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 ]
The structure was elucidated in this paperNCBI PubMed ID: 22735493Publication DOI: 10.1039/c2ob25741fJournal NLM ID: 101154995Publisher: The Royal Society of Chemistry
Correspondence: 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-Galf(1→2)-β-D-Galf(1→4)]-D-GlcNAc (1) is the largest carbohydrate structure released as alditol by reductive β-elimination from mucins of some strains of T. cruzi. The terminal β-D-Galp units are sites of sialylation by trans-sialidase which transfers sialic acid from the host to the parasite. Hexasaccharide 1 was synthesized by a [3 + 3]-convergent strategy based on a nitrile assisted glycosylation, using the trichloroacetimidate method. The β-D-Galf-(1→2)-β-D-Galf-D-GlcNAc synthon was sequentially constructed from the reducing end to the non-reducing end employing benzyl α-D-galactofuranoside as starting material for the internal Galf unit. The choice of this novel precursor, obtained in one-reaction step from galactose, allowed the introduction of an orthogonal and participating levulinoyl group at O-2. Thus, the diastereoselective construction of the Galf-β(1→4)-GlcNAc linkage by the trichloroacetimidate method of glycosylation was achieved. The (1)H NMR spectrum of alditol 2 was identical to the product released by β-elimination from the parasite mucin.
NMR, synthesis, sialic acid, glycosylation, Trypanosoma cruzi, mucins, Parasite, trans-sialidase
Structure type: oligomer ; 1054.3402 [M+Na]+
C
38H
64NO
30Location inside paper: abstract, p. 6323, Fig.1, compound 1
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, NMR-2D, TLC, chemical synthesis, glycosylation, optical rotation measurement, CC, HR-MS
Synthetic data: chemical
NCBI Taxonomy refs (TaxIDs): 5693
Show glycosyltransferases
There is only one chemically distinct structure:
Found 
report error