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: 32932031Publication DOI: 10.1016/j.carres.2020.108150Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: conor.crawford
ucdconnect.ie
Institutions: Centre for Synthesis and Chemical Biology, University College Dublin, Dublin, Ireland
Cryptococcus neoformans is an opportunistic fungal pathogen, which is a frequent cause of a life-threatening meningitis in immunocompromised individuals. We report the first total synthesis of the serotype B heptasaccharide repeating motif. The use of di- and trisaccharide building blocks enabled a concise convergent synthesis of the protected 6-O-acetylated repeating motif in three steps. Glycosylations gave total 1,2-trans selectivity, despite the absence of a neighboring participating group. Using our recently disclosed catalyst pre-tuning strategy global deprotection gave the desired 6-O-acetylated heptasaccharide with no saturation by-products, overall in four steps 31% yield. The serotype B glucuronoxylomannan (GXM) glycans accessed in this study will increase the structurally diversity of our GXM microarray, allowing further steps towards the development of semi-synthetic vaccines against cryptococcal infections.
Thioglycoside, Glucuronoxylomannan, building block
Structure type: suggested polymer biological repeating unit
Location inside paper: Fig. 1
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: 13C NMR, 1H NMR, chemical synthesis, SEC, HR-ESI-MS, flash chromatography
Related record ID(s): 138, 9354, 40725, 40736, 40816, 41249, 42130, 42863, 43808, 43919, 49352, 49864, 136941, 148630
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)