Taxonomic group: protista / Euglenozoa
(Phylum: Euglenozoa)
Host organism: (mammal)
Associated disease: Chagas disease [ICD11:
1F53 
, ICD11:
XN56V ];
infection due to Trypanosoma cruzi [ICD11:
XN56V ]
NCBI PubMed ID: 20044082Publication DOI: 10.1016/j.carres.2009.12.005Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: C. Gallo-Rodriguez <cgallo
qo.fcen.uba.ar>
Institutions: CIHIDECAR, Departamento de Quimica Organica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Ciudad Universitaria, Pabellon II, 1428 Buenos Aires, Argentina
The trisaccharides β-d-Galf-(1→2)-β-d-Galf-(1→4)-d-GlcNAc (5) and β-d-Galp-(1→2)-β-d-Galf-(1→4)-d-GlcNAc (6) constitute novel structures isolated as alditols when released by reductive β-elimination from mucins of Trypanosoma cruzi (Tulahuen strain). Trisaccharides 5 and 6 were synthesized employing the aldonolactone approach. Thus, a convenient d-galactono-1,4-lactone derivative was used for the introduction of the internal galactofuranose and the trichloroacetimidate method was employed for glycosylation reactions. Due to the lack of anchimeric assistance on O-2 of the galactofuranosyl precursor, glycosylation studies were performed under different conditions. The nature of the solvent strongly determined the stereochemical course of the glycosylation reactions when the galactofuranosyl donor was substituted either by 2-O-Galp or 2-O-Galf.
trisaccharide, galactofuranose, glycosylation, Trypanosoma cruzi, Galactonolactone, Mucin, Trichloroacetimidate glycosylation
Structure type: oligomer
Location inside paper: p. 386, Fig. 1, compound 2
Aglycon: (1->3)Thr/Ser
Trivial name: mucin-like glycan (group I)
Compound class: O-glycan
Contained glycoepitopes: IEDB_135813,IEDB_136044,IEDB_136095,IEDB_137340,IEDB_137472,IEDB_141794,IEDB_141807,IEDB_151531,IEDB_190606,SB_165,SB_166,SB_187,SB_195,SB_7,SB_88
Methods: 13C NMR, 1H NMR, NMR-2D, TLC, chemical synthesis, chemical methods, UV, glycosylation, HR-MS, optical rotation measuremen
Related record ID(s): 7336, 8194, 8195, 8196, 8197, 8198, 8199, 8200, 8201, 8202
NCBI Taxonomy refs (TaxIDs): 5693,
1416333
Show glycosyltransferases
There is only one chemically distinct structure:
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