Synthesis of 2,3-di-O-(β-D-Galp)-D-Galp, a synthon for the mucinoligosaccharides of Trypanosoma cruzi

The synthesis of an anomeric free derivative of 2,3-di-O-(β-D-Galp)-D- Galp as a synthon for the mucin oligosaccharides of Trypanosoma cruzi is described. The title compound was synthesized via two approaches. The first one involved 2,3-di-O-glycosylation of 5,6-O-isopropylidene-D-galactono-1,4-lact...

Descripción completa

Detalles Bibliográficos
Autores principales:	Mendoza, V.M., Gallo-Rodriguez, C., De Lederkremer, R.M.
Formato:	JOUR
Materias:	D-galactono-1,4-lactone Galactose trisaccharide Glycosylation Mucins Trichloroacetimidate Trypanosoma cruzi 2,3 di o (2,3,4,6 tetra o acetyl beta dextro galactopyranosyl) 5,6 o isopropylidene dextro galactono 1,4 lactone 2,3 di o beta dextro galactopyranosyl beta dextro galactopyranoside 4,6 di o acetyl 2,3 di o (2,3,4,6 tetra o acetyl beta dextro galactopyranosyl) dextro galactopyranose carbohydrate derivative chemical compound galactopyranose lactone derivative mucin o (2,3,4,6 tetra o acetyl alpha dextro galactopyranosyl)trichloroacetimidate oligosaccharide sialic acid sialidase trisaccharide unclassified drug article chemical reaction glycosylation isomerization synthesis
Acceso en línea:	http://hdl.handle.net/20.500.12110/paper_14246376_v2003_n10_p82_Mendoza
Aporte de:	Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) de Universidad de Buenos Aires

id	todo:paper_14246376_v2003_n10_p82_Mendoza
record_format	dspace
spelling	todo:paper_14246376_v2003_n10_p82_Mendoza2023-10-03T16:13:38Z Synthesis of 2,3-di-O-(β-D-Galp)-D-Galp, a synthon for the mucinoligosaccharides of Trypanosoma cruzi Mendoza, V.M. Gallo-Rodriguez, C. De Lederkremer, R.M. D-galactono-1,4-lactone Galactose trisaccharide Glycosylation Mucins Trichloroacetimidate Trypanosoma cruzi 2,3 di o (2,3,4,6 tetra o acetyl beta dextro galactopyranosyl) 5,6 o isopropylidene dextro galactono 1,4 lactone 2,3 di o beta dextro galactopyranosyl beta dextro galactopyranoside 4,6 di o acetyl 2,3 di o (2,3,4,6 tetra o acetyl beta dextro galactopyranosyl) dextro galactopyranose carbohydrate derivative chemical compound galactopyranose lactone derivative mucin o (2,3,4,6 tetra o acetyl alpha dextro galactopyranosyl)trichloroacetimidate oligosaccharide sialic acid sialidase trisaccharide unclassified drug article chemical reaction glycosylation isomerization synthesis Trypanosoma cruzi The synthesis of an anomeric free derivative of 2,3-di-O-(β-D-Galp)-D- Galp as a synthon for the mucin oligosaccharides of Trypanosoma cruzi is described. The title compound was synthesized via two approaches. The first one involved 2,3-di-O-glycosylation of 5,6-O-isopropylidene-D-galactono-1,4-lactone by O-(2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl) trichloroacetimidate. The second approach was based on glycosylation of a convenient derivative of galactopyranose. The synthesized trisaccharide is the acceptor unit of sialic acid in the trans-sialidase reaction that takes place in T. cruzi. JOUR info:eu-repo/semantics/openAccess http://creativecommons.org/licenses/by/2.5/ar http://hdl.handle.net/20.500.12110/paper_14246376_v2003_n10_p82_Mendoza
institution	Universidad de Buenos Aires
institution_str	I-28
repository_str	R-134
collection	Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA)
topic	D-galactono-1,4-lactone Galactose trisaccharide Glycosylation Mucins Trichloroacetimidate Trypanosoma cruzi 2,3 di o (2,3,4,6 tetra o acetyl beta dextro galactopyranosyl) 5,6 o isopropylidene dextro galactono 1,4 lactone 2,3 di o beta dextro galactopyranosyl beta dextro galactopyranoside 4,6 di o acetyl 2,3 di o (2,3,4,6 tetra o acetyl beta dextro galactopyranosyl) dextro galactopyranose carbohydrate derivative chemical compound galactopyranose lactone derivative mucin o (2,3,4,6 tetra o acetyl alpha dextro galactopyranosyl)trichloroacetimidate oligosaccharide sialic acid sialidase trisaccharide unclassified drug article chemical reaction glycosylation isomerization synthesis Trypanosoma cruzi
spellingShingle	D-galactono-1,4-lactone Galactose trisaccharide Glycosylation Mucins Trichloroacetimidate Trypanosoma cruzi 2,3 di o (2,3,4,6 tetra o acetyl beta dextro galactopyranosyl) 5,6 o isopropylidene dextro galactono 1,4 lactone 2,3 di o beta dextro galactopyranosyl beta dextro galactopyranoside 4,6 di o acetyl 2,3 di o (2,3,4,6 tetra o acetyl beta dextro galactopyranosyl) dextro galactopyranose carbohydrate derivative chemical compound galactopyranose lactone derivative mucin o (2,3,4,6 tetra o acetyl alpha dextro galactopyranosyl)trichloroacetimidate oligosaccharide sialic acid sialidase trisaccharide unclassified drug article chemical reaction glycosylation isomerization synthesis Trypanosoma cruzi Mendoza, V.M. Gallo-Rodriguez, C. De Lederkremer, R.M. Synthesis of 2,3-di-O-(β-D-Galp)-D-Galp, a synthon for the mucinoligosaccharides of Trypanosoma cruzi
topic_facet	D-galactono-1,4-lactone Galactose trisaccharide Glycosylation Mucins Trichloroacetimidate Trypanosoma cruzi 2,3 di o (2,3,4,6 tetra o acetyl beta dextro galactopyranosyl) 5,6 o isopropylidene dextro galactono 1,4 lactone 2,3 di o beta dextro galactopyranosyl beta dextro galactopyranoside 4,6 di o acetyl 2,3 di o (2,3,4,6 tetra o acetyl beta dextro galactopyranosyl) dextro galactopyranose carbohydrate derivative chemical compound galactopyranose lactone derivative mucin o (2,3,4,6 tetra o acetyl alpha dextro galactopyranosyl)trichloroacetimidate oligosaccharide sialic acid sialidase trisaccharide unclassified drug article chemical reaction glycosylation isomerization synthesis Trypanosoma cruzi
description	The synthesis of an anomeric free derivative of 2,3-di-O-(β-D-Galp)-D- Galp as a synthon for the mucin oligosaccharides of Trypanosoma cruzi is described. The title compound was synthesized via two approaches. The first one involved 2,3-di-O-glycosylation of 5,6-O-isopropylidene-D-galactono-1,4-lactone by O-(2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl) trichloroacetimidate. The second approach was based on glycosylation of a convenient derivative of galactopyranose. The synthesized trisaccharide is the acceptor unit of sialic acid in the trans-sialidase reaction that takes place in T. cruzi.
format	JOUR
author	Mendoza, V.M. Gallo-Rodriguez, C. De Lederkremer, R.M.
author_facet	Mendoza, V.M. Gallo-Rodriguez, C. De Lederkremer, R.M.
author_sort	Mendoza, V.M.
title	Synthesis of 2,3-di-O-(β-D-Galp)-D-Galp, a synthon for the mucinoligosaccharides of Trypanosoma cruzi
title_short	Synthesis of 2,3-di-O-(β-D-Galp)-D-Galp, a synthon for the mucinoligosaccharides of Trypanosoma cruzi
title_full	Synthesis of 2,3-di-O-(β-D-Galp)-D-Galp, a synthon for the mucinoligosaccharides of Trypanosoma cruzi
title_fullStr	Synthesis of 2,3-di-O-(β-D-Galp)-D-Galp, a synthon for the mucinoligosaccharides of Trypanosoma cruzi
title_full_unstemmed	Synthesis of 2,3-di-O-(β-D-Galp)-D-Galp, a synthon for the mucinoligosaccharides of Trypanosoma cruzi
title_sort	synthesis of 2,3-di-o-(β-d-galp)-d-galp, a synthon for the mucinoligosaccharides of trypanosoma cruzi
url	http://hdl.handle.net/20.500.12110/paper_14246376_v2003_n10_p82_Mendoza
work_keys_str_mv	AT mendozavm synthesisof23diobdgalpdgalpasynthonforthemucinoligosaccharidesoftrypanosomacruzi AT gallorodriguezc synthesisof23diobdgalpdgalpasynthonforthemucinoligosaccharidesoftrypanosomacruzi AT delederkremerrm synthesisof23diobdgalpdgalpasynthonforthemucinoligosaccharidesoftrypanosomacruzi
_version_	1807317074588991488

Synthesis of 2,3-di-O-(β-D-Galp)-D-Galp, a synthon for the mucinoligosaccharides of Trypanosoma cruzi

Ejemplares similares