Synthesis of alpha-D-Gal f-(1-->2)-D-galactitol and alpha-D-Gal f-(1-->2)[beta-D-Gal f-(1-->3)]-D-galactitol, oligosaccharide derivatives from Bacteroides cellulosolvens glycoproteins.
The synthesis of alpha-D-galactofuranosyl-(1-->2)-D-galactitol, which has been isolated by reductive beta-elimination from glycoproteins of Bacteroides cellulosolvens and Clostridium thermocellum, is described. The approach of selective glycosylation of an aldono-1,4-lactone by the trichloroacetimidate method was employed. The synthesis of alpha-D-Gal f-(1-->2)[beta-D-Gal f-(1-->3)]-D-Galol, that contains Gal f units in both anomeric configurations, is also reported. These are the first synthetic oligosaccharides with alpha-D-Gal f, previously found in natural products.
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.
Gola
Gabriel
G
de Lederkremer
Rosa M
RM
Gallo-Rodriguez
Carola
C
D001439:Bacteroides / Q000737:chemistry*; D002240:Carbohydrate Sequence; D004376:Galactitol; D005690:Galactose; D006023:Glycoproteins / Q000737:chemistry*; D007202:Indicators and Reagents; D008958:Models, Molecular; D008969:Molecular Sequence Data; D014312:Trisaccharides / Q000138:chemical synthesis* / Q000737:chemistry
D006023:Glycoproteins; D007202:Indicators and Reagents; D014312:Trisaccharides; D004376:Galactitol; D005690:Galactose