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Synthesis of the Forssman pentasaccharide and terminal tetra-, tri-, and di-saccharide fragments. 1994

U Nilsson, and A K Ray, and G Magnusson
Chemical Center, Lund Institute of Technology, University of Lund, Sweden.

The 2-(trimethylsilyl)ethyl (TMSEt) beta-glycosides of the Forssman pentasaccharide [alpha-D-GalNAc-(1-->3)-beta-D-GalNAc-(1-->3)-alpha-D-Gal- (1-->4)-beta-D-Gal-(1-->4)-D-Glc] and the terminal tetrasaccharide, as well as the methyl glycosides 1 and 2 of the terminal di- and tri-saccharides, were synthesised by silver trifluoromethanesulfonate-promoted alpha-glycosylation of suitably protected mono-, di-, tri-, and tetrasaccharide alcohols with 3,4,6-tri-O-acetyl-2-azido-2-deoxy-alpha-D-galactopyranosyl bromide, followed by removal of protecting groups. The anomeric TMSEt group of the Forssman pentasaccharide and terminal tetrasaccharide was removed with trifluoroacetic acid-dichloromethane, to give the corresponding hemiacetal sugars 4 and 6.

UI MeSH Term Description Entries
D008969 Molecular Sequence Data Descriptions of specific amino acid, carbohydrate, or nucleotide sequences which have appeared in the published literature and/or are deposited in and maintained by databanks such as GENBANK, European Molecular Biology Laboratory (EMBL), National Biomedical Research Foundation (NBRF), or other sequence repositories. Sequence Data, Molecular,Molecular Sequencing Data,Data, Molecular Sequence,Data, Molecular Sequencing,Sequencing Data, Molecular
D009844 Oligosaccharides Carbohydrates consisting of between two (DISACCHARIDES) and ten MONOSACCHARIDES connected by either an alpha- or beta-glycosidic link. They are found throughout nature in both the free and bound form. Oligosaccharide
D002240 Carbohydrate Sequence The sequence of carbohydrates within POLYSACCHARIDES; GLYCOPROTEINS; and GLYCOLIPIDS. Carbohydrate Sequences,Sequence, Carbohydrate,Sequences, Carbohydrate
D004187 Disaccharides Oligosaccharides containing two monosaccharide units linked by a glycosidic bond. Disaccharide
D005577 Forssman Antigen A glycolipid, cross-species antigen that induces production of antisheep hemolysin. It is present on the tissue cells of many species but absent in humans. It is found in many infectious agents. Antigen, Forssman
D005915 Globosides Glycosphingolipids containing N-acetylglucosamine (paragloboside) or N-acetylgalactosamine (globoside). Globoside is the P antigen on erythrocytes and paragloboside is an intermediate in the biosynthesis of erythrocyte blood group ABH and P 1 glycosphingolipid antigens. The accumulation of globoside in tissue, due to a defect in hexosaminidases A and B, is the cause of Sandhoff disease. Cytolipins,Lacto-N-neotetraosylceramide,Lacto-N-tetraosylceramide,Lactoneotetraosylceramide,Lacto N neotetraosylceramide,Lacto N tetraosylceramide
D014312 Trisaccharides Oligosaccharides containing three monosaccharide units linked by glycosidic bonds. Trisaccharide

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