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Abstract:

Tin(IV) chloride-promoted condensation of benzyl 2-acetamido-3-O- benzoyl-2-deoxy-α-D-glucopyranoside (4) with penta-O-benzoyl-β-D- galactopyranose (6) gave the derivative of β-D-Galp-(1 → 6)-α-D-GlcNAc 7 in 80% yield. This was glycosylated with penta-O-benzoyl-α,β-D- galactofuranose (5), employing the same catalyst, to afford the protected benzyl per-O-benzoyl-β-D-Galf(1 → 4)[β-D-Galp(1 → 6)]D-GlcNAc 10 in 41% yield. Alternatively, compound 10 was obtained directly in a one-pot reaction from 4, by sequential addition of 6 and 5 (34% yield). β-Glycosidic linkages were diastereoselectively formed. De-O-benzoylation of 10, followed by heterogeneous catalytic transfer hydrogenolysis of the benzyl group afforded the free trisaccharide β-D-Galf(1 → 4)[ β-D-Galp(l → 6)]-D-GlcNAc (14) in 98% yield from 10. Sodium borohydride reduction of 14 gave the corresponding alditol, whose spectral data were identical to those reported for the alditol obtained from the 38-43 kDa cell-surface glycoprotein of Trypanosoma cruzi.

Registro:

Documento: Artículo
Título:One-pot synthesis of β-D-Galf(1 → 4)[β-D-Galp(1 → 6)]-D-GlcNac, a 'core' trisaccharide linked O-glycosidically in glycoproteins of Trypanosoma cruzi
Autor:Gallo-Rodriguez, C.; Varela, O.; De Lederkremer, R.M.
Filiación:CIHIDECAR, Depto. de Quimica Orgánica, Universidad de Buenos Aires, Buenos Aires 1428, Argentina
Palabras clave:Galactofuranose; Trisaccharide; Trypanosoma cruzi; glycoprotein; trisaccharide; article; carbohydrate analysis; carbohydrate synthesis; carbon nuclear magnetic resonance; glycoprotein synthesis; nonhuman; priority journal; protein analysis; protein glycosylation; trypanosoma cruzi; Animals; Carbohydrate Sequence; Glycoproteins; Molecular Sequence Data; Oxidation-Reduction; Protozoan Proteins; Sugar Alcohols; Trisaccharides; Trypanosoma cruzi; Trypanosoma; Trypanosoma cruzi
Año:1997
Volumen:305
Número:2
Página de inicio:163
Página de fin:170
DOI: http://dx.doi.org/10.1016/S0008-6215(97)00256-5
Título revista:Carbohydrate Research
Título revista abreviado:Carbohydr. Res.
ISSN:00086215
CODEN:CRBRA
CAS:Glycoproteins; Protozoan Proteins; Sugar Alcohols; Trisaccharides
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00086215_v305_n2_p163_GalloRodriguez

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Citas:

---------- APA ----------
Gallo-Rodriguez, C., Varela, O. & De Lederkremer, R.M. (1997) . One-pot synthesis of β-D-Galf(1 → 4)[β-D-Galp(1 → 6)]-D-GlcNac, a 'core' trisaccharide linked O-glycosidically in glycoproteins of Trypanosoma cruzi. Carbohydrate Research, 305(2), 163-170.
http://dx.doi.org/10.1016/S0008-6215(97)00256-5
---------- CHICAGO ----------
Gallo-Rodriguez, C., Varela, O., De Lederkremer, R.M. "One-pot synthesis of β-D-Galf(1 → 4)[β-D-Galp(1 → 6)]-D-GlcNac, a 'core' trisaccharide linked O-glycosidically in glycoproteins of Trypanosoma cruzi" . Carbohydrate Research 305, no. 2 (1997) : 163-170.
http://dx.doi.org/10.1016/S0008-6215(97)00256-5
---------- MLA ----------
Gallo-Rodriguez, C., Varela, O., De Lederkremer, R.M. "One-pot synthesis of β-D-Galf(1 → 4)[β-D-Galp(1 → 6)]-D-GlcNac, a 'core' trisaccharide linked O-glycosidically in glycoproteins of Trypanosoma cruzi" . Carbohydrate Research, vol. 305, no. 2, 1997, pp. 163-170.
http://dx.doi.org/10.1016/S0008-6215(97)00256-5
---------- VANCOUVER ----------
Gallo-Rodriguez, C., Varela, O., De Lederkremer, R.M. One-pot synthesis of β-D-Galf(1 → 4)[β-D-Galp(1 → 6)]-D-GlcNac, a 'core' trisaccharide linked O-glycosidically in glycoproteins of Trypanosoma cruzi. Carbohydr. Res. 1997;305(2):163-170.
http://dx.doi.org/10.1016/S0008-6215(97)00256-5