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.
Highlights
Uronic acids are reducing sugars of biological relevance
Molecules 2011, 16 has been extensively reviewed [1,2], the synthesis of uronic acid glycosides is challenging, because the presence of the C-5 carboxylic group decreases the reactivity at the anomeric position
Different methodologies have been investigated in order to overcome this drawback and to develop general strategies allowing the synthesis of uronic acid glycosides of biological importance and of complex oligosaccharides in a regio- and stereoselective manner
Summary
Uronic acids are reducing sugars of biological relevance. They are involved in the metabolism of many drugs and endogenous compounds, and they are found natural products such as glycosaminoglycans, pectins and carragenans, among others, isolated from different sources – mammals, plants and algae. Different methodologies have been investigated in order to overcome this drawback and to develop general strategies allowing the synthesis of uronic acid glycosides of biological importance and of complex oligosaccharides in a regio- and stereoselective manner. Several methods are available for the synthesis of glycosides of glucuronic acids, and these can be placed into two broad categories involving either oxidation of the corresponding glucoside or by carrying out the glycosidation on an activated glucuronic acid. L-iduronic acid has been the subject of a great number of articles dealing to the synthesis of heparin sequences, its reactions are out of the scope of this review
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