Synthesis of a tetrasaccharide fragment of mycobacterial arabinogalactan

LUCÍA, GANDOLFI-DONADÍO; CAROLA, GALLO-RODRÍGUEZ; ROSA, M. DE LEDERKREMER

CARBOHYDRATE RESEARCH

Elsevier

Lugar: New York; Año: 2008

0008-6215

Galactonolactone 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.