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
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...
Guardado en:
| Autores principales: | , , |
|---|---|
| Formato: | JOUR |
| Materias: | |
| Acceso en línea: | http://hdl.handle.net/20.500.12110/paper_00086215_v305_n2_p163_GalloRodriguez |
| Aporte de: |
| id |
todo:paper_00086215_v305_n2_p163_GalloRodriguez |
|---|---|
| record_format |
dspace |
| spelling |
todo:paper_00086215_v305_n2_p163_GalloRodriguez2023-10-03T14:06:51Z 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 Gallo-Rodriguez, C. Varela, O. De Lederkremer, R.M. 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 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. JOUR info:eu-repo/semantics/openAccess http://creativecommons.org/licenses/by/2.5/ar http://hdl.handle.net/20.500.12110/paper_00086215_v305_n2_p163_GalloRodriguez |
| 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 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 |
| spellingShingle |
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 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 |
| topic_facet |
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 |
| description |
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. |
| format |
JOUR |
| author |
Gallo-Rodriguez, C. Varela, O. De Lederkremer, R.M. |
| author_facet |
Gallo-Rodriguez, C. Varela, O. De Lederkremer, R.M. |
| author_sort |
Gallo-Rodriguez, C. |
| title |
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 |
| title_short |
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 |
| title_full |
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 |
| title_fullStr |
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 |
| title_full_unstemmed |
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 |
| title_sort |
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 |
| url |
http://hdl.handle.net/20.500.12110/paper_00086215_v305_n2_p163_GalloRodriguez |
| work_keys_str_mv |
AT gallorodriguezc onepotsynthesisofbdgalf14bdgalp16dglcnacacoretrisaccharidelinkedoglycosidicallyinglycoproteinsoftrypanosomacruzi AT varelao onepotsynthesisofbdgalf14bdgalp16dglcnacacoretrisaccharidelinkedoglycosidicallyinglycoproteinsoftrypanosomacruzi AT delederkremerrm onepotsynthesisofbdgalf14bdgalp16dglcnacacoretrisaccharidelinkedoglycosidicallyinglycoproteinsoftrypanosomacruzi |
| _version_ |
1807319976961376256 |