Abstract
Fucosylated chondroitin sulfate (fCS) is a glycosaminoglycan (GAG) polysaccharide with a unique structure, displaying a backbone composed of alternating N-acetyl-d-galactosamine (GalNAc) and d-glucuronic acid (GlcA) units on which l-fucose (Fuc) branches are installed. fCS shows several potential biomedical applications, with the anticoagulant activity standing as the most promising and widely investigated one. Natural fCS polysaccharides extracted from marine organisms (Echinoidea, Holothuroidea) present some advantages over a largely employed antithrombotic drug such as heparin, but some adverse effects as well as a frequently found structural heterogeneity hamper its development as a new drug. To circumvent these drawbacks, several efforts have been made in the last decade to obtain synthetic and semi-synthetic fCS oligosaccharides and low molecular weight polysaccharides. In this Review we have for the first time collected these reports together, dividing them in two topics: (i) total syntheses of fCS oligosaccharides and (ii) semi-synthetic approaches to fCS oligosaccharides and low molecular weight polysaccharides as well as glycoclusters displaying multiple copies of fCS species.
Highlights
Glycosaminoglycans (GAGs) are highly negatively charged polysaccharides ubiquitously distributed in the animal kingdom
Fuc monosaccharide building blocks. analysis of a library of diNifantiev and GalNAc co-workers reported the synthesis and conformational and trisaccharide fragments carrying Fuc branches differing by length, sulfation pattern and site of Nifantiev and co-workers reported the synthesis and conformational analysis of a library of diand trisaccharide fragments carrying Fuc branches differing by length, sulfation pattern and site of linkage [32,33,34]
Trisaccharide to the core moiety, gave an intrinsic pathway inhibition activity comparable or even higher than hexa, octa- and nonavalent glycoclusters 59–62 designed with a longer linker between the oligosaccharides and the core region [41]. These findings clearly indicated that the arrangement of the Fucosylated chondroitin sulfate (fCS) repeating units in the glycoclusters makes great difference on the bioactivity
Summary
Glycosaminoglycans (GAGs) are highly negatively charged polysaccharides ubiquitously distributed in the animal kingdom. Analysis of a library of diNifantiev and GalNAc co-workers reported the synthesis and conformational and trisaccharide fragments carrying Fuc branches differing by length, sulfation pattern and site of Nifantiev and co-workers reported the synthesis and conformational analysis of a library of diand trisaccharide fragments carrying Fuc branches differing by length, sulfation pattern and site of linkage [32,33,34] These serve as simple model compounds covering the structural variability of native fCS, including the less frequent cases of Fuc units linked at GalNAc O-6 instead of GlcA O-3 linkage [32,33,34]. 24 byby chloroacetylation, de-O-allylation andand installation of aoftrichloroacetimidate leaving group at the the anomeric position furnished disaccharide donor that was in turn glycosylated with anomeric position furnished disaccharide donor that was in turn glycosylated with GlcA acceptor acceptor
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