Syntheses of ß-D-Galf-(1-6)-ß-D-Galf-(1-5)-D-Galf and ß-d-Galf-(1-->5)-ß-d-Galf-(1-->6)-d-Galf, trisaccharide units in the galactan of Mycobacterium tuberculosis

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

JOURNAL OF ORGANIC CHEMISTRY

American Chemical Society

Lugar: Washington, DC; Año: 2003 vol. 68 p. 6928 - 6934

0022-3263

The galactofuran is a crucial constituent of the cell wall of mycobacteria. An efficient synthesis of the two trisaccharide units of the galactan is described. The strategy relies on the use of substituted d-galactono-1,4-lactones as precursors for the internal and the reducing galactofuranoses. Dec-9-enyl beta-d-Galf-(1-->6)-beta-d-Galf-(1-->5)-beta-d-Galf (2) and dec-9-enyl beta-d-Galf-(1-->5)-beta-d-Galf-(1-->6)-beta-d-Galf (9) so far reported as convenient substrates for the galactofuranosyl transferase, and possibly useful for immunological studies, were obtained by the trichloroacetimidate method of glycosylation.