title: Conversion of yeast mannan polysaccharide in mannose oligosaccharides with a thiopropargyl linker at the pseudo-reducing end.
abstract: Polysaccharides are useful sources of preformed glycosyl linkages and therefore convenient building blocks can be prepared from them upon application of a proper degradation and derivatization scheme. Following this idea, the α-(1→6) linkages of this polysaccharide were broken applying acetolysis reaction and the pseudo-reducing position of the resulting acetylated mannose oligosaccharides was functionalized with a thiopropargyl appendage through thiourea activation of the related glycosyl iodides. Deacetylation of the final products and optimization of the purification procedures are discussed. The best yields were observed combining size exclusion chromatography and HPLC. Nine different oligosaccharides, from mono- to tetrasaccharides, mainly α-configured at the pseudo-reducing terminal, were obtained in pure form, presenting the propargyl appendage, a feature that makes them suitable substrates for successive functionalizations.
authors.affiliation: Department of Chemical Sciences, University of Napoli, Complesso Universitario Monte Sant'Angelo, Via Cintia 4, 80126 Napoli, Italy.
authors.forename: Alberto M
authors.initials: AM
authors.lastname: Marzaioli
authors.affiliation: Department of Chemical Sciences, University of Napoli, Complesso Universitario Monte Sant'Angelo, Via Cintia 4, 80126 Napoli, Italy.
authors.forename: Emiliano
authors.initials: E
authors.lastname: Bedini
authors.affiliation: Department of Chemical Sciences, University of Napoli, Complesso Universitario Monte Sant'Angelo, Via Cintia 4, 80126 Napoli, Italy.
authors.forename: Rosa
authors.initials: R
authors.lastname: Lanzetta
authors.affiliation: Department of Chemical Sciences, University of Napoli, Complesso Universitario Monte Sant'Angelo, Via Cintia 4, 80126 Napoli, Italy.
authors.forename: Michelangelo
authors.initials: M
authors.lastname: Parrilli
authors.affiliation: Department of Chemical Sciences, University of Napoli, Complesso Universitario Monte Sant'Angelo, Via Cintia 4, 80126 Napoli, Italy. Electronic address: decastro@unina.it.
authors.forename: Cristina
authors.initials: C
authors.lastname: De Castro
mesh_terms: D002845:Chromatography; D002851:Chromatography, High Pressure Liquid; D008351:Mannans / Q000737:chemistry*; D008358:Mannose / Q000737:chemistry / Q000302:isolation & purification*; D009844:Oligosaccharides / Q000737:chemistry / Q000302:isolation & purification*; D011134:Polysaccharides / Q000737:chemistry*
chemical_list: D008351:Mannans; D009844:Oligosaccharides; D011134:Polysaccharides; D008358:Mannose
keywords: Acetolysis; HPLC; NMR; Thiopropargyl; Yeast mannan