The first synthesis of the outer core fragment of Burkholderia multivorans lipooligosaccharide [b-D-Glc- (1-3)-a-D-GalNAc-(1-3)-b-D-GalNAc-(1-3)-L-Rha] as a-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 a- and the b-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.

Synthesis of the tetrasaccharide outer core fragment of Burkholderia multivorans lipooligosaccharide / Ziaco, Marcello; DE CASTRO, Cristina; Silipo, Alba; Corsaro, MARIA MICHELA; Molinaro, Antonio; Iadonisi, Alfonso; Lanzetta, Rosa; Parrilli, Michelangelo; Bedini, Emiliano. - In: CARBOHYDRATE RESEARCH. - ISSN 0008-6215. - 403:(2015), pp. 182-191. [10.1016/j.carres.2014.04.018]

Synthesis of the tetrasaccharide outer core fragment of Burkholderia multivorans lipooligosaccharide

ZIACO, MARCELLO;DE CASTRO, CRISTINA;SILIPO, ALBA;CORSARO, MARIA MICHELA;MOLINARO, ANTONIO;IADONISI, ALFONSO;LANZETTA, ROSA;PARRILLI, MICHELANGELO;BEDINI, EMILIANO
2015

Abstract

The first synthesis of the outer core fragment of Burkholderia multivorans lipooligosaccharide [b-D-Glc- (1-3)-a-D-GalNAc-(1-3)-b-D-GalNAc-(1-3)-L-Rha] as a-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 a- and the b-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.
2015
Synthesis of the tetrasaccharide outer core fragment of Burkholderia multivorans lipooligosaccharide / Ziaco, Marcello; DE CASTRO, Cristina; Silipo, Alba; Corsaro, MARIA MICHELA; Molinaro, Antonio; Iadonisi, Alfonso; Lanzetta, Rosa; Parrilli, Michelangelo; Bedini, Emiliano. - In: CARBOHYDRATE RESEARCH. - ISSN 0008-6215. - 403:(2015), pp. 182-191. [10.1016/j.carres.2014.04.018]
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11588/579223
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