requires glycoside-bond formation. The activation of this anomeric center remains difficult due to the presence of the electron-withdrawing C-5 carboxylic group. Herein we present an overview of glucuronidation, mannuronidation and galacturonidation reactions, including syntheses of prodrugs, oligosaccharides and stereochemical aspects. Keywords: glycosidation; glucuronic acid; galacturonic acid; mannuronic acid; stereoselectivity 1. Introduction Uronic acids are reducing sugars of biological relevance.