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1. (Article ID: 7121)
Simenel C, Coddeville B, Delepierre M, Latge JP, Fontaine T
Glycosylinositolphosphoceramides in Aspergillus Fumigatus
Glycobiology 18(1) (2008)
84-96
Fungal glycosylinositolphosphoceramides (GIPCs) are involved in cell growth and fungal–host interactions. In this study, six GIPCs from the mycelium of the human pathogen Aspergillus fumigatus were purified and characterized using Q-TOF mass spectrometry and 1H, 13C, and 31P NMR. All structures have the same inositolphosphoceramide moiety with the presence of a C18:0-phytosphingosine conjugated to a 2-hydroxylated saturated fatty acid (2-hydroxy-lignoceric acid). The carbohydrate moiety defines two types of GIPC. The first, a mannosylated zwitterionic glycosphingolipid contains a glucosamine residue linked in α1-2 to an inositol ring that has been described in only two other fungal pathogens. The second type of GIPC presents an α-Manp-(1→3)-α-Manp-(1→2)-IPC common core. A galactofuranose residue is found in four GIPC structures, mainly at the terminal position via a β1-2 linkage. Interestingly, this galactofuranose residue could be substituted by a choline–phosphate group, as observed only in the GIPC of Acremonium sp., a plant pathogen.
NMR, galactofuranose, glycosphingolipid, Aspergillus fumigatus, glycosylinositolphosphoceramide
Publication DOI: 10.1093/glycob/cwm122Journal NLM ID: 9104124Publisher: IRL Press at Oxford University Press
Correspondence: Thierry Fontaine
pasteur.fr>
Institutions: Unité des Aspergillus, Institut Pasteur, Paris, France, Unité de Résonance Magnétique Nucléaire des Biomolécules, CNRS URA 2185 Institut Pasteur, Paris, France, Unité de Glycobiologie Structurale et Fonctionnelle, UMR 8576 CNRS, Université des Sciences et Technologies de Lille, Villeneuve d’Ascq, France
Methods: 13C NMR, 1H NMR, methylation, GLC-MS, NMR-2D, 31P NMR, GLC, composition analysis, ion-exchange chromatography, extraction, HF treatment, 15N NMR, HPTLC, N-acetylation, nESI-QTOF-MS
The publication contains the following compound(s):
- Compound ID: 18028
|
2HOLig-(1-2)-+
|
a-Manp-(1-3)-a-Manp-(1-6)-a-GlcpN-(1-2)-L-myoIno-(1--P--1)--phSphC18 |
Show graphically |
Structure type: oligomer
Compound class: glycosphingolipid, glycosylinositolphosphoceramide
- Compound ID: 18171
|
2HOLig-(1-2)-+
|
b-Galf-(1-2)-a-Manp-(1-3)-a-Manp-(1-2)-L-myoIno-(1--P--1)--phSphC18
2HOLig = 2-hydroxylignoceric acid C24:0;
phSphC18 = phytosphingosine C18 |
Show graphically |
Structure type: oligomer
Compound class: glycosphingolipid, glycosylinositolphosphoceramide
- Compound ID: 18172
|
2HOLig-(1-2)-+
|
a-Manp-(1-3)-a-Manp-(1-2)-L-myoIno-(1--P--1)--phSphC18
2HOLig = 2-hydroxylignoceric acid C24:0;
phSphC18 = phytosphingosine C18 |
Show graphically |
Structure type: oligomer
Compound class: glycosphingolipid, glycosylinositolphosphoceramide
- Compound ID: 18173
|
a-Manp-(1-6)-+ 2HOLig-(1-2)-+
| |
b-Galf-(1-2)-a-Manp-(1-3)-a-Manp-(1-2)-L-myoIno-(1--P--1)--phSphC18
2HOLig = 2-hydroxylignoceric acid C24:0;
phSphC18 = phytosphingosine C18 |
Show graphically |
Structure type: oligomer
Compound class: glycosphingolipid, glycosylinositolphosphoceramide
- Compound ID: 18174
|
b-Galf-(1-6)-+ 2HOLig-(1-2)-+
| |
b-Galf-(1-2)-a-Manp-(1-3)-a-Manp-(1-2)-L-myoIno-(1--P--1)--phSphC18
2HOLig = 2-hydroxylignoceric acid C24:0;
phSphC18 = phytosphingosine C18 |
Show graphically |
Structure type: oligomer
Compound class: glycosphingolipid, glycosylinositolphosphoceramide
- Compound ID: 18175
|
2HOLig-(1-2)-+
|
Cho-(1--P--6)--b-Galf-(1-2)-a-Manp-(1-3)-a-Manp-(1-2)-L-myoIno-(1--P--1)--phSphC18
2HOLig = 2-hydroxylignoceric acid C24:0;
phSphC18 = phytosphingosine C18 |
Show graphically |
Structure type: oligomer
Compound class: glycosphingolipid, glycosylinositolphosphoceramide
- Compound ID: 18168
Structure type: oligomer
Compound class: glycosphingolipid, glycosylinositolphosphoceramide
- Compound ID: 18169
|
b-Galf-(1-6)-+
|
a-Manp-(1-3)-a-Manp-(1-2)-L-myoIno-(1--P--1)--CER |
Show graphically |
Structure type: oligomer
Compound class: glycosphingolipid, glycosylinositolphosphoceramide
- Compound ID: 18170
|
b-Galf-(1-6)-+
|
a-Manp-(1-2)-a-Manp-(1-3)-a-Manp-(1-2)-L-myoIno-(1--P--1)--CER |
Show graphically |
Structure type: oligomer
Compound class: glycosphingolipid, glycosylinositolphosphoceramide
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