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Abstract:

With the aim of developing synthetic tools for the characterization of galactofuranosyltransferases, the synthesis of 9-decenyl glycosides of d-Manp, d-Galf, and β-d-Galf-(1→3)-d-Manp was targeted. The interest in the alkenyl aglycone arises via potential conjugation reactions, once the terminal double bond has been conveniently functionalized. The glycosylation of β-d-Galf-(1→3)-d-Manp was attempted by two different approaches: the trichloroacetimidate method and the glycosylation via the glycosyl iodide. The conditions for the latter were established on the basis of glycosylation assays of per-O-acetylmannose. On the other hand, the study of glycosylation reactions via per-O-benzoylated galactofuranosyl iodide confirms the versatility of glycosyl iodides as donors.

Registro:

Documento: Artículo
Título:Synthetic tools for the characterization of galactofuranosyl transferases: Glycosylations via acylated glycosyl iodides
Autor:Baldoni, L.; Marino, C.
Filiación:CIHIDECAR-CONICET, Departamento de Química Orgánica, Universidad de Buenos Aires, Buenos Aires 1428, Argentina
Palabras clave:Galactofuranosyl transferases; Mannopyranosyl iodide; per-O-Benzoylated-galactofuranosyl iodide; per-O-tert-Butyldimethylsilyl-β-d-galactofuranose; Functionalized; Galactofuranosyl transferases; Glycosylation assay; Glycosylation reactions; Mannopyranosyl iodide; per-O-Benzoylated-galactofuranosyl iodide; Terminal double bonds; Trichloroacetimidate; Enzymes; Esterification; Glycosylation; galactofuranosyl transferase; glycosyl iodide; iodide; pyranoside; transferase; trichloroacetimidic acid; unclassified drug; acylation; article; enzyme assay; glycosylation; priority journal; proton nuclear magnetic resonance; reaction analysis; Acylation; Carbohydrate Conformation; Galactosyltransferases; Glycosides; Glycosylation; Iodides
Año:2013
Volumen:374
Página de inicio:75
Página de fin:81
DOI: http://dx.doi.org/10.1016/j.carres.2013.03.032
Título revista:Carbohydrate Research
Título revista abreviado:Carbohydr. Res.
ISSN:00086215
CODEN:CRBRA
CAS:iodide, 20461-54-5; transferase, 9047-61-4; Galactosyltransferases, 2.4.1.-; Glycosides; Iodides
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00086215_v374_n_p75_Baldoni

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Citas:

---------- APA ----------
Baldoni, L. & Marino, C. (2013) . Synthetic tools for the characterization of galactofuranosyl transferases: Glycosylations via acylated glycosyl iodides. Carbohydrate Research, 374, 75-81.
http://dx.doi.org/10.1016/j.carres.2013.03.032
---------- CHICAGO ----------
Baldoni, L., Marino, C. "Synthetic tools for the characterization of galactofuranosyl transferases: Glycosylations via acylated glycosyl iodides" . Carbohydrate Research 374 (2013) : 75-81.
http://dx.doi.org/10.1016/j.carres.2013.03.032
---------- MLA ----------
Baldoni, L., Marino, C. "Synthetic tools for the characterization of galactofuranosyl transferases: Glycosylations via acylated glycosyl iodides" . Carbohydrate Research, vol. 374, 2013, pp. 75-81.
http://dx.doi.org/10.1016/j.carres.2013.03.032
---------- VANCOUVER ----------
Baldoni, L., Marino, C. Synthetic tools for the characterization of galactofuranosyl transferases: Glycosylations via acylated glycosyl iodides. Carbohydr. Res. 2013;374:75-81.
http://dx.doi.org/10.1016/j.carres.2013.03.032