Taxonomic group: fungi / Ascomycota
(Phylum: Ascomycota)
Associated disease: infection due to Aspergillus fumigatus [ICD11:
XN5Z7 
]
NCBI PubMed ID: 31007571Publication DOI: 10.1002/ejoc.201800894Journal NLM ID: 9805750Publisher: Wiley-VCH
Correspondence: jcodee
chem.leidenuniv.nl
Institutions: Leiden Institute of Chemistry, Leiden University, Leiden, The Netherlands
Pre-activation based glycosylations have become a very powerful tool in the assembly of oligosaccharides and the use of nucleophilic additives allows for the in situ generation of reactive intermediates with tailored reactivity. We here use a glycosylation strategy that is based on the use of per-benzylated imidate building blocks for the fully stereoselective construction of a spacer equipped Aspergillus fumigatus α-1,3-octaglucan. We have used the trimethylsilyl iodide (TMSI)-triphenylphosphine oxide (Ph3P=O) for the stereoselective installation of an azidopropanol spacer and triflic acid (TfOH)-dimethyl formamide (DMF) enabled glycosylations for the coupling reactions with the secondary glucosyl C-3-alcohols. An operationally simple in situ activation coupling procedure is introduced and used for the final glycosylation events towards the octasaccharide.
Oligosaccharides, glycosylation, stereoselectivity, α-1, 3-glucan, additive
Structure type: oligomer
Location inside paper: Scheme 2, 2
Trivial name: α-(1,3)-glucan
Compound class: glucan, oligosaccharide, α-(1, 3)-glucan
Contained glycoepitopes: IEDB_142488,IEDB_144998,IEDB_146664,IEDB_983931,SB_192
Methods: 13C NMR, 1H NMR, NMR-2D, IR, TLC, chemical synthesis, MALDI-TOF MS, optical rotation measurement, SEC, column chromatography, HR-ESI-MS
Synthetic data: chemical
NCBI Taxonomy refs (TaxIDs): 746128
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There is only one chemically distinct structure:
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