title: Toward the solid-phase synthesis of heparan sulfate oligosaccharides: evaluation of iduronic acid and idose building blocks.
abstract: Glycan arrays have been established as the premier technical platform for assessing the specificity of carbohydrate binding proteins, an important step in functional glycomics research. Access to large libraries of well-characterized oligosaccharides remains a major bottleneck of glycan array research, and this is particularly true for glycosaminoglycans (GAGs), a class of linear sulfated polysaccharides which are present on most animal cells. Solid-supported synthesis is a potentially powerful tool for the accelerated synthesis of relevant GAG libraries with variations in glycan sequence and sulfation pattern. We have evaluated a series of iduronic acid and idose donors, including a couple of novel n-pentenyl orthoester donors in the sequential assembly of heparan sulfate precursors from monosaccharide building blocks in solution and on a polystyrene resin. The systematic study of donor and acceptor performance up to the trisaccharide stage in solution and on the solid support have resulted in a general strategy for the solid-phase assembly of this important class of glycans.
authors.affiliation: Biofunctional Nanomaterials Unit, CICbiomaGUNE, Paseo Miramon 182, 20009 San Sebastian, Spain.
authors.forename: Nerea
authors.initials: N
authors.lastname: Guedes
authors.forename: Pawel
authors.initials: P
authors.lastname: Czechura
authors.forename: Begoña
authors.initials: B
authors.lastname: Echeverria
authors.forename: Ada
authors.initials: A
authors.lastname: Ruiz
authors.forename: Olatz
authors.initials: O
authors.lastname: Michelena
authors.forename: Manuel
authors.initials: M
authors.lastname: Martin-Lomas
authors.forename: Niels-Christian
authors.initials: NC
authors.lastname: Reichardt
mesh_terms: D006031:Glycosylation; D006497:Heparan Sulfate / Q000138:chemical synthesis* / Q000737:chemistry; D006601:Hexoses / Q000737:chemistry*; D007067:Iduronic Acid / Q000737:chemistry*; D015394:Molecular Structure
chemical_list: D006497:Heparan Sulfate; D006601:Hexoses; D007067:Iduronic Acid; C010997:idose