Synthesis of the O-linked pentasaccharide in glycoproteins of Trypanosoma cruzi and selective sialylation by recombinant trans-sialidase
The mucin-like glycoproteins of Trypanosoma cruzi have novel O-linked oligosaccharides that are acceptors of sialic acid in the trans-sialidase (TcTS) reaction. The transference of sialic acid from host glycoconjugates to the mucins is involved in infection and pathogenesis. The synthesis of the pen...
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todo:paper_00086215_v341_n10_p1488_Mendoza2023-10-03T14:07:09Z Synthesis of the O-linked pentasaccharide in glycoproteins of Trypanosoma cruzi and selective sialylation by recombinant trans-sialidase Mendoza, V.M. Agusti, R. Gallo-Rodriguez, C. de Lederkremer, R.M. Galactofuranose Pentasaccharide Sialic acid trans-Sialidase Trichloroacetimidate glycosylation Trypanosoma cruzi Nuclear magnetic resonance Organic acids Proteins Reaction kinetics Reduction Synthesis (chemical) Galactofuranose Pentasaccharides Sialic acid trans-Sialidase Trichloroacetimidate glycosylation Trypanosoma cruzi Saccharification alditol glycoconjugate glycoprotein mucin nitrile oligosaccharide pentasaccharide sialic acid sialidase trichloroacetimidic acid article carbohydrate synthesis elimination reaction glycosylation isolation procedure nonhuman nuclear magnetic resonance spectroscopy priority journal sialylation stereochemistry Trypanosoma cruzi Animals Carbohydrate Sequence Glycoproteins Molecular Sequence Data Mucins Neuraminidase Nuclear Magnetic Resonance, Biomolecular Oligosaccharides Recombinant Proteins Trypanosoma cruzi Trypanosoma cruzi The mucin-like glycoproteins of Trypanosoma cruzi have novel O-linked oligosaccharides that are acceptors of sialic acid in the trans-sialidase (TcTS) reaction. The transference of sialic acid from host glycoconjugates to the mucins is involved in infection and pathogenesis. The synthesis of the pentasaccharide, β-d-Galp-(1→2)-[β-d-Galp-(1→3)]-β-d-Galp-(1→6)-[β-d-Galf-(1→4)]-d-GlcpNAc and the corresponding alditol, previously isolated by reductive β-elimination of the mucins, is described. The key step was the 6-O-glycosylation of a easily accessible derivative of β-d-Galf-(1→4)-d-GlcpNAc with a β-d-Galp-(1→2)-[β-d-Galp-(1→3)]-d-Galp donor using the trichloroacetimidate method. The β-linkage was diastereoselectively obtained by the nitrile effect. The pentasaccharide is the major oligosaccharide in the mucins of T. cruzi, G strain and presents two terminal β-d-Galp residues for possible sialylation by TcTS. A preparative sialylation reaction was performed with its benzyl glycoside and the sialylated product was isolated and characterized. NMR spectroscopic analysis showed that selective monosialylation occurred at the terminal (1→3) linked galactopyranose. © 2006 Elsevier Ltd. All rights reserved. Fil:Mendoza, V.M. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:Agusti, R. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:Gallo-Rodriguez, C. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:de Lederkremer, R.M. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. JOUR info:eu-repo/semantics/openAccess http://creativecommons.org/licenses/by/2.5/ar http://hdl.handle.net/20.500.12110/paper_00086215_v341_n10_p1488_Mendoza |
| institution |
Universidad de Buenos Aires |
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I-28 |
| repository_str |
R-134 |
| collection |
Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) |
| topic |
Galactofuranose Pentasaccharide Sialic acid trans-Sialidase Trichloroacetimidate glycosylation Trypanosoma cruzi Nuclear magnetic resonance Organic acids Proteins Reaction kinetics Reduction Synthesis (chemical) Galactofuranose Pentasaccharides Sialic acid trans-Sialidase Trichloroacetimidate glycosylation Trypanosoma cruzi Saccharification alditol glycoconjugate glycoprotein mucin nitrile oligosaccharide pentasaccharide sialic acid sialidase trichloroacetimidic acid article carbohydrate synthesis elimination reaction glycosylation isolation procedure nonhuman nuclear magnetic resonance spectroscopy priority journal sialylation stereochemistry Trypanosoma cruzi Animals Carbohydrate Sequence Glycoproteins Molecular Sequence Data Mucins Neuraminidase Nuclear Magnetic Resonance, Biomolecular Oligosaccharides Recombinant Proteins Trypanosoma cruzi Trypanosoma cruzi |
| spellingShingle |
Galactofuranose Pentasaccharide Sialic acid trans-Sialidase Trichloroacetimidate glycosylation Trypanosoma cruzi Nuclear magnetic resonance Organic acids Proteins Reaction kinetics Reduction Synthesis (chemical) Galactofuranose Pentasaccharides Sialic acid trans-Sialidase Trichloroacetimidate glycosylation Trypanosoma cruzi Saccharification alditol glycoconjugate glycoprotein mucin nitrile oligosaccharide pentasaccharide sialic acid sialidase trichloroacetimidic acid article carbohydrate synthesis elimination reaction glycosylation isolation procedure nonhuman nuclear magnetic resonance spectroscopy priority journal sialylation stereochemistry Trypanosoma cruzi Animals Carbohydrate Sequence Glycoproteins Molecular Sequence Data Mucins Neuraminidase Nuclear Magnetic Resonance, Biomolecular Oligosaccharides Recombinant Proteins Trypanosoma cruzi Trypanosoma cruzi Mendoza, V.M. Agusti, R. Gallo-Rodriguez, C. de Lederkremer, R.M. Synthesis of the O-linked pentasaccharide in glycoproteins of Trypanosoma cruzi and selective sialylation by recombinant trans-sialidase |
| topic_facet |
Galactofuranose Pentasaccharide Sialic acid trans-Sialidase Trichloroacetimidate glycosylation Trypanosoma cruzi Nuclear magnetic resonance Organic acids Proteins Reaction kinetics Reduction Synthesis (chemical) Galactofuranose Pentasaccharides Sialic acid trans-Sialidase Trichloroacetimidate glycosylation Trypanosoma cruzi Saccharification alditol glycoconjugate glycoprotein mucin nitrile oligosaccharide pentasaccharide sialic acid sialidase trichloroacetimidic acid article carbohydrate synthesis elimination reaction glycosylation isolation procedure nonhuman nuclear magnetic resonance spectroscopy priority journal sialylation stereochemistry Trypanosoma cruzi Animals Carbohydrate Sequence Glycoproteins Molecular Sequence Data Mucins Neuraminidase Nuclear Magnetic Resonance, Biomolecular Oligosaccharides Recombinant Proteins Trypanosoma cruzi Trypanosoma cruzi |
| description |
The mucin-like glycoproteins of Trypanosoma cruzi have novel O-linked oligosaccharides that are acceptors of sialic acid in the trans-sialidase (TcTS) reaction. The transference of sialic acid from host glycoconjugates to the mucins is involved in infection and pathogenesis. The synthesis of the pentasaccharide, β-d-Galp-(1→2)-[β-d-Galp-(1→3)]-β-d-Galp-(1→6)-[β-d-Galf-(1→4)]-d-GlcpNAc and the corresponding alditol, previously isolated by reductive β-elimination of the mucins, is described. The key step was the 6-O-glycosylation of a easily accessible derivative of β-d-Galf-(1→4)-d-GlcpNAc with a β-d-Galp-(1→2)-[β-d-Galp-(1→3)]-d-Galp donor using the trichloroacetimidate method. The β-linkage was diastereoselectively obtained by the nitrile effect. The pentasaccharide is the major oligosaccharide in the mucins of T. cruzi, G strain and presents two terminal β-d-Galp residues for possible sialylation by TcTS. A preparative sialylation reaction was performed with its benzyl glycoside and the sialylated product was isolated and characterized. NMR spectroscopic analysis showed that selective monosialylation occurred at the terminal (1→3) linked galactopyranose. © 2006 Elsevier Ltd. All rights reserved. |
| format |
JOUR |
| author |
Mendoza, V.M. Agusti, R. Gallo-Rodriguez, C. de Lederkremer, R.M. |
| author_facet |
Mendoza, V.M. Agusti, R. Gallo-Rodriguez, C. de Lederkremer, R.M. |
| author_sort |
Mendoza, V.M. |
| title |
Synthesis of the O-linked pentasaccharide in glycoproteins of Trypanosoma cruzi and selective sialylation by recombinant trans-sialidase |
| title_short |
Synthesis of the O-linked pentasaccharide in glycoproteins of Trypanosoma cruzi and selective sialylation by recombinant trans-sialidase |
| title_full |
Synthesis of the O-linked pentasaccharide in glycoproteins of Trypanosoma cruzi and selective sialylation by recombinant trans-sialidase |
| title_fullStr |
Synthesis of the O-linked pentasaccharide in glycoproteins of Trypanosoma cruzi and selective sialylation by recombinant trans-sialidase |
| title_full_unstemmed |
Synthesis of the O-linked pentasaccharide in glycoproteins of Trypanosoma cruzi and selective sialylation by recombinant trans-sialidase |
| title_sort |
synthesis of the o-linked pentasaccharide in glycoproteins of trypanosoma cruzi and selective sialylation by recombinant trans-sialidase |
| url |
http://hdl.handle.net/20.500.12110/paper_00086215_v341_n10_p1488_Mendoza |
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