Taxonomic group: fungi / Ascomycota
(Phylum: Ascomycota)
Associated disease: infection due to Aspergillus fumigatus [ICD11:
XN5Z7 
]
NCBI PubMed ID: 14659668Publication DOI: 10.1016/j.carres.2003.09.030Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: fzkong
mail.rcees.ac.cn
Institutions: Research Center for Eco-Environmental Sciences, Academia Sinica, P.O. Box 2871, Beijing 100085, China
Two oligosaccharides, α-d-Manp-(1→2)-α-d-Manp-(1→2)-α-d-Manp-(1→6)-α-d-Manp-(1→4)-α-d-GlcpNAc (I) and α-d-Manp-(1→3)-α-d-Manp-(1→2)-α-d-Manp-(1→2)-α-d-Manp-(1→6)-α-d-Manp-(1→4)-α-d-GlcpNAc (II), the glycosylphosphatidylinositol (GPI) anchor glycans from S. cerevesiae and A. fumigatus were synthesized as their methyl glycosides in a regio- and stereoselective manner. The pentasaccharide I was obtained from 6-O-selective glycosylation of methyl 2,3-di-O-benzoyl-α-d-mannopyranosyl-(1→4)-2-acetamido-3,6-di-O-benzoyl-2-deoxy-α-d-glucopyranoside (8) with 2-O-acetyl-3,4,6-tri-O-benzoyl-α-d-mannopyranosyl-(1→2)-3,4,6-tri-O-benzoyl-α-d-mannopyranosyl trichloroacetimidate (9), followed by benzoylation, deacetylation, and mannosylation, and then by deprotection. The hexasaccharide (II) was obtained via condensation of allyl 3,4,6-tri-O-benzoyl-α-d-mannopyranosyl-(1→2)-3,4,6-tri-O-benzoyl-α-d-mannopyranoside (17) with 2,3,4,6-tetra-O-benzoyl-α-d-mannopyranosyl-(1→3)-2,4,6-tri-O-acetyl-α-d-mannopyranosyl trichloroacetimidate (16), followed by deallylation, trichloroacetimidation, and coupling with acceptor (8), and finally by deprotection.
oligosaccharide, Mannose, Glucosamine, glucosamin
Structure type: oligomer
Location inside paper: p.29
Trivial name: GPI anchor glycan
Contained glycoepitopes: IEDB_130701,IEDB_136104,IEDB_140116,IEDB_141111,IEDB_141793,IEDB_141807,IEDB_141829,IEDB_141830,IEDB_141832,IEDB_143632,IEDB_144983,IEDB_151531,IEDB_152206,IEDB_153220,IEDB_164174,IEDB_164175,IEDB_164176,IEDB_174840,IEDB_76933,IEDB_983930,SB_136,SB_191,SB_196,SB_197,SB_198,SB_44,SB_67,SB_72
Methods: 13C NMR, 1H NMR, TLC, chemical synthesis, chemical methods, UV, glycosylation
Comments, role: synthesis of methylglycoside is described
Related record ID(s): 41217
NCBI Taxonomy refs (TaxIDs): 746128
Show glycosyltransferases
There is only one chemically distinct structure:
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