title: Synthesis of a tetrasaccharide fragment of mycobacterial arabinogalactan.
abstract: The arabinogalactan of mycobacteria contains both monosaccharides in the furanose ring form, which are absent in mammals. We report here the first synthesis of the tetrasaccharide fragment alpha-D-Araf-(1-->5)-beta-D-Galf-(1-->5)-beta-D-Galf-(1-->6)-D-Galf, conveniently derivatized for further elongation. The strategy relied on the use of suitably substituted D-galactono-1,4-lactones as precursors for the galactofuranose units. Reduction of lactone tetrasaccharide 9 with disiamylborane afforded the tetrasaccharide synthon 1. The tetrasaccharide contains the linker unit of the arabinan to the galactan.
authors.affiliation: CIHIDECAR, Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Ciudad Universitaria, Pabellón II, Buenos Aires, Argentina.
authors.forename: Lucía
authors.initials: L
authors.lastname: Gandolfi-Donadío
authors.forename: Carola
authors.initials: C
authors.lastname: Gallo-Rodriguez
authors.forename: Rosa M
authors.initials: RM
authors.lastname: de Lederkremer
mesh_terms: D002240:Carbohydrate Sequence; D005685:Galactans / Q000138:chemical synthesis*; D009169:Mycobacterium tuberculosis / Q000737:chemistry; D009844:Oligosaccharides / Q000138:chemical synthesis*
chemical_list: D005685:Galactans; D009844:Oligosaccharides; C005653:arabinogalactan