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As part of an ongoing project aimed at identifying protective capsular polysaccharide epitopes for the development of vaccine candidates against the fungal pathogen Cryptococcus neoformans, the synthesis and glycosylation properties of a naphthalenylmethyl (NAP) orthogonally protected trisaccharide thioglycoside, a common building block for construction of serotype B and C capsular polysaccharide structures, were investigated. Et (benzyl 2,3,4-tri-O-benzyl-β-D-glucopyranosyl-uronate)-(1→2)-[2,3,4-tri-O-benzyl-β-D-xylopyranosyl-(1→4)]-6-O-benzyl-3-O-(2-naphthalenylmethyl)-1-thio-α-D-mannopyranoside was prepd. and used both as a donor and an acceptor in glycosylation reactions to obtain spacer equipped hexa- and heptasaccharide structures suitable either for continued elongation or for deprotection and printing onto a glycan array or conjugation to a carrier protein. The glycosylation reactions proceeded with high yields and α-selectivity, proving the viability of the building block approach also for construction of 4-O-xylosyl-contg. C. neoformans CPS structures

Mandatory Citation Fields
Publication Subcategory	Research Papers
Authors	Guazzelli, Lorenzo; Ulc, Rebecca; Oscarson, Stefan
Year	2015	Month	August
Article Title	Synthesis of a Glucuronic Acid-Containing Thioglycoside Trisaccharide Building Block and Its Use in the Assembly of Cryptococcus Neoformans Capsular Polysaccharide Fragments
Researcher's Role	Author
Status	In Press	Peer Reviewed

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Search Keyword	Please enter separate search keywords on separate lines Synthesis of a Glucuronic Acid-Containing Thioglycoside Trisaccharide Building Block and Its Use in the Assembly of Cryptococcus Neoformans Capsular Polysaccharide Fragments
Short Description	Synthesis of a Glucuronic Acid-Containing Thioglycoside Trisaccharide Building Block and Its Use in the Assembly of Cryptococcus Neoformans Capsular Polysaccharide Fragments
Abstract	As part of an ongoing project aimed at identifying protective capsular polysaccharide epitopes for the development of vaccine candidates against the fungal pathogen Cryptococcus neoformans, the synthesis and glycosylation properties of a naphthalenylmethyl (NAP) orthogonally protected trisaccharide thioglycoside, a common building block for construction of serotype B and C capsular polysaccharide structures, were investigated. Et (benzyl 2,3,4-tri-O-benzyl-β-D-glucopyranosyl-uronate)-(1→2)-[2,3,4-tri-O-benzyl-β-D-xylopyranosyl-(1→4)]-6-O-benzyl-3-O-(2-naphthalenylmethyl)-1-thio-α-D-mannopyranoside was prepd. and used both as a donor and an acceptor in glycosylation reactions to obtain spacer equipped hexa- and heptasaccharide structures suitable either for continued elongation or for deprotection and printing onto a glycan array or conjugation to a carrier protein. The glycosylation reactions proceeded with high yields and α-selectivity, proving the viability of the building block approach also for construction of 4-O-xylosyl-contg. C. neoformans CPS structures
Publisher Location	ChemistryOpen
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DOI Link	10.1002/open.201500143
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