原创力文档synthesis of glycosides of glucuronic, galacturonic and mannuronic acids an overview苷的合成glucuronic,galacturonic mannuronic酸概述.pdfVIP
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synthesis of glycosides of glucuronic, galacturonic and mannuronic acids an overview苷的合成glucuronic,galacturonic mannuronic酸概述
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.
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