Synthesis of α- d-Gal f-(1→2)- d-galactitol and α- d-Gal f-(1→2)[β- d-Gal f-(1→3)]- d-galactitol, oligosaccharide derivatives from Bacteroides cellulosolvens glycoproteins

The synthesis of α- d-galactofuranosyl-(1→2)- d-galactitol, which has been isolated by reductive β-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 met...

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Bibliographic Details
Published in:Carbohydrate research 2006-11, Vol.341 (15), p.2487-2497
Main Authors: Gandolfi-Donadío, Lucía, Gola, Gabriel, de Lederkremer, Rosa M., Gallo-Rodriguez, Carola
Format: Article
Language:English
Subjects:
1,2-cis-Glycosylation
Aldonolactone
Bacteroides - chemistry
Bacteroides cellulosolvens
Carbohydrate Sequence
Clostridium thermocellum
Galactitol
Galactose
Glycoproteins - chemistry
Indicators and Reagents
Models, Molecular
Molecular Sequence Data
Trichloroacetimidate
Trisaccharides - chemical synthesis
Trisaccharides - chemistry
α- d-Galactofuranosyl
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Summary:The synthesis of α- d-galactofuranosyl-(1→2)- d-galactitol, which has been isolated by reductive β-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 α- d-Gal f-(1→2)[β- 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 α- d-Gal f, previously found in natural products.
ISSN:0008-6215
1873-426X
DOI:10.1016/j.carres.2006.07.013