BIOMAT Database Logo BIOMAT Database Logo

Synthesis of regioisomeric methyl alpha-L-arabinofuranobiosides. 1995

Y Kawabata, and S Kaneko, and I Kusakabe, and Y Gama
Institute of Applied Biochemistry, University of Tsukuba, Ibaraki, Japan.

The three regioisomers of methyl alpha-L-arabinofuranobioside, namely methyl O-alpha-L-arabinofuranosyl-(1-->2)-alpha-L-arabinofuranoside, methyl O-alpha-L-arabinofuranosyl-(1-->3)-alpha-L-arabinofuranoside, and methyl O-alpha-L-arabinofuranosyl-(1-->5)-alpha-L-arabinofuranoside, were synthesized for use as substrates in studies of the specificity of alpha-L-arabinofuranosidase. The regiospecifically protected precursors, namely methyl 3,5-di-O-benzoyl-alpha-L-arabinofuranoside, methyl 2,5-di-O-benzyl-alpha-L-arabinofuranoside, and methyl 2,3-di-O-benzoyl-alpha-L-arabinofuranoside, were prepared from 2,3,5-tri-O-benzoyl-alpha-L-arabinofuranosyl chloride (4) and methyl 5-O-trityl-alpha-L-arabinofuranoside, respectively, and glycosylated with 4 in the presence of silver trifluoromethanesulfonate and s-collidine. 1H and 13C NMR data for all compounds are presented.

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
D002855 Chromatography, Thin Layer Chromatography on thin layers of adsorbents rather than in columns. The adsorbent can be alumina, silica gel, silicates, charcoals, or cellulose. (McGraw-Hill Dictionary of Scientific and Technical Terms, 4th ed) Chromatography, Thin-Layer,Thin Layer Chromatography,Chromatographies, Thin Layer,Chromatographies, Thin-Layer,Thin Layer Chromatographies,Thin-Layer Chromatographies,Thin-Layer Chromatography
D004187 Disaccharides Oligosaccharides containing two monosaccharide units linked by a glycosidic bond. Disaccharide
D006026 Glycoside Hydrolases Any member of the class of enzymes that catalyze the cleavage of the glycosidic linkage of glycosides and the addition of water to the resulting molecules. Endoglycosidase,Exoglycosidase,Glycohydrolase,Glycosidase,Glycosidases,Glycoside Hydrolase,Endoglycosidases,Exoglycosidases,Glycohydrolases,Hydrolase, Glycoside,Hydrolases, Glycoside
D001089 Arabinose L-Arabinose,L Arabinose
D013237 Stereoisomerism The phenomenon whereby compounds whose molecules have the same number and kind of atoms and the same atomic arrangement, but differ in their spatial relationships. (From McGraw-Hill Dictionary of Scientific and Technical Terms, 5th ed) Molecular Stereochemistry,Stereoisomers,Stereochemistry, Molecular,Stereoisomer

Related Publications

Y Kawabata, and S Kaneko, and I Kusakabe, and Y Gama
Synthesis of methyl alpha-L-vancosaminide.
January 2000, Carbohydrate research,
Y Kawabata, and S Kaneko, and I Kusakabe, and Y Gama
Synthesis of L-alpha-phosphatidyl-(alpha-methyl)cholines.
February 1967, Canadian journal of biochemistry,
Y Kawabata, and S Kaneko, and I Kusakabe, and Y Gama
Facile synthesis of methyl 2-O-alpha-L-rhamnopyranosyl-alpha-L-rhamnopyranoside and methyl 2-O-alpha-L-mannopyranosyl-alpha-L-rhamnopyranoside.
September 1992, Bioscience, biotechnology, and biochemistry,
Y Kawabata, and S Kaneko, and I Kusakabe, and Y Gama
Stereoselective total synthesis of methyl alpha-D and alpha-L-glucopyranosides.
May 1977, Carbohydrate research,
Y Kawabata, and S Kaneko, and I Kusakabe, and Y Gama
Synthesis of enantiomerically pure alpha-[14C]methyl-L-tryptophan.
September 1993, Applied radiation and isotopes : including data, instrumentation and methods for use in agriculture, industry and medicine,
Y Kawabata, and S Kaneko, and I Kusakabe, and Y Gama
A novel synthesis of methyl 2-O-methyl-alpha,beta-L-fucofuranoside.
September 1990, Carbohydrate research,
Y Kawabata, and S Kaneko, and I Kusakabe, and Y Gama
Synthesis of 4-O-alpha-L-fucopyranosyl-L-fucose and methyl 4-O-beta-L-fucopyranosyl-alpha-L-fucopyranoside.
May 1975, Carbohydrate research,
Y Kawabata, and S Kaneko, and I Kusakabe, and Y Gama
Synthesis of "no-carrier-added" alpha-[11C]methyl-L-tryptophan.
March 1988, Journal of nuclear medicine : official publication, Society of Nuclear Medicine,
Y Kawabata, and S Kaneko, and I Kusakabe, and Y Gama
Stereospecific synthesis of alpha-methyl-L-glutamine by glutamine synthetase.
June 1965, Biochemistry,
Y Kawabata, and S Kaneko, and I Kusakabe, and Y Gama
Synthesis of methyl 2,4-di-O-methyl-3-O-(2-O-methyl-alpha-L-rhamnopyranosyl)-alpha-L- rhamnopyranoside and methyl 2,4-di-O-methyl-3-O-[2-O-methyl-3-O-(2-O-methyl-alpha-L-fucopyranosyl)- alpha-L-rhamnopyranosyl]-alpha-L-rhamnopyranoside: di- and tri-saccharide segments of a phenolic glycolipid of Mycobacterium kansasii.
March 1992, Carbohydrate research,
Copied contents to your clipboard!