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Taxonomic group: fungi / Basidiomycota (Phylum: Basidiomycota)
Associated disease: infection due to Cryptococcus neoformans [ICD11: XN3EH

]

Publication DOI: 10.1046/j.1432-1327.2001.02339.x
Journal NLM ID: 0107600
Publisher: Oxford, UK: Blackwell Science Ltd. on behalf of the Federation of European Biochemical Societies
Correspondence: immglup

microbio.ufrj.br
Institutions: Departamento de Biologia Celular e Genética and Departamento de Bioquímica, UERJ, Rio de Janeiro, Brasil, Kennedy Institute for Rheumatology, Imperial College, London, UK, Laboratory for Molecular Structure, NIBSC, Herts, UK, Instituto de Microbiologia, CCS-Bloco I, Universidade Federal do Rio de Janeiro, Rio de Janeiro, Brasil

Novel structures of glycoinositolphosphorylceramide (GIPC) from the infective yeast form of Sporothrix schenckii were determined by methylation analysis, mass spectrometry and NMR spectroscopy. The lipid portion was characterized as a ceramide composed of C-18 phytosphingosine N-acylated by either 2-hydroxylignoceric acid (80%), lignoceric (15%) or 2,3-dihydroxylignoceric acids (5%). The ceramide was linked through a phosphodiester to myo-inositol (Ins) which is substituted on position O-6 by an oligomannose chain. GIPC-derived Ins oligomannosides were liberated by ammonolysis and characterized as: Manp-α1→6Ins; Manp-α1→3Manp-α1→6Ins; Manp-α1→6Manp-α1→3Manp-α1→3Manp-α1→6Ins; Manp-α1→2Manp-α1→6Manp-α1→3Manp-α1→3Manp-α1→6Ins. These structures comprise a novel family of fungal GIPC, as they contain the Manp-α1→6Ins substructure, which has not previously been characterized unambigously, and may be acylated with a 2,3-dihydroxylignoceric fatty acid, a feature hitherto undescribed in fungal lipids.

NMR, mass spectrometry, Sporothrix schenckii, glycoinositolphosphorylceramide

Structure type: oligomer
Location inside paper: table 2
Contained glycoepitopes: IEDB_114701,IEDB_130701,IEDB_136044,IEDB_136104,IEDB_137472,IEDB_1394182,IEDB_140116,IEDB_141793,IEDB_141794,IEDB_141828,IEDB_141829,IEDB_141831,IEDB_143632,IEDB_144983,IEDB_145668,IEDB_152206,IEDB_153220,IEDB_164174,IEDB_167188,IEDB_174332,IEDB_190606,IEDB_76933,IEDB_983930,SB_136,SB_165,SB_166,SB_187,SB_191,SB_195,SB_196,SB_197,SB_198,SB_44,SB_67,SB_7,SB_72,SB_88

Methods: 13C NMR, 1H NMR, gel filtration, GC-MS, GLC, MALDI-MS, HPLC, TOCSY, methylation analysis, HMBC, HMQC, NOESY, ammonolysis
Comments, role: part of glycoinositolphosphorylceramide

Related record ID(s): 40466, 40661, 40662, 40663, 40664, 40665, 40666, 40667, 40668, 40669, 40670, 40671, 40672, 40673
NCBI Taxonomy refs (TaxIDs): 5207
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There are 256 chemically distinct structures. Please, select:

OC[C@H]1O[C@H](O[C@@H]2[C@@H](OC[C@H]3O[C@H](OC[C@H]4O[C@H](O[C@H]5[C@H](O)[C@@H](CO)O[C@H](O[C@@H]6[C@H](O)[C@@H](O)[C@H](OC[C@H]7O[C@H](O[C@@H]8[C@H](O)[C@@H](O)[C@H](O)[C@@H](O)[C@@H]8O)[C@@H](O)[C@@H](O)[C@@H]7O)O[C@@H]6CO)[C@H]5O[C@@H]5OC[C@@H](O)[C@H](O)[C@H]5O)[C@@H](O)[C@@H](O)[C@@H]4O)[C@@H](O)[C@@H](O)[C@@H]3O)O[C@H](CO)[C@@H](O)[C@@H]2O)[C@@H](O)[C@@H](O)[C@@H]1O

SVG MW SMILES 3D mol Ionize