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Abstract:

D-Galactofuranose (D-Galf) is present in glycoconjugates of several pathogenic microorganisms but is absent in mammals, so it is a good target for the development of chemotherapeutic agents for the treatment of microbial infections. This fact has increased interest in the synthesis of D-Galf-containing molecules for corresponding glycobiological studies. The synthesis of oligosaccharides, glycoconjugates, and mimetics of D-Galf requires specific methods for the preparation of galactose derivatives in the furanosic configuration, the synthesis of appropriate acceptors, and efficient glycosylation methods for the construction of α- and β-D-Galf linkages. This review summarizes the different strategies developed for the preparation of partially protected derivatives of D-Galf, suitable as acceptors for the construction of (1→2), (1→3), (1→5), and (1→6) link- ages, and describes recent applications. Three rings to rule them all: For the synthesis of D-Galf oligosaccharides and glycoconjugates, partially protected derivatives of D-galactofuranose that are suitable as glycosyl acceptors are synthesized mainly from three types of derivatives (type I, II, and III). This review describes the diverse strategies developed for this purpose and recent applications. Copyright © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Registro:

Documento: Artículo
Título:Synthesis of D -galactofuranose-containing molecules: Design of galactofuranosyl acceptors
Autor:Marino, C.; Baldoni, L.
Filiación:CIHIDECAR-CONICET-UBA, Departamento de Química Orgánica, Ciudad Universitaria, Pabellõn II, 1428 Buenos Aires, Argentina
Palabras clave:carbohydrates; galactofuranosides; galactofuranosyl acceptors; glycosylation; organic synthesis; antiinfective agent; carbohydrate derivative; dextro galactofuranose derivative; galactofuranosyl acceptor; glycoconjugate; oligosaccharide; unclassified drug; carbohydrate; galactose; polysaccharide; carbohydrate synthesis; drug synthesis; glycobiology; glycosylation; linkage analysis; nonhuman; precursor; priority journal; review; chemistry; drug design; galactofuranosides; galactofuranosyl acceptors; methodology; organic synthesis; synthesis; Mammalia; carbohydrates; galactofuranosides; galactofuranosyl acceptors; glycosylation; organic synthesis; Chemistry Techniques, Synthetic; Drug Design; Galactose; Glycoconjugates; Glycosylation; Polysaccharides
Año:2014
Volumen:15
Número:2
Página de inicio:189
Página de fin:204
DOI: http://dx.doi.org/10.1002/cbic.201300638
Título revista:ChemBioChem
Título revista abreviado:ChemBioChem
ISSN:14394227
CODEN:CBCHF
CAS:galactose, 26566-61-0, 50855-33-9, 59-23-4
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_14394227_v15_n2_p189_Marino

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Citas:

---------- APA ----------
Marino, C. & Baldoni, L. (2014) . Synthesis of D -galactofuranose-containing molecules: Design of galactofuranosyl acceptors. ChemBioChem, 15(2), 189-204.
http://dx.doi.org/10.1002/cbic.201300638
---------- CHICAGO ----------
Marino, C., Baldoni, L. "Synthesis of D -galactofuranose-containing molecules: Design of galactofuranosyl acceptors" . ChemBioChem 15, no. 2 (2014) : 189-204.
http://dx.doi.org/10.1002/cbic.201300638
---------- MLA ----------
Marino, C., Baldoni, L. "Synthesis of D -galactofuranose-containing molecules: Design of galactofuranosyl acceptors" . ChemBioChem, vol. 15, no. 2, 2014, pp. 189-204.
http://dx.doi.org/10.1002/cbic.201300638
---------- VANCOUVER ----------
Marino, C., Baldoni, L. Synthesis of D -galactofuranose-containing molecules: Design of galactofuranosyl acceptors. ChemBioChem. 2014;15(2):189-204.
http://dx.doi.org/10.1002/cbic.201300638