Selective sialylation of 2,3-di-O-(β-D-galactopyranosyl)-D-galactose catalyzed by Trypanosoma cruzi trans-sialidase

Trypanosoma cruzi, the agent of Chagas' disease, expresses on its surface a trans-sialidase (TcTS) that transfers sialic acid from host glycoconjugates to terminal β-galactopyranosyl units of parasite mucins. This process is involved in infection and pathogenesis. The trisaccharide 2,3-di-O-(β-...

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Autores principales:	Agusti, R., Mendoza, V.M., Gallo-Rodriguez, C., De Lederkremer, R.M.
Formato:	JOUR
Materias:	2,3 di o (beta dextro galactopyranosyl) dextro galactose alditol amine galactose glycoside protozoal protein sialic acid sialidase trisaccharide unclassified drug article carbon nuclear magnetic resonance catalysis chemical structure nuclear Overhauser effect priority journal proton nuclear magnetic resonance sialylation Trypanosoma cruzi
Acceso en línea:	http://hdl.handle.net/20.500.12110/paper_09574166_v16_n2_p541_Agusti
Aporte de:	Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) de Universidad de Buenos Aires

id	todo:paper_09574166_v16_n2_p541_Agusti
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spelling	todo:paper_09574166_v16_n2_p541_Agusti2023-10-03T15:52:24Z Selective sialylation of 2,3-di-O-(β-D-galactopyranosyl)-D-galactose catalyzed by Trypanosoma cruzi trans-sialidase Agusti, R. Mendoza, V.M. Gallo-Rodriguez, C. De Lederkremer, R.M. 2,3 di o (beta dextro galactopyranosyl) dextro galactose alditol amine galactose glycoside protozoal protein sialic acid sialidase trisaccharide unclassified drug article carbon nuclear magnetic resonance catalysis chemical structure nuclear Overhauser effect priority journal proton nuclear magnetic resonance sialylation Trypanosoma cruzi Trypanosoma cruzi, the agent of Chagas' disease, expresses on its surface a trans-sialidase (TcTS) that transfers sialic acid from host glycoconjugates to terminal β-galactopyranosyl units of parasite mucins. This process is involved in infection and pathogenesis. The trisaccharide 2,3-di-O-(β-d- galactopyranosyl)-d-galactose 1 is an external unit in the larger oligosaccharides of the mucins and a site for sialylation. The trisaccharide was previously synthesized in our laboratory. The last step of the synthesis was the hydrogenolysis of the crystalline benzyl trisaccharide. Herein we prove that the trisaccharide 1, its alditol 3 and the benzyl glycoside 2 are good acceptors of sialic acid and effective inhibitors of the sialylation of N-acetyllactosamine catalyzed by TcTS. Furthermore, selective sialylation of the 1→3 linked galactopyranose in glycoside 2 was determined by one and two-dimensional NMR analysis. In contrast, the flexible 2,3-di-O-(β-d- galactopyranosyl)-d-galactitol 3 is sialylated in either one of the two possible sites. © 2004 Elsevier Ltd. All rights reserved. JOUR info:eu-repo/semantics/openAccess http://creativecommons.org/licenses/by/2.5/ar http://hdl.handle.net/20.500.12110/paper_09574166_v16_n2_p541_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	2,3 di o (beta dextro galactopyranosyl) dextro galactose alditol amine galactose glycoside protozoal protein sialic acid sialidase trisaccharide unclassified drug article carbon nuclear magnetic resonance catalysis chemical structure nuclear Overhauser effect priority journal proton nuclear magnetic resonance sialylation Trypanosoma cruzi
spellingShingle	2,3 di o (beta dextro galactopyranosyl) dextro galactose alditol amine galactose glycoside protozoal protein sialic acid sialidase trisaccharide unclassified drug article carbon nuclear magnetic resonance catalysis chemical structure nuclear Overhauser effect priority journal proton nuclear magnetic resonance sialylation Trypanosoma cruzi Agusti, R. Mendoza, V.M. Gallo-Rodriguez, C. De Lederkremer, R.M. Selective sialylation of 2,3-di-O-(β-D-galactopyranosyl)-D-galactose catalyzed by Trypanosoma cruzi trans-sialidase
topic_facet	2,3 di o (beta dextro galactopyranosyl) dextro galactose alditol amine galactose glycoside protozoal protein sialic acid sialidase trisaccharide unclassified drug article carbon nuclear magnetic resonance catalysis chemical structure nuclear Overhauser effect priority journal proton nuclear magnetic resonance sialylation Trypanosoma cruzi
description	Trypanosoma cruzi, the agent of Chagas' disease, expresses on its surface a trans-sialidase (TcTS) that transfers sialic acid from host glycoconjugates to terminal β-galactopyranosyl units of parasite mucins. This process is involved in infection and pathogenesis. The trisaccharide 2,3-di-O-(β-d- galactopyranosyl)-d-galactose 1 is an external unit in the larger oligosaccharides of the mucins and a site for sialylation. The trisaccharide was previously synthesized in our laboratory. The last step of the synthesis was the hydrogenolysis of the crystalline benzyl trisaccharide. Herein we prove that the trisaccharide 1, its alditol 3 and the benzyl glycoside 2 are good acceptors of sialic acid and effective inhibitors of the sialylation of N-acetyllactosamine catalyzed by TcTS. Furthermore, selective sialylation of the 1→3 linked galactopyranose in glycoside 2 was determined by one and two-dimensional NMR analysis. In contrast, the flexible 2,3-di-O-(β-d- galactopyranosyl)-d-galactitol 3 is sialylated in either one of the two possible sites. © 2004 Elsevier Ltd. All rights reserved.
format	JOUR
author	Agusti, R. Mendoza, V.M. Gallo-Rodriguez, C. De Lederkremer, R.M.
author_facet	Agusti, R. Mendoza, V.M. Gallo-Rodriguez, C. De Lederkremer, R.M.
author_sort	Agusti, R.
title	Selective sialylation of 2,3-di-O-(β-D-galactopyranosyl)-D-galactose catalyzed by Trypanosoma cruzi trans-sialidase
title_short	Selective sialylation of 2,3-di-O-(β-D-galactopyranosyl)-D-galactose catalyzed by Trypanosoma cruzi trans-sialidase
title_full	Selective sialylation of 2,3-di-O-(β-D-galactopyranosyl)-D-galactose catalyzed by Trypanosoma cruzi trans-sialidase
title_fullStr	Selective sialylation of 2,3-di-O-(β-D-galactopyranosyl)-D-galactose catalyzed by Trypanosoma cruzi trans-sialidase
title_full_unstemmed	Selective sialylation of 2,3-di-O-(β-D-galactopyranosyl)-D-galactose catalyzed by Trypanosoma cruzi trans-sialidase
title_sort	selective sialylation of 2,3-di-o-(β-d-galactopyranosyl)-d-galactose catalyzed by trypanosoma cruzi trans-sialidase
url	http://hdl.handle.net/20.500.12110/paper_09574166_v16_n2_p541_Agusti
work_keys_str_mv	AT agustir selectivesialylationof23diobdgalactopyranosyldgalactosecatalyzedbytrypanosomacruzitranssialidase AT mendozavm selectivesialylationof23diobdgalactopyranosyldgalactosecatalyzedbytrypanosomacruzitranssialidase AT gallorodriguezc selectivesialylationof23diobdgalactopyranosyldgalactosecatalyzedbytrypanosomacruzitranssialidase AT delederkremerrm selectivesialylationof23diobdgalactopyranosyldgalactosecatalyzedbytrypanosomacruzitranssialidase
_version_	1807316498125946880

Selective sialylation of 2,3-di-O-(β-D-galactopyranosyl)-D-galactose catalyzed by Trypanosoma cruzi trans-sialidase

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