title: Synthetic Approaches to L-Iduronic Acid and L-Idose: Key Building Blocks for the Preparation of Glycosaminoglycan Oligosaccharides.
abstract: L-Iduronic acid (IdoA) is an important monosaccharide component of glycosaminoglycans (GAGs) such as heparin, heparan sulfate and dermatan sulfate. GAGs are complex, highly sulfated polysaccharides that mediate a multitude of physiological and pathological processes via their interactions with a range of diverse proteins. The main challenge in the synthesis of GAG oligosaccharides is the efficient gram-scale preparation of IdoA building blocks since neither IdoA nor L-idose is commercially available or readily accessible from natural sources. In this review, the different synthetic approaches for the preparation of IdoA and its derivatives, including L-idose, are presented and discussed. Derivatives of the latter are often used in GAG synthesis and are elaborated to IdoA via selective oxidation at C-6 after incorporation into a GAG chain. Particular focus will be given to the preparation of IdoA synthons most commonly used for GAG oligosaccharide synthesis, and on the progress made since the last systematic review in this area.
authors.affiliation: School of Chemistry and Molecular Biosciences, The University of Queensland, Brisbane, Queensland, Australia.
authors.forename: Shifaza
authors.initials: S
authors.lastname: Mohamed
authors.affiliation: School of Chemistry and Molecular Biosciences, The University of Queensland, Brisbane, Queensland, Australia.
authors.forename: Vito
authors.initials: V
authors.lastname: Ferro
mesh_terms: D002236:Carbohydrate Conformation; D006025:Glycosaminoglycans / Q000138:chemical synthesis* / Q000737:chemistry; D006601:Hexoses / Q000138:chemical synthesis* / Q000737:chemistry; D007067:Iduronic Acid / Q000138:chemical synthesis* / Q000737:chemistry; D009844:Oligosaccharides / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D006025:Glycosaminoglycans; D006601:Hexoses; D009844:Oligosaccharides; C010997:idose; D007067:Iduronic Acid
keywords: Dermatan sulfate; Glycosaminoglycans; Glycosyl acceptors; Glycosyl donors; Heparan sulfate; Heparin; l-Idose; l-Iduronic acid