Biomaterial Database

Synthesis of specifically deoxygenated disaccharide derivatives of the Shigella dysenteriae type 1 O-antigen. 1995

L A Mulard, and C P Claudemans

NIDDK, National Institutes of Health, Bethesda, Maryland 20892, USA.

The synthesis of methyl O-alpha-L-rhamnopyranosyl-(1-->2)-alpha-D-galactopyranosides specifically deoxygenated at position 2 (31), or 4 (21) of the rhamnopyranosyl residue was accomplished using methyl 3,4,6-tri-O-benzoyl-alpha-D-galactopyranoside (18) as the glycosyl acceptor. Phenyl thionocarbonate activation of the penta-O-benzoylated disaccharide precursor followed by Barton reduction and Zemplén transesterification gave 31, while 21 was obtained via condensation of the deoxygenated monosaccharide donor with 18, and subsequent debenzoylation of the product.

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
D009682	Magnetic Resonance Spectroscopy	Spectroscopic method of measuring the magnetic moment of elementary particles such as atomic nuclei, protons or electrons. It is employed in clinical applications such as NMR Tomography (MAGNETIC RESONANCE IMAGING).	In Vivo NMR Spectroscopy,MR Spectroscopy,Magnetic Resonance,NMR Spectroscopy,NMR Spectroscopy, In Vivo,Nuclear Magnetic Resonance,Spectroscopy, Magnetic Resonance,Spectroscopy, NMR,Spectroscopy, Nuclear Magnetic Resonance,Magnetic Resonance Spectroscopies,Magnetic Resonance, Nuclear,NMR Spectroscopies,Resonance Spectroscopy, Magnetic,Resonance, Magnetic,Resonance, Nuclear Magnetic,Spectroscopies, NMR,Spectroscopy, MR
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
D005697	Galactosides	Glycosides formed by the reaction of the hydroxyl group on the anomeric carbon atom of galactose with an alcohol to form an acetal. They include both alpha- and beta-galactosides.
D012210	Rhamnose	A methylpentose whose L- isomer is found naturally in many plant glycosides and some gram-negative bacterial lipopolysaccharides.	Deoxymannose,Rhamnose, L-Isomer,Rhamnose, L Isomer
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
D019081	O Antigens	The lipopolysaccharide-protein somatic antigens, usually from gram-negative bacteria, important in the serological classification of enteric bacilli. The O-specific chains determine the specificity of the O antigens of a given serotype. O antigens are the immunodominant part of the lipopolysaccharide molecule in the intact bacterial cell. (From Singleton & Sainsbury, Dictionary of Microbiology and Molecular Biology, 2d ed)	O-Antigen,O-Specific Polysaccharides,O Antigen,O Antigen, Bacterial,O-Antigens,O-Specific Polysaccharide,Antigen, Bacterial O,Antigen, O,Antigens, O,Bacterial O Antigen,O Specific Polysaccharide,O Specific Polysaccharides,Polysaccharide, O-Specific,Polysaccharides, O-Specific