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Abstract:

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.

Registro:

Documento: Artículo
Título: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
Autor:Marino, C.; Chiocconi, A.; Varela, O.; De Lederkremer, R.M.
Filiación:CIHIDECAR, Depto. de Quim. Orgánica, Universidad de Buenos Aires, 1428 Buenos Aires, Argentina
Palabras clave: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
Año:1998
Volumen:311
Número:4
Página de inicio:183
Página de fin:189
DOI: http://dx.doi.org/10.1016/S0008-6215(98)00214-6
Título revista:Carbohydrate Research
Título revista abreviado:Carbohydr. Res.
ISSN:00086215
CODEN:CRBRA
CAS:3-deoxy-xylo-hexofuranosyl-(1-3)-Manp; beta-Galactosidase, EC 3.2.1.23; Disaccharides; exo-beta-D-galactofuranosidase, EC 3.2.1.-; Glycoside Hydrolases, EC 3.2.1.-; Glycosphingolipids; lipophosphonoglycan
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00086215_v311_n4_p183_Marino

Referencias:

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Citas:

---------- APA ----------
Marino, C., Chiocconi, A., Varela, O. & De Lederkremer, R.M. (1998) . 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. Carbohydrate Research, 311(4), 183-189.
http://dx.doi.org/10.1016/S0008-6215(98)00214-6
---------- CHICAGO ----------
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" . Carbohydrate Research 311, no. 4 (1998) : 183-189.
http://dx.doi.org/10.1016/S0008-6215(98)00214-6
---------- MLA ----------
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" . Carbohydrate Research, vol. 311, no. 4, 1998, pp. 183-189.
http://dx.doi.org/10.1016/S0008-6215(98)00214-6
---------- VANCOUVER ----------
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. Carbohydr. Res. 1998;311(4):183-189.
http://dx.doi.org/10.1016/S0008-6215(98)00214-6