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Abstract:

The synthesis of α-D-Galp-(1→3)-β-D-Galf-(1→3)-D-Man, present in the type-2 glycoinositolphospholipids and in the core of the lipophosphoglycan of Leishmania, is described. The glycosyl aldonolactone approach, followed by reduction of the lactone with diisoamylborane, was utilized for the introduction of the internal galactofuranosyl unit and the trichloroacetimidate method for the O-glycosidation reaction. A high-yield synthesis of the β-D-Galf-(1-3)-D-Man unit, also present in the lipopeptidophosphoglycan of Trypanosoma cruzi, is reported.

Registro:

Documento: Artículo
Título:Synthesis of α-D-Galp-(1→3)-β-D-Galf-(1→3)-D-Man, a terminal trisaccharide of leishmania type-2 glycoinositolphospholipids
Autor:Gandolfi-Donadio, L.; Gallo-Rodriguez, C.; De Lederkremer, R.M.
Filiación:CIHIDECAR, Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Ciudad Universitaria, Pabellón II, 1428 Buenos Aires, Argentina
Palabras clave:Glycosidation; Reduction; Polysaccharides; alpha dextro galactopyranosyl (1-3) beta dextro galactofuranosyl (1-3) dextro mannose; beta dextro galactofuranosyl (1-3) dextro mannose; borane derivative; diisoamylborane; disaccharide; lactone; lipophosphoglycan; phosphatidylinositide; trichloroacetimidic acid; trisaccharide; unclassified drug; article; carbohydrate synthesis; chemical reaction; glycosylation; Leishmania; reduction; Trypanosoma cruzi; Animals; Carbohydrate Sequence; Catalysis; Chemistry, Organic; Chromatography, Thin Layer; Glycosphingolipids; Leishmania; Magnetic Resonance Spectroscopy; Molecular Sequence Data; Molecular Structure; Trisaccharides; Trypanosoma cruzi
Año:2002
Volumen:67
Número:13
Página de inicio:4430
Página de fin:4435
DOI: http://dx.doi.org/10.1021/jo016290z
Título revista:Journal of Organic Chemistry
Título revista abreviado:J. Org. Chem.
ISSN:00223263
CODEN:JOCEA
CAS:lactone, 1338-03-0; Galp-(1-3)-Galf-(1-3)-Man; Glycosphingolipids; Trisaccharides; lipophosphonoglycan
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00223263_v67_n13_p4430_GandolfiDonadio

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Citas:

---------- APA ----------
Gandolfi-Donadio, L., Gallo-Rodriguez, C. & De Lederkremer, R.M. (2002) . Synthesis of α-D-Galp-(1→3)-β-D-Galf-(1→3)-D-Man, a terminal trisaccharide of leishmania type-2 glycoinositolphospholipids. Journal of Organic Chemistry, 67(13), 4430-4435.
http://dx.doi.org/10.1021/jo016290z
---------- CHICAGO ----------
Gandolfi-Donadio, L., Gallo-Rodriguez, C., De Lederkremer, R.M. "Synthesis of α-D-Galp-(1→3)-β-D-Galf-(1→3)-D-Man, a terminal trisaccharide of leishmania type-2 glycoinositolphospholipids" . Journal of Organic Chemistry 67, no. 13 (2002) : 4430-4435.
http://dx.doi.org/10.1021/jo016290z
---------- MLA ----------
Gandolfi-Donadio, L., Gallo-Rodriguez, C., De Lederkremer, R.M. "Synthesis of α-D-Galp-(1→3)-β-D-Galf-(1→3)-D-Man, a terminal trisaccharide of leishmania type-2 glycoinositolphospholipids" . Journal of Organic Chemistry, vol. 67, no. 13, 2002, pp. 4430-4435.
http://dx.doi.org/10.1021/jo016290z
---------- VANCOUVER ----------
Gandolfi-Donadio, L., Gallo-Rodriguez, C., De Lederkremer, R.M. Synthesis of α-D-Galp-(1→3)-β-D-Galf-(1→3)-D-Man, a terminal trisaccharide of leishmania type-2 glycoinositolphospholipids. J. Org. Chem. 2002;67(13):4430-4435.
http://dx.doi.org/10.1021/jo016290z