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Taxonomic group: protista / Euglenozoa (Phylum: Euglenozoa)
Host organism: Homo sapiens
Associated disease: Chagas disease [ICD11: 1F53

, ICD11: XN56V

]; infection due to Trypanosoma cruzi [ICD11: XN56V

]

NCBI PubMed ID: 26660677
Publication DOI: 10.1039/c5cc07694c
Journal NLM ID: 9610838
Publisher: Cambridge: Royal Society of Chemistry
Correspondence: daniel.varon

mpikg.mpg.de
Institutions: Max Planck Institute of Colloids and Interfaces, Biomolecular Systems, Am Mühlenberg 1, 14476 Potsdam, Germany

2-Naphthyl-methyl ethers as permanent protecting groups are readily removed under acidic conditions and are key to the synthesis of complex glycosylphosphatidylinositol anchors containing unsaturated lipids. The total synthesis of the GPI pseudo-disaccharide core found on the surface of the Trypanosoma cruzi parasite serves to illustrate the power of the strategy.

synthesis, glycolipids, Trypanosoma cruzi, Glycosylphosphatidylinositol, GPI

Structure type: oligomer
Location inside paper: p. 1586, Fig. 1, compound 1
Compound class: GPI-anchor
Contained glycoepitopes: IEDB_120354,IEDB_123890,IEDB_130701,IEDB_136104,IEDB_140116,IEDB_141793,IEDB_141807,IEDB_141829,IEDB_141830,IEDB_141832,IEDB_143632,IEDB_144983,IEDB_151531,IEDB_152206,IEDB_153220,IEDB_474450,IEDB_76933,IEDB_983930,SB_136,SB_191,SB_196,SB_198,SB_44,SB_67,SB_72

Methods: chemical synthesis, chemical methods, phosphorylation
Comments, role: ALK = C18:0;

NCBI Taxonomy refs (TaxIDs): 5693
Show glycosyltransferases

There is only one chemically distinct structure:

$[1*]OCC(COP(=O)(O)O[C@H]1[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O[C@H]1O[C@H](COP(=O)(O)CCN)[C@@H](O[C@H]2O[C@H](CO[C@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]3O[C@H]3O[C@H](COP(=O)(O)OCCN[2*])[C@@H](O)[C@H](O)[C@@H]3O[C@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]3O)[C@@H](O)[C@H](O)[C@@H]2O)[C@H](O)[C@H]1N)OC(=O)CCCCCCC/C=C\C/C=C\CCCCC$

SVG MW SMILES 3D mol Ionize

R1 = ALK
R2 = protein