Syntheses of beta-d-Galf-(1-->6)-beta-d-Galf-(1-->5)-d-Galf and beta-d-Galf-(1-->5)-beta-d-Galf-(1-->6)-d-Galf, trisaccharide units in the galactan of Mycobacterium tuberculosis.
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.
Gandolfi-Donadío
Lucía
L
CIHIDECAR, Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Ciudad Universitaria, Pabellón II, 1428 Buenos Aires, Argentina.
Gallo-Rodriguez
Carola
C
de Lederkremer
Rosa M
RM
D002240:Carbohydrate Sequence; D002855:Chromatography, Thin Layer; D005663:Furans / Q000138:chemical synthesis*; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D008969:Molecular Sequence Data; D009169:Mycobacterium tuberculosis / Q000737:chemistry*; D013237:Stereoisomerism; D014312:Trisaccharides / Q000138:chemical synthesis*; D014315:Triterpenes / Q000138:chemical synthesis*
D005663:Furans; D007202:Indicators and Reagents; D014312:Trisaccharides; D014315:Triterpenes; C481821:dumsin