Taxonomic group: protista / Euglenozoa
(Phylum: Euglenozoa)
Host organism: Homo sapiens
Organ / tissue: cell surface,
Life stage: epimastigoteAssociated disease: Chagas disease [ICD11:
1F53 
, ICD11:
XN56V ];
infection due to Trypanosoma cruzi [ICD11:
XN56V ]
NCBI PubMed ID: 25703305Publication DOI: 10.1016/j.bmc.2015.01.056Journal NLM ID: 101154995Publisher: The Royal Society of Chemistry
Correspondence: R.M. de Lederkremer <lederk
qo.fcen.uba.ar>; 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 hexasaccharide β-D-Galp-(1→2)-[β-D-Galp-(1→3)]-β-D-Galp-(1→6)-[β-D-Galp(1→2)-β-D-Galf(1→4)]-D-GlcNAc (10) and its β-D-Galf-(1→2)-β-D-Galf containing isomer (7) are the largest carbohydrates in mucins of some strains of Trypanosoma cruzi. The terminal β-D-Galp units are sites of sialylation by the parasite trans-sialidase. Hexasaccharide 10 was chemically synthesized for the first time by a [3+3] nitrilium based convergent approach, using the trichloroacetimidate method of glycosylation. The (1)H NMR spectrum of its alditol was identical to the spectrum of the product released by β-elimination from the parasite mucin. The trans-sialylation reaction studied on the benzyl glycoside of 10 showed two monosialylated products whose relative abundance changed with time. On the other hand, only one product was produced by sialylation of the benzyl glycoside of 7. A preparative synthesis of the latter and spectroscopic analysis of the product unequivocally established the sialylation site at the less hindered (1→3)-linked galactopyranose.
Oligosaccharides, galactofuranose, glycosylation, Trypanosoma cruzi, mucins, Nitrilium, Parasite, trans-sialidase
Structure type: oligomer
Location inside paper: p. 1215, Fig. 2, compound 7
Trivial name: mucin oligosaccharide
Compound class: O-glycan
Contained glycoepitopes: IEDB_135813,IEDB_136044,IEDB_136095,IEDB_137340,IEDB_137472,IEDB_141794,IEDB_141807,IEDB_151531,IEDB_190606,IEDB_241097,SB_165,SB_166,SB_187,SB_195,SB_7,SB_88
Methods: 13C NMR, 1H NMR, TLC, HPAEC, chemical synthesis, HPAEC-PAD, sialylation, ESI-TOF-MS
Related record ID(s): 5435, 5436, 5437, 5438, 7253, 7394, 7395, 7396, 7397, 7399
NCBI Taxonomy refs (TaxIDs): 5693
Show glycosyltransferases
There is only one chemically distinct structure:
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