Synthesis of a tetrasaccharide fragment of mycobacterial arabinogalactan.

GANDOLFI-DONADIO, L; GALLO-RODRIGUEZ, C; MUCHNIK DE LEDERKREMER, R

CARBOHYDRATE RESEARCH

Elsevier

Lugar: Amsterdam; Año: 2007

0008-6215

The arabinogalactan of mycobacteria contains both monosaccharides in the furanose ring form, absent in mammals. We report here the first synthesis of the tetrasaccharide fragment á-D-Araf-(1-5)-â-D-Galf-(1-5)-â-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 with disiamylborane of the lactone tetrasaccharide 9 afforded the tetrasaccharide synthon 1. The tetrasaccharide contains the linker unit of the arabinan to the galactan.