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Abstract:

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.

Registro:

Documento: Artículo
Título: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
Autor:Chiocconi, A.; Marino, C.; De Lederkremer, R.M.
Filiación:CIHIDECAR, Depto. Quim. Organ., Fac. Cie. E., Buenos Aires, Argentina
Palabras clave: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
Año:1999
Volumen:323
Número:1-4
Página de inicio:7
Página de fin:13
DOI: http://dx.doi.org/10.1016/S0008-6215(99)00241-4
Título revista:Carbohydrate Research
Título revista abreviado:Carbohydr. Res.
ISSN:00086215
CODEN:CRBRA
CAS:4-nitrophenyl fucofuranoside; Alcohols; beta-Galactosidase, EC 3.2.1.23; Disaccharides; exo-beta-D-galactofuranosidase, EC 3.2.1.-; fucofuranosyl-1-3-mannopyranose; Fucose, 3713-31-3; Glycoside Hydrolases, EC 3.2.1.-; Nitrobenzenes
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00086215_v323_n1-4_p7_Chiocconi

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Citas:

---------- APA ----------
Chiocconi, A., Marino, C. & De Lederkremer, R.M. (1999) . 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. Carbohydrate Research, 323(1-4), 7-13.
http://dx.doi.org/10.1016/S0008-6215(99)00241-4
---------- CHICAGO ----------
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" . Carbohydrate Research 323, no. 1-4 (1999) : 7-13.
http://dx.doi.org/10.1016/S0008-6215(99)00241-4
---------- MLA ----------
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" . Carbohydrate Research, vol. 323, no. 1-4, 1999, pp. 7-13.
http://dx.doi.org/10.1016/S0008-6215(99)00241-4
---------- VANCOUVER ----------
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. Carbohydr. Res. 1999;323(1-4):7-13.
http://dx.doi.org/10.1016/S0008-6215(99)00241-4