Taxonomic group: fungi / Basidiomycota
(Phylum: Basidiomycota)
Organ / tissue: capsuleAssociated disease: infection due to Cryptococcus neoformans [ICD11:
XN3EH 
];
infection due to Cryptococcus gattii [ICD11:
XN0LE ]
NCBI PubMed ID: 27308199Publication DOI: 10.1002/open.201500143Journal NLM ID: 101594811Publisher: Weinheim: Wiley-VCH
Correspondence: stefan.oscarson
ucd.ie
Institutions: School of Chemistry and Chemical Biology, University College Dublin, Dublin, Ireland
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. Ethyl (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 prepared 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-containing C. neoformans CPS structures.
carbohydrates, capsular polysaccharide, block synthesis, Thioglycosides, Cryptococcus neoformans
Structure type: suggested polymer biological repeating unit
Location inside paper: Fig. 1, B
Trivial name: glucuronoxylomannan (GXM), glucuronoxylomannan
Compound class: CPS, EPS, O-polysaccharide, O-antigen, cell wall polysaccharide, polysaccharide, glucuronoxylomannan, capsule polysaccharide
Contained glycoepitopes: IEDB_114701,IEDB_115136,IEDB_115576,IEDB_130701,IEDB_140116,IEDB_140630,IEDB_144983,IEDB_145668,IEDB_152206,IEDB_164174,IEDB_167188,IEDB_174332,IEDB_2270799,IEDB_423153,IEDB_76933,IEDB_983930,SB_197,SB_44,SB_67,SB_72
Methods: chemical synthesis
Synthetic data: chemical
Comments, role: chemical repeating unit frame was shifted in annotation for compatibility with structures elucidated by MS [Eukaryotic Cell 2007, 6: 1464-1473]
Related record ID(s): 48292, 48294, 48295
NCBI Taxonomy refs (TaxIDs): 37769Reference(s) to other database(s): GTC:G42955PN
Show glycosyltransferases
There is only one chemically distinct structure:
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(later renamed to: Cryptococcus gattii VGI)