BIOMAT Database Logo BIOMAT Database Logo

Synthesis of methyl 3-O-(alpha-D-glucopyranosyl)-7-O-(L-glycero-alpha-D- manno-heptopyranosyl)-L-glycero-alpha-D-manno-heptopyranoside. 1990

P J Garegg, and S Oscarson, and M Szönyi
Department of Organic Chemistry, Arrhenius Laboratory, University of Stockholm, Sweden.

The title trisaccharide glycoside, which is related to part of the core region of the lipopolysaccharide from Salmonella, and the disaccharide glycosides methyl 3-O-alpha-D-glucopyranosyl-L-glycero-alpha-D-manno-heptopyranoside and methyl 7-O-L-glycero-alpha-D-manno-heptopyranosyl-L-glycero-alpha-D-manno- heptopyranoside have been synthesised. Methyl 2,3,4-tri-O-benzyl-L-glycero-alpha-D-manno- heptopyranoside, obtained via a one-carbon elongation at C-6 of methyl 2,3,4-tri-O-benzyl-alpha-D-manno- hexodialdo-1,5-pyranoside, was used as precursor both for the heptosyl donor and acceptor.

UI MeSH Term Description Entries
D008070 Lipopolysaccharides Lipid-containing polysaccharides which are endotoxins and important group-specific antigens. They are often derived from the cell wall of gram-negative bacteria and induce immunoglobulin secretion. The lipopolysaccharide molecule consists of three parts: LIPID A, core polysaccharide, and O-specific chains (O ANTIGENS). When derived from Escherichia coli, lipopolysaccharides serve as polyclonal B-cell mitogens commonly used in laboratory immunology. (From Dorland, 28th ed) Lipopolysaccharide,Lipoglycans
D008759 Methylglycosides
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
D012475 Salmonella A genus of gram-negative, facultatively anaerobic, rod-shaped bacteria that utilizes citrate as a sole carbon source. It is pathogenic for humans, causing enteric fevers, gastroenteritis, and bacteremia. Food poisoning is the most common clinical manifestation. Organisms within this genus are separated on the basis of antigenic characteristics, sugar fermentation patterns, and bacteriophage susceptibility.
D014312 Trisaccharides Oligosaccharides containing three monosaccharide units linked by glycosidic bonds. Trisaccharide
D015394 Molecular Structure The location of the atoms, groups or ions relative to one another in a molecule, as well as the number, type and location of covalent bonds. Structure, Molecular,Molecular Structures,Structures, Molecular

Related Publications

P J Garegg, and S Oscarson, and M Szönyi
Synthesis of 3-O- and 4-O-(2-aminoethylphosphono) derivatives of methyl l-glycero-α-d-manno-heptopyranoside.
January 2017, Monatshefte fur chemie,
P J Garegg, and S Oscarson, and M Szönyi
The synthesis and characterisation of 6-O-L-glycero-alpha-D-manno-heptopyranosyl-D-glucopyranose.
August 1991, Carbohydrate research,
P J Garegg, and S Oscarson, and M Szönyi
Synthesis of Pseudomonas aeruginosa lipopolysaccharide core antigens containing 7-O-carbamoyl-L-glycero-alpha-D-manno-heptopyranosyl residues.
April 1999, Carbohydrate research,
P J Garegg, and S Oscarson, and M Szönyi
Crystal and molecular structure of methyl L-glycero-α-D-manno-heptopyranoside, and synthesis of 1→7 linked L-glycero-D-manno-heptobiose and its methyl α-glycoside.
September 2011, Carbohydrate research,
P J Garegg, and S Oscarson, and M Szönyi
Isolation and structural analysis of the tetrasaccharide 3-deoxy-5-O-[3-O- (3-O-alpha-D-glucopyranosyl-L-glycero-alpha-D-manno-heptopyranosyl)-L-g lycero- alpha-D-manno-heptopyranosyl]-D-manno-octulosonic acid from the core region of the lipopolysaccharide of Salmonella minnesota strain R5 (rough mutant chemotype RcP-).
July 1993, Carbohydrate research,
P J Garegg, and S Oscarson, and M Szönyi
The synthesis and characterisation of 2-O-(6-O-L-glycero-alpha,beta-D-manno-heptopyranosyl-alpha-D-glucopyran osyl)-alpha,beta-D-glucopyranose.
July 1992, Carbohydrate research,
P J Garegg, and S Oscarson, and M Szönyi
Stereocontrolled synthesis of the D- and L-glycero-beta-D-manno-heptopyranosides and their 6-deoxy analogues. Synthesis of methyl alpha-l-rhamno-pyranosyl-(1-->3)-D-glycero-beta-D-manno-heptopyranosyl- (1-->3)-6-deoxy-glycero-beta-D-manno-heptopyranosyl-(1-->4)-alpha-L- rhamno-pyranoside, a tetrasaccharide subunit of the lipopolysaccharide from Plesimonas shigelloides.
June 2006, Journal of the American Chemical Society,
P J Garegg, and S Oscarson, and M Szönyi
Synthesis of linear oligosaccharides: L-glycero-alpha-D-manno-heptopyranosyl derivatives of allyl alpha-glycosides of D-glucose, kojibiose, and 3-O-alpha-kojibiosyl-D-glucose, substrates for synthetic antigens.
February 1994, Carbohydrate research,
P J Garegg, and S Oscarson, and M Szönyi
7-O-(2-Amino-2-deoxy-alpha-D-glucopyranosyl)-L-glycero-D-manno-heptose. A constituent of the endotoxin of Bordetella pertussis.
November 1976, European journal of biochemistry,
P J Garegg, and S Oscarson, and M Szönyi
2-O-(beta-D-glucuronyl)-7-O-(2-amino-2-deoxy-alpha-D-glucopyranosyl)-L-glycero-D-manno-heptose: a constituent of the Bordetella pertussis endotoxin.
June 1977, European journal of biochemistry,
Copied contents to your clipboard!