Synthesis of the O-linked hexasaccharide containing β-d-Galp-(1→2)-d-Galf in Trypanosoma cruzi mucins. Differences on sialylation by trans-sialidase of the two constituent hexasaccharides

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 th...

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Autores principales:	Agustí, Rosalía, Giorgi, María Eugenia, Mendoza, Verónica María, Muchnik de Lederkremer, Rosa María, Gallo, Carola
Publicado:	2015
Materias:	Galactofuranose Glycosylation Mucins trans-Sialidase Nitrilium Oligosaccharides Trypanosoma cruzi beta dextro galactofuranosyl (1-2) beta dextro galactofuranosyl beta dextro galactopyranosyl (1-2) [beta dextro galactopyranosyl (1-3)] beta dextro galactopyranosyl (1-6) [beta dextro galactopyranosyl (1-2) beta dextro galactofuranosyl (1-4)] 2 acetamido 2 deoxy alpha,beta dextro glucopyranose beta dextro galactopyranosyl (1-2) [beta dextro galactopyranosyl (1-3)] beta dextro galactopyranosyl (1-6) [beta dextro galactopyranosyl (1-2) beta dextro galactofuranosyl (1-4)] 2 acetamido 2 deoxy dextro glucitol beta dextro galactopyranosyl (1-2) [beta dextro galactopyranosyl (1-3)] beta dextro galactopyranosyl (1-6) [beta dextro galactopyranosyl (1-2) beta dextro galactofuranosyl (1-4)] dextro n acetylglutamic acid carbohydrate derivative glycoside trichloroacetimidic acid unclassified drug glycoprotein mucin oligosaccharide sialidase trans-sialidase Article carbohydrate analysis carbohydrate synthesis enzyme kinetics enzyme structure glycosylation nonhuman proton nuclear magnetic resonance sialylation spectroscopy chemistry conformation metabolism molecular genetics synthesis Carbohydrate Conformation Carbohydrate Sequence Glycoproteins Molecular Sequence Data Mucins Neuraminidase
Acceso en línea:	https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_09680896_v23_n6_p1213_Agusti http://hdl.handle.net/20.500.12110/paper_09680896_v23_n6_p1213_Agusti
Aporte de:	Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) de Universidad de Buenos Aires

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spelling	paper:paper_09680896_v23_n6_p1213_Agusti2023-06-08T15:58:57Z Synthesis of the O-linked hexasaccharide containing β-d-Galp-(1→2)-d-Galf in Trypanosoma cruzi mucins. Differences on sialylation by trans-sialidase of the two constituent hexasaccharides Agustí, Rosalía Giorgi, María Eugenia Mendoza, Verónica María Muchnik de Lederkremer, Rosa María Gallo, Carola Galactofuranose Glycosylation Mucins trans-Sialidase Nitrilium Oligosaccharides Trypanosoma cruzi beta dextro galactofuranosyl (1-2) beta dextro galactofuranosyl beta dextro galactopyranosyl (1-2) [beta dextro galactopyranosyl (1-3)] beta dextro galactopyranosyl (1-6) [beta dextro galactopyranosyl (1-2) beta dextro galactofuranosyl (1-4)] 2 acetamido 2 deoxy alpha,beta dextro glucopyranose beta dextro galactopyranosyl (1-2) [beta dextro galactopyranosyl (1-3)] beta dextro galactopyranosyl (1-6) [beta dextro galactopyranosyl (1-2) beta dextro galactofuranosyl (1-4)] 2 acetamido 2 deoxy dextro glucitol beta dextro galactopyranosyl (1-2) [beta dextro galactopyranosyl (1-3)] beta dextro galactopyranosyl (1-6) [beta dextro galactopyranosyl (1-2) beta dextro galactofuranosyl (1-4)] dextro n acetylglutamic acid carbohydrate derivative glycoside trichloroacetimidic acid unclassified drug glycoprotein mucin oligosaccharide sialidase trans-sialidase Article carbohydrate analysis carbohydrate synthesis enzyme kinetics enzyme structure glycosylation nonhuman proton nuclear magnetic resonance sialylation spectroscopy Trypanosoma cruzi chemistry conformation metabolism molecular genetics synthesis Trypanosoma cruzi Trypanosoma cruzi Carbohydrate Conformation Carbohydrate Sequence Glycoproteins Molecular Sequence Data Mucins Neuraminidase Oligosaccharides Trypanosoma cruzi 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 1H 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. © 2015 Elsevier Ltd. All rights reserved. Fil:Agustí, R. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:Giorgi, M.E. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:Mendoza, V.M. 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. Fil:Gallo-Rodriguez, C. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. 2015 https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_09680896_v23_n6_p1213_Agusti http://hdl.handle.net/20.500.12110/paper_09680896_v23_n6_p1213_Agusti
institution	Universidad de Buenos Aires
institution_str	I-28
repository_str	R-134
collection	Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA)
topic	Galactofuranose Glycosylation Mucins trans-Sialidase Nitrilium Oligosaccharides Trypanosoma cruzi beta dextro galactofuranosyl (1-2) beta dextro galactofuranosyl beta dextro galactopyranosyl (1-2) [beta dextro galactopyranosyl (1-3)] beta dextro galactopyranosyl (1-6) [beta dextro galactopyranosyl (1-2) beta dextro galactofuranosyl (1-4)] 2 acetamido 2 deoxy alpha,beta dextro glucopyranose beta dextro galactopyranosyl (1-2) [beta dextro galactopyranosyl (1-3)] beta dextro galactopyranosyl (1-6) [beta dextro galactopyranosyl (1-2) beta dextro galactofuranosyl (1-4)] 2 acetamido 2 deoxy dextro glucitol beta dextro galactopyranosyl (1-2) [beta dextro galactopyranosyl (1-3)] beta dextro galactopyranosyl (1-6) [beta dextro galactopyranosyl (1-2) beta dextro galactofuranosyl (1-4)] dextro n acetylglutamic acid carbohydrate derivative glycoside trichloroacetimidic acid unclassified drug glycoprotein mucin oligosaccharide sialidase trans-sialidase Article carbohydrate analysis carbohydrate synthesis enzyme kinetics enzyme structure glycosylation nonhuman proton nuclear magnetic resonance sialylation spectroscopy Trypanosoma cruzi chemistry conformation metabolism molecular genetics synthesis Trypanosoma cruzi Trypanosoma cruzi Carbohydrate Conformation Carbohydrate Sequence Glycoproteins Molecular Sequence Data Mucins Neuraminidase Oligosaccharides Trypanosoma cruzi
spellingShingle	Galactofuranose Glycosylation Mucins trans-Sialidase Nitrilium Oligosaccharides Trypanosoma cruzi beta dextro galactofuranosyl (1-2) beta dextro galactofuranosyl beta dextro galactopyranosyl (1-2) [beta dextro galactopyranosyl (1-3)] beta dextro galactopyranosyl (1-6) [beta dextro galactopyranosyl (1-2) beta dextro galactofuranosyl (1-4)] 2 acetamido 2 deoxy alpha,beta dextro glucopyranose beta dextro galactopyranosyl (1-2) [beta dextro galactopyranosyl (1-3)] beta dextro galactopyranosyl (1-6) [beta dextro galactopyranosyl (1-2) beta dextro galactofuranosyl (1-4)] 2 acetamido 2 deoxy dextro glucitol beta dextro galactopyranosyl (1-2) [beta dextro galactopyranosyl (1-3)] beta dextro galactopyranosyl (1-6) [beta dextro galactopyranosyl (1-2) beta dextro galactofuranosyl (1-4)] dextro n acetylglutamic acid carbohydrate derivative glycoside trichloroacetimidic acid unclassified drug glycoprotein mucin oligosaccharide sialidase trans-sialidase Article carbohydrate analysis carbohydrate synthesis enzyme kinetics enzyme structure glycosylation nonhuman proton nuclear magnetic resonance sialylation spectroscopy Trypanosoma cruzi chemistry conformation metabolism molecular genetics synthesis Trypanosoma cruzi Trypanosoma cruzi Carbohydrate Conformation Carbohydrate Sequence Glycoproteins Molecular Sequence Data Mucins Neuraminidase Oligosaccharides Trypanosoma cruzi Agustí, Rosalía Giorgi, María Eugenia Mendoza, Verónica María Muchnik de Lederkremer, Rosa María Gallo, Carola Synthesis of the O-linked hexasaccharide containing β-d-Galp-(1→2)-d-Galf in Trypanosoma cruzi mucins. Differences on sialylation by trans-sialidase of the two constituent hexasaccharides
topic_facet	Galactofuranose Glycosylation Mucins trans-Sialidase Nitrilium Oligosaccharides Trypanosoma cruzi beta dextro galactofuranosyl (1-2) beta dextro galactofuranosyl beta dextro galactopyranosyl (1-2) [beta dextro galactopyranosyl (1-3)] beta dextro galactopyranosyl (1-6) [beta dextro galactopyranosyl (1-2) beta dextro galactofuranosyl (1-4)] 2 acetamido 2 deoxy alpha,beta dextro glucopyranose beta dextro galactopyranosyl (1-2) [beta dextro galactopyranosyl (1-3)] beta dextro galactopyranosyl (1-6) [beta dextro galactopyranosyl (1-2) beta dextro galactofuranosyl (1-4)] 2 acetamido 2 deoxy dextro glucitol beta dextro galactopyranosyl (1-2) [beta dextro galactopyranosyl (1-3)] beta dextro galactopyranosyl (1-6) [beta dextro galactopyranosyl (1-2) beta dextro galactofuranosyl (1-4)] dextro n acetylglutamic acid carbohydrate derivative glycoside trichloroacetimidic acid unclassified drug glycoprotein mucin oligosaccharide sialidase trans-sialidase Article carbohydrate analysis carbohydrate synthesis enzyme kinetics enzyme structure glycosylation nonhuman proton nuclear magnetic resonance sialylation spectroscopy Trypanosoma cruzi chemistry conformation metabolism molecular genetics synthesis Trypanosoma cruzi Trypanosoma cruzi Carbohydrate Conformation Carbohydrate Sequence Glycoproteins Molecular Sequence Data Mucins Neuraminidase Oligosaccharides Trypanosoma cruzi
description	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 1H 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. © 2015 Elsevier Ltd. All rights reserved.
author	Agustí, Rosalía Giorgi, María Eugenia Mendoza, Verónica María Muchnik de Lederkremer, Rosa María Gallo, Carola
author_facet	Agustí, Rosalía Giorgi, María Eugenia Mendoza, Verónica María Muchnik de Lederkremer, Rosa María Gallo, Carola
author_sort	Agustí, Rosalía
title	Synthesis of the O-linked hexasaccharide containing β-d-Galp-(1→2)-d-Galf in Trypanosoma cruzi mucins. Differences on sialylation by trans-sialidase of the two constituent hexasaccharides
title_short	Synthesis of the O-linked hexasaccharide containing β-d-Galp-(1→2)-d-Galf in Trypanosoma cruzi mucins. Differences on sialylation by trans-sialidase of the two constituent hexasaccharides
title_full	Synthesis of the O-linked hexasaccharide containing β-d-Galp-(1→2)-d-Galf in Trypanosoma cruzi mucins. Differences on sialylation by trans-sialidase of the two constituent hexasaccharides
title_fullStr	Synthesis of the O-linked hexasaccharide containing β-d-Galp-(1→2)-d-Galf in Trypanosoma cruzi mucins. Differences on sialylation by trans-sialidase of the two constituent hexasaccharides
title_full_unstemmed	Synthesis of the O-linked hexasaccharide containing β-d-Galp-(1→2)-d-Galf in Trypanosoma cruzi mucins. Differences on sialylation by trans-sialidase of the two constituent hexasaccharides
title_sort	synthesis of the o-linked hexasaccharide containing β-d-galp-(1→2)-d-galf in trypanosoma cruzi mucins. differences on sialylation by trans-sialidase of the two constituent hexasaccharides
publishDate	2015
url	https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_09680896_v23_n6_p1213_Agusti http://hdl.handle.net/20.500.12110/paper_09680896_v23_n6_p1213_Agusti
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_version_	1768544328777465856

Synthesis of the O-linked hexasaccharide containing β-d-Galp-(1→2)-d-Galf in Trypanosoma cruzi mucins. Differences on sialylation by trans-sialidase of the two constituent hexasaccharides

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