Synthesis of 4-nitrophenyl β-D-fucofuranoside and β-D-fucofuranosyl-(1 → 3)-D-mannopyranose: Modified substrates for studies on catalytic requirements of β-D-galactofuranosidase
Syntheses of 4-nitrophenyl β-D-fucofuranoside (6) and β-D- fucofuranosyl-(1 → 3)-D-mannopyranose (10) are reported. These compounds, as analogues of galactofuranosides, were used for studying the influence of the hydroxyl group at C-6 in the interaction of the substrate with β-D- galactofuranosidase...
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todo:paper_00086215_v323_n1-4_p7_Chiocconi2023-10-03T14:06:54Z Synthesis of 4-nitrophenyl β-D-fucofuranoside and β-D-fucofuranosyl-(1 → 3)-D-mannopyranose: Modified substrates for studies on catalytic requirements of β-D-galactofuranosidase Chiocconi, A. Marino, C. De Lederkremer, R.M. β-D-Fucofuranosides Deoxy sugars Exo β-D-Galactofuranosidase article carbohydrate analysis carbohydrate synthesis chemical reaction enzyme substrate complex nonhuman Penicillium priority journal Alcohols beta-Galactosidase Catalysis Disaccharides Fucose Glycoside Hydrolases Magnetic Resonance Spectroscopy Models, Chemical Nitrobenzenes Penicillium Substrate Specificity Temperature Syntheses of 4-nitrophenyl β-D-fucofuranoside (6) and β-D- fucofuranosyl-(1 → 3)-D-mannopyranose (10) are reported. These compounds, as analogues of galactofuranosides, were used for studying the influence of the hydroxyl group at C-6 in the interaction of the substrate with β-D- galactofuranosidase. For the synthesis of the fucofuranosides, 2,3,5-tri-O- benzoyl-6-bromo-6-deoxy-D-galactono-1,4-lactone (1) was the key intermediate, which upon reduction of the lactone group with diisoamylborane, acetylation of the anomeric hydroxyl group, and catalytic hydrogenolysis of the bromine at C-6, led to 1-O-acetyl-2,3,5-tri-O-benzoyl-α,β-D-fucofuranose (4), a convenient derivative for the preparation of fucofuranosides. Compound 4 was glycosylated in the presence of SnCl4, either with 4-nitrophenol for the preparation of 6, or with 2,5,6-tri-O-benzoyl-D-mannono-1,4-lactone (7), for the synthesis of disaccharide 10, via the glycosyl-aldonolactone approach. The synthetic route developed for the β-D-fucofuranosides is simple and efficient. Compound 6 was not hydrolyzed by incubation with the exo β-D- galactofuranosidase from Penicillium fellutanum, showing that HO-6 is essential for interaction of the substrate with the enzyme. (C) 2000 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_v323_n1-4_p7_Chiocconi |
| institution |
Universidad de Buenos Aires |
| institution_str |
I-28 |
| repository_str |
R-134 |
| collection |
Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) |
| topic |
β-D-Fucofuranosides Deoxy sugars Exo β-D-Galactofuranosidase article carbohydrate analysis carbohydrate synthesis chemical reaction enzyme substrate complex nonhuman Penicillium priority journal Alcohols beta-Galactosidase Catalysis Disaccharides Fucose Glycoside Hydrolases Magnetic Resonance Spectroscopy Models, Chemical Nitrobenzenes Penicillium Substrate Specificity Temperature |
| spellingShingle |
β-D-Fucofuranosides Deoxy sugars Exo β-D-Galactofuranosidase article carbohydrate analysis carbohydrate synthesis chemical reaction enzyme substrate complex nonhuman Penicillium priority journal Alcohols beta-Galactosidase Catalysis Disaccharides Fucose Glycoside Hydrolases Magnetic Resonance Spectroscopy Models, Chemical Nitrobenzenes Penicillium Substrate Specificity Temperature Chiocconi, A. Marino, C. De Lederkremer, R.M. Synthesis of 4-nitrophenyl β-D-fucofuranoside and β-D-fucofuranosyl-(1 → 3)-D-mannopyranose: Modified substrates for studies on catalytic requirements of β-D-galactofuranosidase |
| topic_facet |
β-D-Fucofuranosides Deoxy sugars Exo β-D-Galactofuranosidase article carbohydrate analysis carbohydrate synthesis chemical reaction enzyme substrate complex nonhuman Penicillium priority journal Alcohols beta-Galactosidase Catalysis Disaccharides Fucose Glycoside Hydrolases Magnetic Resonance Spectroscopy Models, Chemical Nitrobenzenes Penicillium Substrate Specificity Temperature |
| description |
Syntheses of 4-nitrophenyl β-D-fucofuranoside (6) and β-D- fucofuranosyl-(1 → 3)-D-mannopyranose (10) are reported. These compounds, as analogues of galactofuranosides, were used for studying the influence of the hydroxyl group at C-6 in the interaction of the substrate with β-D- galactofuranosidase. For the synthesis of the fucofuranosides, 2,3,5-tri-O- benzoyl-6-bromo-6-deoxy-D-galactono-1,4-lactone (1) was the key intermediate, which upon reduction of the lactone group with diisoamylborane, acetylation of the anomeric hydroxyl group, and catalytic hydrogenolysis of the bromine at C-6, led to 1-O-acetyl-2,3,5-tri-O-benzoyl-α,β-D-fucofuranose (4), a convenient derivative for the preparation of fucofuranosides. Compound 4 was glycosylated in the presence of SnCl4, either with 4-nitrophenol for the preparation of 6, or with 2,5,6-tri-O-benzoyl-D-mannono-1,4-lactone (7), for the synthesis of disaccharide 10, via the glycosyl-aldonolactone approach. The synthetic route developed for the β-D-fucofuranosides is simple and efficient. Compound 6 was not hydrolyzed by incubation with the exo β-D- galactofuranosidase from Penicillium fellutanum, showing that HO-6 is essential for interaction of the substrate with the enzyme. (C) 2000 Elsevier Science Ltd. |
| format |
JOUR |
| author |
Chiocconi, A. Marino, C. De Lederkremer, R.M. |
| author_facet |
Chiocconi, A. Marino, C. De Lederkremer, R.M. |
| author_sort |
Chiocconi, A. |
| title |
Synthesis of 4-nitrophenyl β-D-fucofuranoside and β-D-fucofuranosyl-(1 → 3)-D-mannopyranose: Modified substrates for studies on catalytic requirements of β-D-galactofuranosidase |
| title_short |
Synthesis of 4-nitrophenyl β-D-fucofuranoside and β-D-fucofuranosyl-(1 → 3)-D-mannopyranose: Modified substrates for studies on catalytic requirements of β-D-galactofuranosidase |
| title_full |
Synthesis of 4-nitrophenyl β-D-fucofuranoside and β-D-fucofuranosyl-(1 → 3)-D-mannopyranose: Modified substrates for studies on catalytic requirements of β-D-galactofuranosidase |
| title_fullStr |
Synthesis of 4-nitrophenyl β-D-fucofuranoside and β-D-fucofuranosyl-(1 → 3)-D-mannopyranose: Modified substrates for studies on catalytic requirements of β-D-galactofuranosidase |
| title_full_unstemmed |
Synthesis of 4-nitrophenyl β-D-fucofuranoside and β-D-fucofuranosyl-(1 → 3)-D-mannopyranose: Modified substrates for studies on catalytic requirements of β-D-galactofuranosidase |
| title_sort |
synthesis of 4-nitrophenyl β-d-fucofuranoside and β-d-fucofuranosyl-(1 → 3)-d-mannopyranose: modified substrates for studies on catalytic requirements of β-d-galactofuranosidase |
| url |
http://hdl.handle.net/20.500.12110/paper_00086215_v323_n1-4_p7_Chiocconi |
| work_keys_str_mv |
AT chiocconia synthesisof4nitrophenylbdfucofuranosideandbdfucofuranosyl13dmannopyranosemodifiedsubstratesforstudiesoncatalyticrequirementsofbdgalactofuranosidase AT marinoc synthesisof4nitrophenylbdfucofuranosideandbdfucofuranosyl13dmannopyranosemodifiedsubstratesforstudiesoncatalyticrequirementsofbdgalactofuranosidase AT delederkremerrm synthesisof4nitrophenylbdfucofuranosideandbdfucofuranosyl13dmannopyranosemodifiedsubstratesforstudiesoncatalyticrequirementsofbdgalactofuranosidase |
| _version_ |
1807316402395152384 |