title: Conformational changes of 1-4-glucopyranosyl residues of a sulfated C-C linked hexasaccharide.
abstract: This work describes the structure of a fully sulfated maltotriose alpha-beta C-C linked dimer, where a central glycosidic bond was substituted by a non natural, hydrolase-resistant C-C bond. Such compound shows anti-metastatic properties being an inhibitor of the heparanase enzymatic activity and of P-selectin-mediated cell-cell interactions. NMR spectroscopy was applied to investigate the structure and conformational properties of this C-C linked hexasaccharide. The presence of sulfate substituents and the internal C-C bond drives the two internal rings in an unusual (1)C(4) chair conformation, while the external rings linked by glycosidic bonds retain the typical (4)C(1) conformation. The NMR results were confirmed by molecular mechanics calculations using structure corresponding di- and tetrasaccharides as models.
authors.affiliation: Department of Chemistry, Materials and Chemical Engineering 'G. Natta', Politecnico di Milano, via L. Mancinelli 7, 20131 Milano, Italy.
authors.forename: Alessia
authors.initials: A
authors.lastname: Coletti
authors.affiliation: 'G. Ronzoni' Institute for Chemical and Biochemical Research, via G. Colombo 81, 20133 Milano, Italy. Electronic address: elli@ronzoni.it.
authors.forename: Stefano
authors.initials: S
authors.lastname: Elli
authors.affiliation: 'G. Ronzoni' Institute for Chemical and Biochemical Research, via G. Colombo 81, 20133 Milano, Italy.
authors.forename: Eleonora
authors.initials: E
authors.lastname: Macchi
authors.affiliation: Department of Chemistry, Materials and Chemical Engineering 'G. Natta', Politecnico di Milano, via L. Mancinelli 7, 20131 Milano, Italy.
authors.forename: Patrizia
authors.initials: P
authors.lastname: Galzerano
authors.affiliation: Department of Chemistry, Yazd University, PO Box 89195-741, Yazd, Iran.
authors.forename: Leila
authors.initials: L
authors.lastname: Zamani
authors.affiliation: 'G. Ronzoni' Institute for Chemical and Biochemical Research, via G. Colombo 81, 20133 Milano, Italy.
authors.forename: Marco
authors.initials: M
authors.lastname: Guerrini
authors.affiliation: 'G. Ronzoni' Institute for Chemical and Biochemical Research, via G. Colombo 81, 20133 Milano, Italy.
authors.forename: Giangiacomo
authors.initials: G
authors.lastname: Torri
authors.affiliation: Department of Chemistry, Materials and Chemical Engineering 'G. Natta', Politecnico di Milano, via L. Mancinelli 7, 20131 Milano, Italy.
authors.forename: Elena
authors.initials: E
authors.lastname: Vismara
mesh_terms: D002236:Carbohydrate Conformation; D019281:Dimerization; D005947:Glucose / Q000737:chemistry*; D008958:Models, Molecular; D009844:Oligosaccharides / Q000737:chemistry*; D013431:Sulfates / Q000737:chemistry*
chemical_list: D009844:Oligosaccharides; D013431:Sulfates; D005947:Glucose
keywords: (1)C(4) chair conformation; Maltotriose; Molecular mechanics; NOESY spectroscopy; Sulfated CC oligosaccharides; Sulfated oligosaccharide-based drugs