Biomaterial Database

Synthesis of a tetrasaccharide donor corresponding to the O-specific polysaccharide of Shigella dysenteriae type 1. 1993

V Pozsgay, and C P Glaudemans, and J B Robbins, and R Schneerson

Laboratory of Developmental and Molecular Immunity, National Institute of Child Health and Human Development, Bethesda, MD 20892.

O-(2,4-Di-O-benzoyl-3-O-chloroacetyl-alpha-L-rhamnopyranosyl)-(1--> 2)-O-(3,4,6-tri-O-benzoyl-alpha-D-galactopyranosyl)-(1--> 3)-O-(2-acetamido-4,6-di-O-acetyl-2-deoxy-alpha-D-glucopyranosyl)-(1--> 3)-2,4-di-O-benzoyl-alpha-L-rhamnopyranosyl trichloroacetimidate (1) was synthesized in a stepwise manner, using the following monosaccharide units: 2-(trimethylsilyl)ethyl 2,4-di-O-benzoyl-alpha-L-rhamnopyranoside, 2-azido-4,6-O-benzylidene-3-O-chloroacetyl-2-deoxy-beta-D-glucopyranosyl chloride, methyl 3,4,6-tri-O-benzoyl-2-O -(4-methoxybenzyl)-1-thio-beta-D-galactopyranoside, and 2,4-di-O-benzoyl-3-O-chloroacetyl-alpha-L-rhamnopyranosyl chloride. Compound 1 corresponds to a complete tetrasaccharide repeating unit of the O-specific polysaccharide of the lipopolysaccharide of Shigella dysenteriae type 1.

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
D011135	Polysaccharides, Bacterial	Polysaccharides found in bacteria and in capsules thereof.	Bacterial Polysaccharides
D002240	Carbohydrate Sequence	The sequence of carbohydrates within POLYSACCHARIDES; GLYCOPROTEINS; and GLYCOLIPIDS.	Carbohydrate Sequences,Sequence, Carbohydrate,Sequences, Carbohydrate
D006031	Glycosylation	The synthetic chemistry reaction or enzymatic reaction of adding carbohydrate or glycosyl groups. GLYCOSYLTRANSFERASES carry out the enzymatic glycosylation reactions. The spontaneous, non-enzymatic attachment of reducing sugars to free amino groups in proteins, lipids, or nucleic acids is called GLYCATION (see MAILLARD REACTION).	Protein Glycosylation,Glycosylation, Protein
D012762	Shigella dysenteriae	A species of gram-negative, facultatively anaerobic, rod-shaped bacteria that is extremely pathogenic and causes severe dysentery. Infection with this organism often leads to ulceration of the intestinal epithelium.	Bacillus dysenteriae,Bacillus dysentericus,Bacillus shigae,Eberthella dysenteriae,Shigella shigae