title: Synthesis of the tetrasaccharide outer core fragment of Burkholderia multivorans lipooligosaccharide.
abstract: The first synthesis of the outer core fragment of Burkholderia multivorans lipooligosaccharide [β-D-Glc-(1→3)-α-D-GalNAc-(1→3)-β-D-GalNAc-(1→3)-L-Rha] as α-allyl tetrasaccharide was accomplished. The glycosylations involving GalNAc units were studied in depth testing them under several conditions. This allowed the building of both the α- and the β-configured glycosidic bonds by employing the same GalNAc glycosyl donor, thus considerably shortening the total number of synthetic steps. The target tetrasaccharide was synthesized with an allyl aglycone to allow its future conjugation with an immunogenic protein en route to the development of a synthetic neoglycoconjugate vaccine against the Burkholderia cepacia pathogens.
authors.affiliation: Department of Chemical Sciences, University of Naples Federico II, Complesso Universitario Monte S.Angelo, Via Cintia 4, 80126 Napoli, Italy.
authors.forename: Marcello
authors.initials: M
authors.lastname: Ziaco
authors.affiliation: Department of Chemical Sciences, University of Naples Federico II, Complesso Universitario Monte S.Angelo, Via Cintia 4, 80126 Napoli, Italy.
authors.forename: Cristina
authors.initials: C
authors.lastname: De Castro
authors.affiliation: Department of Chemical Sciences, University of Naples Federico II, Complesso Universitario Monte S.Angelo, Via Cintia 4, 80126 Napoli, Italy.
authors.forename: Alba
authors.initials: A
authors.lastname: Silipo
authors.affiliation: Department of Chemical Sciences, University of Naples Federico II, Complesso Universitario Monte S.Angelo, Via Cintia 4, 80126 Napoli, Italy.
authors.forename: Maria Michela
authors.initials: MM
authors.lastname: Corsaro
authors.affiliation: Department of Chemical Sciences, University of Naples Federico II, Complesso Universitario Monte S.Angelo, Via Cintia 4, 80126 Napoli, Italy.
authors.forename: Antonio
authors.initials: A
authors.lastname: Molinaro
authors.affiliation: Department of Chemical Sciences, University of Naples Federico II, Complesso Universitario Monte S.Angelo, Via Cintia 4, 80126 Napoli, Italy.
authors.forename: Alfonso
authors.initials: A
authors.lastname: Iadonisi
authors.affiliation: Department of Chemical Sciences, University of Naples Federico II, Complesso Universitario Monte S.Angelo, Via Cintia 4, 80126 Napoli, Italy.
authors.forename: Rosa
authors.initials: R
authors.lastname: Lanzetta
authors.affiliation: Department of Chemical Sciences, University of Naples Federico II, Complesso Universitario Monte S.Angelo, Via Cintia 4, 80126 Napoli, Italy.
authors.forename: Michelangelo
authors.initials: M
authors.lastname: Parrilli
authors.affiliation: Department of Chemical Sciences, University of Naples Federico II, Complesso Universitario Monte S.Angelo, Via Cintia 4, 80126 Napoli, Italy. Electronic address: ebedini@unina.it.
authors.forename: Emiliano
authors.initials: E
authors.lastname: Bedini
mesh_terms: D016956:Burkholderia cepacia / Q000737:chemistry*; D002240:Carbohydrate Sequence; D060326:Chemistry Techniques, Synthetic; D006027:Glycosides / Q000737:chemistry; D006031:Glycosylation; D008070:Lipopolysaccharides / Q000737:chemistry*; D008969:Molecular Sequence Data; D009844:Oligosaccharides / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D006027:Glycosides; D008070:Lipopolysaccharides; D009844:Oligosaccharides; C023023:lipid-linked oligosaccharides
keywords: Burkholderia cepacia; Glucose; Glycosylation; N-Acetyl-galactosamine; Oligosaccharide; Rhamnose