| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 1388284 | Carbohydrate Research | 2012 | 9 Pages |
The synthesis of β-Gal-(1→3)-α-GalNAc-(1→3)-β-GalNAc allyl trisaccharide as the outer core fragment of Burkholderia cepacia pv. vietnamiensis lipooligosaccharide was accomplished through a concise, optimized, multi-step synthesis, having as key steps three glycosylations, that were in-depth studied performing them under several conditions. The target trisaccharide was designed with an allyl aglycone in order to open a future access to the conjugation with an immunogenic protein en route to the development of a synthetic neoglycoconjugate vaccine against this Burkholderia pathogen.
Graphical abstractFigure optionsDownload full-size imageDownload as PowerPoint slideHighlights► Outer core fragment of Burkholderia cepacia pv. vietnamiensis lipooligosaccharide. ► Synthesis of trisaccharide composed of galactose and N-acetyl-galactosamine. ► Allyl aglycone on the target for future conjugation with immunogenic protein. ► Stereoselective α- or β-glycosylations with 2-azido-4,6-benzylidene-GalN donors. ► 1,2-Orthoester formation avoided in glycosylation with 2-methoxycarbonyl-Gal donor.
