The glycosyl-aldonolactone approach for the synthesis of β-d-Galf-(1→3)-d-Manp and 3-deoxy-β-d-xylo-hexofuranosyl-(1→3)-d-Manp
A convenient synthesis of free β-d-Galf-(1→3)-d-Manp (8a) is reported. The disaccharide is present as external unit in the lipopeptidophosphoglycan (LPPG) of Trypanosoma cruzi and internally in the lipophosphoglycan (LPG) of Leishmania. Condensation of 2,5,6-tri-O-benzoyl-d-mannono-1,4-lactone (1) w...
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| Formato: | JOUR |
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| Acceso en línea: | http://hdl.handle.net/20.500.12110/paper_00086215_v311_n4_p183_Marino |
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todo:paper_00086215_v311_n4_p183_Marino2023-10-03T14:06:52Z The glycosyl-aldonolactone approach for the synthesis of β-d-Galf-(1→3)-d-Manp and 3-deoxy-β-d-xylo-hexofuranosyl-(1→3)-d-Manp Marino, C. Chiocconi, A. Varela, O. De Lederkremer, R.M. β-d-Galactofuranose disaccharides β-d-Galactofuranosidase Deoxy sugars Glycosyl-lactone Leishmania Trypanosoma cruzi carbohydrate derivative disaccharide lactone derivative article carbohydrate synthesis leishmania priority journal trypanosoma cruzi beta-Galactosidase Carbohydrate Sequence Disaccharides Glycoside Hydrolases Glycosphingolipids Magnetic Resonance Spectroscopy Models, Chemical Molecular Sequence Data Penicillium Substrate Specificity A convenient synthesis of free β-d-Galf-(1→3)-d-Manp (8a) is reported. The disaccharide is present as external unit in the lipopeptidophosphoglycan (LPPG) of Trypanosoma cruzi and internally in the lipophosphoglycan (LPG) of Leishmania. Condensation of 2,5,6-tri-O-benzoyl-d-mannono-1,4-lactone (1) with 1,2,3,5,6-penta-O-benzoyl-d-galactofuranose, promoted by SnCl4, led to the β-glycosyl-lactone, a key intermediate for disaccharide 8a, readily obtained by successive reduction of the lactone with diisoamylborane and debenzoylation. As in the LPG of Leishmania the HO-3 group of the galactofuranose is glycosylated by α-d-Galp, we also synthesized 3-deoxy-β-d-xylo-hexofuranosyl-(1→3)-d-Manp (8b) and p-nitrophenyl 3-deoxy-β-d-xylo-hexofuranoside for studying the influence of HO-3 in the interaction with specific glycosidases. The disaccharide 8a, and its corresponding alditol, were good substrates for the β-d-galactofuranosidase from Penicillium fellutanum, whereas the 3-deoxyglycosides were not hydrolyzed by the enzyme. Copyright (C) 1998 Elsevier Science Ltd. JOUR info:eu-repo/semantics/openAccess http://creativecommons.org/licenses/by/2.5/ar http://hdl.handle.net/20.500.12110/paper_00086215_v311_n4_p183_Marino |
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Universidad de Buenos Aires |
| institution_str |
I-28 |
| repository_str |
R-134 |
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Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) |
| topic |
β-d-Galactofuranose disaccharides β-d-Galactofuranosidase Deoxy sugars Glycosyl-lactone Leishmania Trypanosoma cruzi carbohydrate derivative disaccharide lactone derivative article carbohydrate synthesis leishmania priority journal trypanosoma cruzi beta-Galactosidase Carbohydrate Sequence Disaccharides Glycoside Hydrolases Glycosphingolipids Magnetic Resonance Spectroscopy Models, Chemical Molecular Sequence Data Penicillium Substrate Specificity |
| spellingShingle |
β-d-Galactofuranose disaccharides β-d-Galactofuranosidase Deoxy sugars Glycosyl-lactone Leishmania Trypanosoma cruzi carbohydrate derivative disaccharide lactone derivative article carbohydrate synthesis leishmania priority journal trypanosoma cruzi beta-Galactosidase Carbohydrate Sequence Disaccharides Glycoside Hydrolases Glycosphingolipids Magnetic Resonance Spectroscopy Models, Chemical Molecular Sequence Data Penicillium Substrate Specificity Marino, C. Chiocconi, A. Varela, O. De Lederkremer, R.M. The glycosyl-aldonolactone approach for the synthesis of β-d-Galf-(1→3)-d-Manp and 3-deoxy-β-d-xylo-hexofuranosyl-(1→3)-d-Manp |
| topic_facet |
β-d-Galactofuranose disaccharides β-d-Galactofuranosidase Deoxy sugars Glycosyl-lactone Leishmania Trypanosoma cruzi carbohydrate derivative disaccharide lactone derivative article carbohydrate synthesis leishmania priority journal trypanosoma cruzi beta-Galactosidase Carbohydrate Sequence Disaccharides Glycoside Hydrolases Glycosphingolipids Magnetic Resonance Spectroscopy Models, Chemical Molecular Sequence Data Penicillium Substrate Specificity |
| description |
A convenient synthesis of free β-d-Galf-(1→3)-d-Manp (8a) is reported. The disaccharide is present as external unit in the lipopeptidophosphoglycan (LPPG) of Trypanosoma cruzi and internally in the lipophosphoglycan (LPG) of Leishmania. Condensation of 2,5,6-tri-O-benzoyl-d-mannono-1,4-lactone (1) with 1,2,3,5,6-penta-O-benzoyl-d-galactofuranose, promoted by SnCl4, led to the β-glycosyl-lactone, a key intermediate for disaccharide 8a, readily obtained by successive reduction of the lactone with diisoamylborane and debenzoylation. As in the LPG of Leishmania the HO-3 group of the galactofuranose is glycosylated by α-d-Galp, we also synthesized 3-deoxy-β-d-xylo-hexofuranosyl-(1→3)-d-Manp (8b) and p-nitrophenyl 3-deoxy-β-d-xylo-hexofuranoside for studying the influence of HO-3 in the interaction with specific glycosidases. The disaccharide 8a, and its corresponding alditol, were good substrates for the β-d-galactofuranosidase from Penicillium fellutanum, whereas the 3-deoxyglycosides were not hydrolyzed by the enzyme. Copyright (C) 1998 Elsevier Science Ltd. |
| format |
JOUR |
| author |
Marino, C. Chiocconi, A. Varela, O. De Lederkremer, R.M. |
| author_facet |
Marino, C. Chiocconi, A. Varela, O. De Lederkremer, R.M. |
| author_sort |
Marino, C. |
| title |
The glycosyl-aldonolactone approach for the synthesis of β-d-Galf-(1→3)-d-Manp and 3-deoxy-β-d-xylo-hexofuranosyl-(1→3)-d-Manp |
| title_short |
The glycosyl-aldonolactone approach for the synthesis of β-d-Galf-(1→3)-d-Manp and 3-deoxy-β-d-xylo-hexofuranosyl-(1→3)-d-Manp |
| title_full |
The glycosyl-aldonolactone approach for the synthesis of β-d-Galf-(1→3)-d-Manp and 3-deoxy-β-d-xylo-hexofuranosyl-(1→3)-d-Manp |
| title_fullStr |
The glycosyl-aldonolactone approach for the synthesis of β-d-Galf-(1→3)-d-Manp and 3-deoxy-β-d-xylo-hexofuranosyl-(1→3)-d-Manp |
| title_full_unstemmed |
The glycosyl-aldonolactone approach for the synthesis of β-d-Galf-(1→3)-d-Manp and 3-deoxy-β-d-xylo-hexofuranosyl-(1→3)-d-Manp |
| title_sort |
glycosyl-aldonolactone approach for the synthesis of β-d-galf-(1→3)-d-manp and 3-deoxy-β-d-xylo-hexofuranosyl-(1→3)-d-manp |
| url |
http://hdl.handle.net/20.500.12110/paper_00086215_v311_n4_p183_Marino |
| work_keys_str_mv |
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| _version_ |
1807317042823430144 |