Taxonomic group: protista / Euglenozoa
(Phylum: Euglenozoa)
Host organism: (mammal)
Associated disease: animal trypanosomiasis (Nagana disease) [ICD11:
XN9H4 
]
Publication DOI: 10.1039/c2sc21515bJournal NLM ID: 101545951Publisher: Cambridge, UK: Royal Society of Chemistry
Correspondence: seeberger
mpikg.mpg.de; daniel.varon
mpikg.mpg.de
Institutions: Department of Biomolecular Systems, Max Planck Institute of Colloids and Interfaces, Am Mühlenberg 1, 14476 Potsdam, Germany, Institute of Chemistry and Biochemistry, Free University of Berlin, Arnimallee 22, 14195 Berlin, Germany
Glycosylphosphatidylinositol (GPI) glycolipids anchor a large number of proteins in the cell membrane of eukaryotic cells. Their conserved pseudopentasaccharide core carries additional phosphoethanolamine, saccharide and lipid substituents. These structural variations are characteristic for a species or a tissue but their functional significance remains largely unknown. Studies that would link a specific function to a structurally unique GPI rely on availability of homogeneous samples of these glycolipids. To address this need we have developed a general synthetic route to GPI glycolipids. Our convergent synthesis starts from common building blocks and relies on a fully orthogonal set of protecting groups that enables the regioselective introduction of phosphodiesters and efficient assembly of the GPI glycans. Here, we report on the development of this synthetic strategy, evaluation of the set of protecting groups with respect to phosphorylation methods, evaluation of the assembly plan for the GPI glycan, optimization of the glycosylation reactions, and the application of this strategy to the total syntheses of four structurally diverse branched GPI glycolipids.
synthesis, glycosylation, glycolipids, glycans, Glycosylphosphatidylinositol, GPI
Structure type: oligomer
Location inside paper: p. 469, Fig. 1, scheme 5, T. congolense, compound 42
Trivial name: variant surface glycoproteins (VSG) GPI anchor 4
Compound class: GPI-anchor
Contained glycoepitopes: IEDB_120354,IEDB_123890,IEDB_130701,IEDB_135813,IEDB_136044,IEDB_136104,IEDB_137340,IEDB_137472,IEDB_140116,IEDB_141793,IEDB_141794,IEDB_141807,IEDB_141829,IEDB_143632,IEDB_144983,IEDB_151531,IEDB_152206,IEDB_153220,IEDB_176772,IEDB_190606,IEDB_474450,IEDB_983930,SB_136,SB_165,SB_166,SB_187,SB_191,SB_195,SB_196,SB_198,SB_44,SB_67,SB_7,SB_72,SB_88
Synthetic data: chemical
Comments, role: review
NCBI Taxonomy refs (TaxIDs): 5692
Show glycosyltransferases
There is only one chemically distinct structure:
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