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Issue 31, 2012
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Synthesis of the O-linked hexasaccharide containing β-d-Galf-(1→2)-β-d-Galf in Trypanosoma cruzi mucins

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Abstract

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 1H NMR spectrum of alditol 2 was identical to the product released by β-elimination from the parasite mucin.

Graphical abstract: Synthesis of the O-linked hexasaccharide containing β-d-Galf-(1→2)-β-d-Galf in Trypanosoma cruzi mucins

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Publication details

The article was received on 17 Apr 2012, accepted on 11 Jun 2012 and first published on 13 Jun 2012


Article type: Paper
DOI: 10.1039/C2OB25741F
Org. Biomol. Chem., 2012,10, 6322-6332

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    Synthesis of the O-linked hexasaccharide containing β-D-Galf-(1→2)-β-D-Galf in Trypanosoma cruzi mucins

    G. A. Kashiwagi, V. M. Mendoza, R. M. de Lederkremer and C. Gallo-Rodriguez, Org. Biomol. Chem., 2012, 10, 6322
    DOI: 10.1039/C2OB25741F

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