Taxonomic group: protista / Euglenozoa
(Phylum: Euglenozoa)
Host organism: (mammal)
Organ / tissue: Life stage: trypomastigoteAssociated disease: Chagas disease [ICD11:
1F53 
, ICD11:
XN56V ];
infection due to Trypanosoma cruzi [ICD11:
XN56V ]
NCBI PubMed ID: 35775947Publication DOI: 10.1021/acs.joc.2c01059Journal NLM ID: 2985193RPublisher: Columbus, OH: American Chemical Society
Correspondence: L. Uhrig <mluhrig
qo.fcen.uba.ar>; R. Agusti <ragusti
qo.fcen.uba.ar>
Institutions: Departamento de Química Orgánica, Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales, C1428EGA Buenos Aires, Argentina, Centro de Investigaciones en Hidratos de Carbono (CIHIDECAR), CONICET- Universidad de Buenos Aires, C1428EGA Buenos Aires, Argentina
Two important activities take place in the surface of Trypanosoma cruzi, the agent of Chagas disease: the trans-sialidase (TcTS) catalyzes the transfer of sialic acid from the host glycoconjugates to the mucin-like glycoproteins from the parasite and the presence of lytic antibodies recognize the epitope α-Galp(1→3)-β-Galp(1→4)-α-GlcNAcp. This antigenic structure is known to be present in the parasite mucins; however, in order to be substrates of trans-sialidase, some of the galactose residues should be in the β-Galp configuration. To study the interaction between both activities, it is important to count the synthetic structures as well as the structural-related glycomimetics. With this purpose, we addressed the synthesis of a trisaccharide and two isomeric tetrasaccharides containing the 1-S-α-Galp(1→3)-β-Galp motif, the thio analog of the epitope recognized by lytic antibodies. Starting with a common lactose precursor, the sulfur function was incorporated by double inversion of the configuration of the galactose residue that was further glycosylated using different activated donors. Both tetrasaccharides were good acceptors of sialic acid in the reaction catalyzed by TcTS, as determined by high-performance anion exchange chromatography.
NMR, synthesis, Trypanosoma cruzi, trans-sialidase (TcTS)
Structure type: oligomer
Location inside paper: p. 13455, abstract
Trivial name: α-gal epitope, mucin oligosaccharide, α-gal epitope
Compound class: O-glycan
Contained glycoepitopes: IEDB_115013,IEDB_130645,IEDB_130649,IEDB_135815,IEDB_136044,IEDB_136906,IEDB_137340,IEDB_137472,IEDB_140108,IEDB_141496,IEDB_141794,IEDB_141807,IEDB_149558,IEDB_151528,IEDB_151531,IEDB_190606,IEDB_418918,IEDB_918314,SB_165,SB_166,SB_187,SB_195,SB_30,SB_7,SB_87,SB_88
Methods: 13C NMR, 1H NMR, NMR-2D, IR, TLC, HPAEC, chemical synthesis, chemical methods, UV, CC, HR-ESI-MS
NCBI Taxonomy refs (TaxIDs): 5693
Show glycosyltransferases
There is only one chemically distinct structure:
Found 
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