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Sphingolipids of the mycopathogen Sporothrix schenckii : identification of a glycosylinositol phosphorylceramide with novel core GlcNH 2 α1→2Ins motif
Author(s) -
Toledo Marcos S.,
Levery Steven B.,
Straus Anita H.,
Takahashi Helio K.
Publication year - 2001
Publication title -
febs letters
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.593
H-Index - 257
eISSN - 1873-3468
pISSN - 0014-5793
DOI - 10.1016/s0014-5793(01)02275-x
Subject(s) - sporothrix schenckii , glycosphingolipid , electrospray ionization , chemistry , yeast , mass spectrometry , stereochemistry , glycan , nuclear magnetic resonance spectroscopy , biochemistry , chromatography , biology , glycoprotein , immunology , sporotrichosis
Acidic glycosphingolipid components were extracted from the yeast form of the dimorphic mycopathogen Sporothrix schenckii . Two minor and the major fraction from the yeast form (Ss‐Y1, ‐Y2, and ‐Y6, respectively) have been isolated. By a combination of 1‐ and 2‐D 1 H‐nuclear magnetic resonance (NMR) spectroscopy, electrospray ionization mass spectrometry (ESI‐MS), and gas chromatography/mass spectrometry (GC/MS), Ss‐Y6 was determined to be triglycosylinositol phosphorylceramide with a novel glycan structure, Manα1→3Manα1→6GlcNH 2 α1→2Ins1‐P‐1Cer (where Ins= myo ‐inositol, P=phosphodiester). While the GlcNH 2 α1→ 6 Ins1‐P‐ motif is found widely distributed in eukaryotic GPI anchors, the linkage GlcNH 2 α1→ 2 Ins1‐P‐ has not been previously observed in any glycolipid. Ss‐Y1 and Ss‐Y2 were both found to have the known glycan structure Manα1→3Manα1→2Ins1‐P‐1Cer. Together with the results of a prior study [Toledo et al. (2001) Biochem. Biophys. Res. Commun. 280, 19–24] which showed that the mycelium form expresses GIPCs with the structures Manα1→6Ins1‐P‐1Cer and Manα1→3Manα1→6Ins1‐P‐1Cer, these results demonstrate that S. schenckii can synthesize glycosylinositol phosphorylceramides with at least three different core linkages.