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Abstract:

Derivatives of 5-deoxy-β-d-galactofuranose (5-deoxy-α-l-arabino- hexofuranose) have been synthesized starting from d-galacturonic acid. The synthesis of methyl 5-deoxy-α-l-arabino-hexofuranoside (14α) was achieved by an efficient strategy previously optimized, involving a photoinduced electron transfer (PET) deoxygenation. Compound 14α was converted into per-O-acetyl-5-deoxy-α,β-l-arabino-hexofuranoside (16), an activated precursor for glycosylation reactions. The SnCl 4-promoted glycosylation of 16 led to 4-nitrophenyl (19α), and 4-methylthiophenyl 5-deoxy-α-l-arabino-hexofuranosides (20α). The oxygenated analog 4-methylphenyl 1-thio-β-d-galactofuranoside (23β) was also prepared. The 5-deoxy galactofuranosides were evaluated as inhibitors or substrates of the exo-β-d-galactofuranosidase from Penicillium fellutanum, showing that the absence of HO-5 drastically diminishes the affinity for the protein. © 2010 Elsevier Ltd. All rights reserved.

Registro:

Documento: Artículo
Título:Synthesis of 5-deoxy-β-d-galactofuranosides as tools for the characterization of β-d-galactofuranosidases
Autor:Bordoni, A.; De Lederkremer, R.M.; Marino, C.
Filiación:CIHIDECAR-CONICET, Departamento de Química Orgánica, Ciudad Universitaria, 1428 Buenos Aires, Argentina
Palabras clave:5-Deoxy-d-galactofuranosides; Galactofuranosidase inhibition; Galactofuranosidase substrates; PET deoxygenation; 4 methylphenyl 1 thio beta dextro galactofuranoside; 4 methylthiophenyl 5 deoxy alpha levo arabinohexofuranoside; 4 nitrophenyl 5 deoxy alpha levo arabinohexofuranoside; 5 deoxy alpha levo arabinohexofuranoside; 5 deoxy beta dextro galactofuranose; galacturonic acid; per o acetyl 5 deoxy alpha,beta levo arabinohexofuranoside; unclassified drug; article; electron transport; enzyme activity; enzyme synthesis; protein binding; Galactosides; Glycoside Hydrolases; Penicillium; Substrate Specificity; Penicillium fellutanum
Año:2010
Volumen:18
Número:14
Página de inicio:5339
Página de fin:5345
DOI: http://dx.doi.org/10.1016/j.bmc.2010.05.038
Título revista:Bioorganic and Medicinal Chemistry
Título revista abreviado:Bioorg. Med. Chem.
ISSN:09680896
CODEN:BMECE
CAS:galacturonic acid, 14982-50-4, 685-73-4; Galactosides; Glycoside Hydrolases, 3.2.1.-; exo-beta-D-galactofuranosidase, 3.2.1.146
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_09680896_v18_n14_p5339_Bordoni

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Citas:

---------- APA ----------
Bordoni, A., De Lederkremer, R.M. & Marino, C. (2010) . Synthesis of 5-deoxy-β-d-galactofuranosides as tools for the characterization of β-d-galactofuranosidases. Bioorganic and Medicinal Chemistry, 18(14), 5339-5345.
http://dx.doi.org/10.1016/j.bmc.2010.05.038
---------- CHICAGO ----------
Bordoni, A., De Lederkremer, R.M., Marino, C. "Synthesis of 5-deoxy-β-d-galactofuranosides as tools for the characterization of β-d-galactofuranosidases" . Bioorganic and Medicinal Chemistry 18, no. 14 (2010) : 5339-5345.
http://dx.doi.org/10.1016/j.bmc.2010.05.038
---------- MLA ----------
Bordoni, A., De Lederkremer, R.M., Marino, C. "Synthesis of 5-deoxy-β-d-galactofuranosides as tools for the characterization of β-d-galactofuranosidases" . Bioorganic and Medicinal Chemistry, vol. 18, no. 14, 2010, pp. 5339-5345.
http://dx.doi.org/10.1016/j.bmc.2010.05.038
---------- VANCOUVER ----------
Bordoni, A., De Lederkremer, R.M., Marino, C. Synthesis of 5-deoxy-β-d-galactofuranosides as tools for the characterization of β-d-galactofuranosidases. Bioorg. Med. Chem. 2010;18(14):5339-5345.
http://dx.doi.org/10.1016/j.bmc.2010.05.038