BIOMAT Database Logo BIOMAT Database Logo

Analysis of oligosaccharides containing 2-deoxy-alpha-D-arabino-hexosyl residues by the reductive-cleavage method. 1994

P Mischnick, and B Evers, and J Thiem
University of Hamburg, Institute of Organic Chemistry, Germany.

A mixture of oligosaccharides containing (1-->4)-linked 2-deoxy-alpha-D-arabino-hexosyl ("2-deoxyglucosyl") and (1-->4)-linked alpha-D-glucosyl residues (1) was analyzed by reduction, permethylation (perethylation), degradation to monomers, and GLC-MS. Degradation was performed either by hydrolysis with subsequent reduction, by methanolysis, or by reductive cleavage, always followed by acetylation. Reductive cleavage turned out to be the method of choice for the acid-labile 2-deoxy sugars. The main degradation product formed during acid hydrolysis of 2-deoxy-D-arabino-hexosyl residues yielded, after reduction and acetylation, (4R,S)-6-O-acetyl-2,3,5-trideoxyhexono-1,4-lactone (7). By methanolysis, in addition to the expected methyl glycosides, methyl 2,3,5-trideoxy-6-O-methyl-4-hexulosonate (12) is formed as a by-product. For determination of the distribution of chain lengths, the permethylated oligomers were separated by reversed-phase HPLC. For peak assignment, one isolated oligomer was investigated by FABMS and 1H NMR spectroscopy. The average degree of polymerization (dp) calculated from the HPLC chromatogram is in good agreement with the reductive-cleavage results.

UI MeSH Term Description Entries
D007202 Indicators and Reagents Substances used for the detection, identification, analysis, etc. of chemical, biological, or pathologic processes or conditions. Indicators are substances that change in physical appearance, e.g., color, at or approaching the endpoint of a chemical titration, e.g., on the passage between acidity and alkalinity. Reagents are substances used for the detection or determination of another substance by chemical or microscopical means, especially analysis. Types of reagents are precipitants, solvents, oxidizers, reducers, fluxes, and colorimetric reagents. (From Grant & Hackh's Chemical Dictionary, 5th ed, p301, p499) Indicator,Reagent,Reagents,Indicators,Reagents and Indicators
D007700 Kinetics The rate dynamics in chemical or physical systems.
D008320 Maltose A dextrodisaccharide from malt and starch. It is used as a sweetening agent and fermentable intermediate in brewing. (Grant & Hackh's Chemical Dictionary, 5th ed)
D008401 Gas Chromatography-Mass Spectrometry A microanalytical technique combining mass spectrometry and gas chromatography for the qualitative as well as quantitative determinations of compounds. Chromatography, Gas-Liquid-Mass Spectrometry,Chromatography, Gas-Mass Spectrometry,GCMS,Spectrometry, Mass-Gas Chromatography,Spectrum Analysis, Mass-Gas Chromatography,Gas-Liquid Chromatography-Mass Spectrometry,Mass Spectrometry-Gas Chromatography,Chromatography, Gas Liquid Mass Spectrometry,Chromatography, Gas Mass Spectrometry,Chromatography, Mass Spectrometry-Gas,Chromatography-Mass Spectrometry, Gas,Chromatography-Mass Spectrometry, Gas-Liquid,Gas Chromatography Mass Spectrometry,Gas Liquid Chromatography Mass Spectrometry,Mass Spectrometry Gas Chromatography,Spectrometries, Mass-Gas Chromatography,Spectrometry, Gas Chromatography-Mass,Spectrometry, Gas-Liquid Chromatography-Mass,Spectrometry, Mass Gas Chromatography,Spectrometry-Gas Chromatography, Mass,Spectrum Analysis, Mass Gas Chromatography
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
D002236 Carbohydrate Conformation The characteristic 3-dimensional shape of a carbohydrate. Carbohydrate Linkage,Carbohydrate Conformations,Carbohydrate Linkages,Conformation, Carbohydrate,Conformations, Carbohydrate,Linkage, Carbohydrate,Linkages, Carbohydrate
D002240 Carbohydrate Sequence The sequence of carbohydrates within POLYSACCHARIDES; GLYCOPROTEINS; and GLYCOLIPIDS. Carbohydrate Sequences,Sequence, Carbohydrate,Sequences, Carbohydrate
D002849 Chromatography, Gas Fractionation of a vaporized sample as a consequence of partition between a mobile gaseous phase and a stationary phase held in a column. Two types are gas-solid chromatography, where the fixed phase is a solid, and gas-liquid, in which the stationary phase is a nonvolatile liquid supported on an inert solid matrix. Chromatography, Gas-Liquid,Gas Chromatography,Chromatographies, Gas,Chromatographies, Gas-Liquid,Chromatography, Gas Liquid,Gas Chromatographies,Gas-Liquid Chromatographies,Gas-Liquid Chromatography
D002851 Chromatography, High Pressure Liquid Liquid chromatographic techniques which feature high inlet pressures, high sensitivity, and high speed. Chromatography, High Performance Liquid,Chromatography, High Speed Liquid,Chromatography, Liquid, High Pressure,HPLC,High Performance Liquid Chromatography,High-Performance Liquid Chromatography,UPLC,Ultra Performance Liquid Chromatography,Chromatography, High-Performance Liquid,High-Performance Liquid Chromatographies,Liquid Chromatography, High-Performance

Related Publications

P Mischnick, and B Evers, and J Thiem
Analysis of linkage positions in 2-acetamido-2-deoxy-D-glucopyranosyl residues by the reductive-cleavage method.
December 1986, Carbohydrate research,
P Mischnick, and B Evers, and J Thiem
An improved procedure for the analysis of linkage positions in 2-acetamido-2-deoxy-D-glucopyranosyl residues by the reductive-cleavage method.
January 1994, Carbohydrate research,
P Mischnick, and B Evers, and J Thiem
Benzyl 2-deoxy-alpha-D-arabino-hexopyranoside.
September 1973, Carbohydrate research,
P Mischnick, and B Evers, and J Thiem
Analysis by the reductive-cleavage method of a polysaccharide containing 2-acetamido-2,6-dideoxy-D- and -L-galactopyranosyl residues.
January 1994, Carbohydrate research,
P Mischnick, and B Evers, and J Thiem
Analysis by the reductive-cleavage method of linkage positions in a polysaccharide containing 4-linked D-glucopyranosyluronic residues.
April 1988, Carbohydrate research,
P Mischnick, and B Evers, and J Thiem
Analysis of the linkage positions in D-fructofuranosyl residues by the reductive-cleavage method.
August 1984, Carbohydrate research,
P Mischnick, and B Evers, and J Thiem
Circular dichroism studies of some oligosaccharides containing 2-acetamido-2-deoxy-D-glucopyranose and D-mannopyranose residues.
November 1976, Carbohydrate research,
P Mischnick, and B Evers, and J Thiem
Analysis of linkage positions in a polysaccharide containing nonreducing, terminal alpha-D-glucopyranosyluronic groups by the reductive-cleavage method.
February 1988, Carbohydrate research,
P Mischnick, and B Evers, and J Thiem
A new approach to the synthesis of beta-glycosidically linked oligosaccharides containing 2-acetamido-2-deoxy-D-mannose residues.
June 1985, Carbohydrate research,
P Mischnick, and B Evers, and J Thiem
Structural analysis of sialic acid-containing carbohydrates by the reductive-cleavage method.
October 1993, Carbohydrate research,
Copied contents to your clipboard!