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PubMed1986

Rapid method for determining desmosine, isodesmosine, 5-hydroxylysine, tryptophan, lysinoalanine and the amino sugars in proteins and tissues.

A rapid and sensitive chromatographic method is described for determining desmosine, isodesmosine, 5-hydroxylysine, tryptophan, lysinoalanine, glucosamine and galactosamine at picomole levels in protein and tissue hydrolysates. This method uses either an automated amino acid analyser with a 17.5 X 0.28 cm microcolumn packed with 6.0 +/- 0.5 micron spherical resin, thermostated at 52 degrees C, one buffer system (0.21 M sodium citrate, pH 5.125) and 3-nitrotyrosine as the internal standard, or conventional instruments using the same system but with larger diameter columns and resins (11.0 +/- 1.0 micron). This method should be especially valuable for determining collagen and elastin in tissue hydrolysates from the amounts of 5-hydroxylysine, and desmosine or isodesmosine present, respectively, and for studying protein hydroxylation, glycosylation, cross-linking formation, and the turnover rates of collagen and elastin in normal and diseased tissues.

Amino Acids↗
PubMed2002

Some amino sugars structurally related to 6-deoxymannojirimycin precursors prepared from methyl 6-deoxy-2,3-O-isopropylidene-alpha-D-lyxo-hexofuranosid-5-ulose and methyl 2,3-O-isopropylidene-alpha-D-lyxo-pentodialdo-1,4-furanoside.

Methyl (5S)-5-C-amino-5-cyano-5-deoxy-2,3-O-isopropylidene-alpha-D-lyxofuranoside has been synthesised from methyl 2,3-O-isopropylidene-alpha-D-lyxo-pentodialdo-1,4-furanoside, applying the Strecker synthesis. Analogously, methyl (5S) and (5R)-5-C-amino-5-cyano-5,6-dideoxy-2,3-O-isopropylidene-alpha-D-lyxo-hexofuranosides were prepared from methyl 6-deoxy-2,3-O-isopropylidene-alpha-D-lyxo-hexofuranosid-5-ulose. The 5-S configuration was unambiguously determined by single-crystal X-ray diffraction analysis of corresponding N-acetyl derivatives. Conformations of five-membered rings are discussed. The conversion of N-acetylated amino nitriles to N-acetylamino acid ethyl ester and amide, respectively, is also described.

1-Deoxynojirimycin↗
PubMed1978

The 4-amino sugars present in the lipopolysaccharides of vibro cholerae and related vibrios.

Brief treatment, with 10 M hydrochloric acid, of the lipopolysaccharides of Vibrio cholerae and related organisms led to the release of 4-amino-4, 6-dideoxy-D-mannose (D-perosamine) and 4-amino-4-deoxyl-L-arabinose. These sugar are highly unstable and undergo complex changes in neutral and basic media. Of the strains examined, the lipopolysaccharides from representatives of the Inaba group contain only D-perosamine, while those of the Ogawa biotype have 4-amino-4-deoxyl-L-arabinose as an additional component. The other Vibrios produce lipopolysaccharides which lack these sugars.

Amino Sugars↗
PubMed1996

N-Tetrachlorophthaloyl (TCP) for ready protection/deprotection of amino sugar glycosides.

The tetrachlorophthaloyl (TCP) group can be utilized when imidic protection of an amine is desired and durability of the protecting group to conditions ranging from mildly basic to harshly acidic is required. Installation can be accomplished in two steps by treating the free base with the commercially available TCP anhydride, and then closing the imidic ring with acetic anhydride and pyridine. Cleavage is effected by 2-4 eq of ethylenediamine under very mild conditions under which esters and glycopeptides have been shown to be stable, and racemization of amino acid residues does not occur. Unsubstituted phthalimides, even within the same molecule, are also unaffected during TCP cleavage. TCP protecting groups serve as beta-directors on donors and can also be present on acceptor species during electrophilic couplings in oligosaccharide synthesis.

Amino Sugars↗
PubMed1990

Plagiarizing plants: amino sugars as a class of glycosidase inhibitors.

Many polyhydroxylated alkaloids from plants are specific inhibitors of glycosidases. Information about these has led to the development of a wide range of both naturally occurring and synthetic inhibitors which may be used for mechanistic studies and for the purification of these enzymes. Sugar lactones are starting materials for highly efficient syntheses of deoxymannojirimycin and deoxyfuconojirimycin and of a number of their iminoheptitol analogues. This has allowed an investigation of the relationship between mannosidase and fucosidase inhibition.

1-Deoxynojirimycin↗
PubMed1987

[3-(3-hydroxy-2,3-dimethyl-5-oxoprolyl)amino-3,6-dideoxy-D-glucose: a new amino sugar of the antigenic polysaccharide from Pseudomonas fluorescens].

O-specific polysaccharide chain of the Pseudomonas fluorescens lipopolysaccharide is composed of 6-deoxy-L-talose, N-acetyl-D-fucosamine and N-acyl-3,6-dideoxy-D-glucose. Analysis of the latter sugar, obtained from the polysaccharide hydrolysate, by 1H NMR (including NOE), 13C NMR, and FAB mass spectrometry proved the unusual N-acyl substituent to be a 3-hydroxy-2,3-dimethyl-5-oxoproline residue.

Amino Sugars↗
PubMed1983

Amino-sugars enhance recognition and phagocytosis of particles by human neutrophils.

Neutrophils were examined for their ability to recognize and ingest beads coated with amino-derivatives of glucose, mannose, and galactose. Radioactive or fluorescent beads coated with any of the three sugars were ingested to an extent three times that observed with albumin-coated beads. Enhancement of ingestion of sugar-coated beads was much more evident when examined by electron micrographic studies. Inclusion of glucose or mannose in the medium with glucose- or mannose-coated beads caused a dose-dependent reduction of ingestion to control levels, but ingestion of galactose-coated beads was poorly inhibited. Similarly, galactose or fucose (6-deoxy-galactose) markedly inhibited ingestion of galactose-coated beads, but caused only a slight decrease in ingestion of glucose- or mannose-coated beads. Thus, neutrophils possess carbohydrate-binding membrane structures that can mediate recognition and ingestion of sugar-coated beads. Such carbohydrate recognition systems may underlie certain interactions of neutrophils and other surfaces.

Amino Sugars↗
PubMed1968

Determination of amino sugars in mixtures containing glucosamine, galactosamine and muramic acid.

A colorimetric method is described whereby the direct quantitative determination of glucosamine, galactosamine and muramic acid can be achieved without previous treatment of the cell-wall hydrolysate, for example by column chromatography. Molar ratios of hexosamines in cell-wall preparations, from a number of bacterial species, determined by this method were found to be in general agreement with previously published results.

Amino Sugars↗
PubMed1975

Active antitumor components in a decomposed amino sugar I: Effect of sugar structure on activity.

While pure methyl 5-(2-chloroethylamino)-5-deoxy-2,3-O-isopropylidene-beta-D-ribofuranoside hydrochloride has no L-1210 leukemia activity, a decomposed sample was found to be very active. One of several approaches taken to determine the nature of the active component involved a study of how sugar structure affects antitumor activity. A number of aminoribose derivatives were prepared and tested against the murine L-1210 and P-388 leukemia and the B-16 melanoma tumor systems. Compounds were tested as pure materials and as synthetically degraded mixtures. Both the beta-haloethyl group and a secondary amine were required for highest activity.

Amino Sugars↗
PubMedDate not supplied

[Determination of cell wall amino sugars in Streptococcus on a carbohydrate analyzer].

A method of determining aminosaccharides (muramic acid, glucosamine and galactosamine) by means of a carbohydrate analyzer "Biotronic" using the cation-exchange resin DC-6 A ("Durrum") was developed. Chromatographic conditions correspond to the conditions of neutral sugar analysis on a column with DCh-4 resin, that enables after a slight modification of the analyzer to pass from the determining of aminosaccharides to the determining of neutral sugars. The method was used for determining the carbohydrate composition of streptococcus cell walls. The results obtained allow to conclude that using this method one can get more information on the hydrocarbon composition of various biological objects than using the method of aminosaccharide determining by means of aminoacid anylyzer, which is widely in practice nowadays.

Amino Sugars↗
PubMed2003

Synthesis of new branched-chain amino sugars.

1,3-Dipolar cycloaddition of methylideneaniline N-oxide to sugar enones is described. The addition occurred exclusively from the side opposite to the aglycone affording the corresponding alkyl alpha-D-lyxo-hexopyranosid-(2,3:5',4')-phenylisoxazolidin-4-uloses. Hydrogenation of these compounds readily yielded the corresponding alkyl 3-deoxy-3-N-phenylaminomethyl-alpha-D-talopyranoside, that were readily transformed to the acetates. The structure and conformation of the bicyclic compounds were determined by 1H NMR studies and semi-empirical molecular orbital calculations employing the AM1 method.

Amino Sugars↗
PubMed1969

Biosynthesis of amino sugars by Pseudomonas saccharophila.

Pseudomonas saccharophila growing on specifically labeled glucose incorporated isotope into cell wall glucosamine and muramic acid with less than 5% randomization of carbons. Glucosamine contained isotope in both the 1 and 6 positions when cells were grown on either galactose-6-(14)C or gluconate-6-(14)C. With galactose-1-(14)C, only muramic acid was labeled. Specific activities of the carboxyl group of muramic acid obtained from the glucose-grown cells did not indicate whether the origin of the side chain of muramic acid is pyruvate or phosphoenolpyruvate. However, the high specific activity obtained from galactose-1-(14)C suggested that induced cells preferentially incorporate C-1 of galactose into the side chain of muramic acid. Addition of unlabeled glucosamine to growing cultures repressed incorporation of substrate isotope into glucosamine, but muramic acid contained activity in the lactyl side chain.

Amino Sugars↗