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PubMed1989

Capillary gas-chromatographic analysis of monosaccharides: improvements and comparisons using trifluoroacetylation and trimethylsilylation of sugar O-benzyl- and O-methyl-oximes.

Two new procedures for the gas-chromatographic analysis of monosaccharides are reported. One involves derivatization of the sugars by reaction with O-benzylhydroxylamine followed by trifluoroacetylation with N-methylbis(trifluoroacetamide) and chromatography on a DB-1701 capillary column. This technique probably provides the best resolution achieved to date of the C3-C6 aldoses, as well as of the corresponding alditols. Ketoses can be qualitatively analyzed by this method, but complications interfere with their quantitative analysis. The second procedure also involves initial derivatization as the O-benzyloxime, but is followed by trimethylsilylation with 1-trimethylsilylimidazole, and chromatography on a DB-17 column. This technique is particularly useful for C5 sugars, C6 ketoses, and mixtures of sugars, alditols, and/or lactones. A number of additional, critical, observations on the derivatization and capillary gas-chromatographic analysis of monosaccharides are described.

Acetamides↗

PubMed1985

The use of a monosaccharide linkage group in a heterologous solid-phase enzyme immunoassay for phenytoin.

The preparation is described of monosaccharide-hapten derivatives containing a galactosyl linkage group which bears little structural resemblance to the straight-chain hydrocarbons commonly used for attaching haptens to proteins for use as immunogens. These derivatives are readily synthesised and are coupled to enzymes under mild conditions to produce bridge-heterologous enzyme immunoassays. The use of beta-galactosidase-monosaccharide-phenytoin derivatives in the development of sensitive phenytoin enzyme immunoassays is described and the assays are compared with hapten-heterologous, site-heterologous and homologous phenytoin enzyme immunoassays prepared using other phenytoin derivatives. This technique has application in the development of immunoassays for haptens which have only one functional group to which linkage groups can be attached for covalent coupling of the hapten to proteins.

Animals↗

PubMed1990

Effects of monosaccharides and disaccharides on the formation of food mutagens in model systems.

The formation of the mutagenic imidazoquinoxalines (MeIQx, DiMeIQx) was studied using a modification of a previous model system. Creatine or creatinine (0.9 mmole) was heated together with glycine (0.9 mmole) and various sugars (0.45 mmole) dissolved in diethylene glycol and water (3 ml, 5:1) for up to 15 min at 180 degrees C. This system produced the same amount of mutagenicity after 10 min at 180 degrees C as a previous one during 2 h of reflux boiling at 128 degrees C. MeIQx (4 nmole/mmole creatin(in)e) was the major mutagen produced together with minor amounts of DiMeIQx, both 4,8- and 7,8-DiMeIQx according to HPLC-MS. A few other mutagenic peaks were also separated on HPLC, but they were not identified. Varying the concentration (0-2.4 mmole) and type of monosaccharides and disaccharides greatly affected the yields of all the mutagenic compounds. Sugar in molar amounts lower than the creatin(in)e concentration increased the yield until an optimum was reached. In higher concentrations the formation of all the mutagens was markedly reduced. The same was found for glucose, fructose, sucrose, and lactose, though the monosaccharides showed the most pronounced inhibitory effects. The inhibition of the formation of the mutagenic compounds by an excess of sugars is proposed to be an effect of Maillard reaction products, which may block the formation of imidazoquinoxalines by attacking creatine. Support for this mechanism is given by data showing a lower recovery of unreacted creatine with increasing concentration of glucose and also by an inhibitory effect on the formation of these mutagens after adding a typical Maillard reaction product, 5-hydroxymethyl-2-furfural.

Chromatography, High Pressure Liquid↗

PubMed1987

Mutagenicity of pan-fried bovine tissues in relation to their content of creatine, creatinine, monosaccharides and free amino acids.

The mutagenicity of pan-fried patties of five bovine tissues (meat, heart, tongue, liver and kidney) containing various concentrations of creatine, monosaccharides and free amino acids were studied. Two experiments were performed, one on single tissues fried at 150, 175 or 200 degrees C for 3 min and the other on mixtures of meat and one of the other four tissues in various proportions, fried at 200 degrees C for 3 min. For both experiments, a double-sided Teflon-coated plate was used. Frying at 150 degrees C induced mutagenicity to Salmonella typhimurium strain TA98 only in the heart sample-6000 revertants/100 gE (grams initial raw weight). Meat, heart and tongue fried at 175 or 200 degrees C showed mutagenicity values between 6000 and 19,600 revertants/100 gE. A linear relationship between mutagenicity and temperature was obtained for each of the three muscles and creatine was converted to creatinine with increasing temperature. Liver or kidney samples fried alone showed insignificant mutagenicity at all three temperatures. The creatine plus creatinine levels of raw meat, heart and tongue samples were between 19 and 33 mumol/g wet tissue. Liver and kidney both showed very low amounts of creatine plus creatinine (about 2 mumol/g wet tissue) in the raw tissue, while free amino acids were high. Glucose levels were high in liver but low in kidney samples. In meat/heart and meat/tongue mixtures the mutagenicity varied between 10,800 and 17,300 revertants/100 gE. The meat/liver and meat/kidney mixtures showed linear relationships between mutagenicity and the proportions of the mixture. The values for the slopes and intercepts of the two lines were almost equal. Among the three groups of precursors (creatine plus creatinine, monosaccharides and free amino acids) the creatine plus creatine in raw tissue seems to be the most important for producing mutagenicity. However, in crusts, the creatinine concentration was the variable with which most of the mutagenicity was associated.

Amino Acids↗

PubMed1985

Monosaccharide uptake by erythrocytes of the embryonic and adult chicken.

Rates of monosaccharide uptake by adult and 10-18 day old embryonic chicken erythrocytes were quantitated. The rate of carrier-mediated, stereospecific transport decreased 28% from day 10 to day 14 of incubation and was unchanged thereafter. At no time, however, did the rate of carrier-mediated transport by embryonic erythrocytes differ significantly from that of the adult cells. The rate of transfer by simple diffusion was 3-5 fold faster in embryonic than in adult erythrocytes. Uptake by simple diffusion decreased slightly as the embryo developed. Chronic hyperoxic incubation (70% O2) had little influence on total monosaccharide uptake by embryonic erythrocytes.

3-O-Methylglucose↗

PubMed2005

Detection of bacterial toxins with monosaccharide arrays.

A large number of bacterial toxins, viruses and bacteria target carbohydrate derivatives on the cell surface to attach and gain entry into the cell. We report here the use of a monosaccharide-based array to detect protein toxins. The array-based technique provides the capability to perform simultaneous multianalyte analyses. Arrays of N-acetyl galactosamine (GalNAc) and N-acetylneuraminic acid (Neu5Ac) derivatives were immobilized on the surface of a planar waveguide and were used as receptors for protein toxins. These arrays were probed with fluorescently labeled bacterial cells and protein toxins. While Salmonella typhimurium, Listeria monocytogenes, Escherichia coli and staphylococcal enterotoxin B (SEB) did not bind to either of the monosaccharides, both cholera toxin and tetanus toxin bound to GalNAc and Neu5Ac. The results show that the binding of the toxins to the carbohydrates is density dependent and semi-selective. Both toxins were detectable at 100 ng/ml.

Adsorption↗

PubMed2005

Separation of monosaccharides by hydrophilic interaction chromatography with evaporative light scattering detection.

Hydrophilic interaction liquid chromatography (HILIC) was used to separate monosaccharides that are common in N-linked oligosaccharides in glycoproteins and other compounds. A TSKgel Amide-80 column was eluted with 82% acetonitrile, in 5 mM ammonium formate (pH 5.5). Column temperature was 60 degrees C and evaporative light scattering was used for detection (ELSD). With this method, L-fucose, D-galactose, D-mannose, N-acetyl-D-glucosamine, N-acetylneuraminic acid, and D-glucuronic acid were separated, with detection limits of 0.3-0.5 microg for each monosaccharide, and intermediate precisions were 3-6% RSD (n=6).

Chromatography, Liquid↗

PubMed2004

Growth and enzyme production by three Penicillium species on monosaccharides.

The growth and preference for utilisation of various sugar by the Penicillium species Penicillium pinophilum IBT 4186, Penicillium persicinum IBT 13226 and Penicillium brasilianum IBT 20888 was studied in batch cultivations using various monosaccharides as carbon source, either alone or in mixtures. P. pinophilum IBT 4186 and P. persicinum IBT 13226 had a micro(max) around 0.08-0.09 h(-1) using either glucose or xylose as carbon source. The micro(max) of P. brasilianum IBT 20888 was 0.16 and 0.14 h(-1) on glucose and xylose, respectively. Glucose was found to exert repression on the catabolism of mannose, galactose, xylose and arabinose. The three species were able to utilise all the tested monosaccharides, but arabinose was only slowly metabolised. Glucose was also found to repress the production of endoglucanases, endoxylanases and beta-xylosidases. After glucose depletion, the fungi started producing beta-glucosidase and endoglucanases. Xylose did not repress the enzyme production and it induced the production of endoxylanases and beta-xylosidases.

Fungal Proteins↗

PubMed2004

Adsorption behavior of selected monosaccharides onto an alumina interface.

The adsorption of glucose and fructose from their aqueous solutions onto an alumina interface has been carried out spectrophotometrically at room temperature. The adsorption isotherms are characterized as typical L-type and an adsorption mechanism on the basis of dipolar interactions has been suggested. In addition to this, a partial role of metal-saccharide interactions as found in organometallic complexes (OMCs) for the observed adsorption cannot be ruled out. Various kinetic and thermodynamic parameters of the adsorption process have been evaluated. The effects of variation in experimental conditions of the system have also been investigated. The adsorption exhibited a typical response to the pH effect and maximum adsorption was found near the isoelectric point of alumina (pH 9.0). The anionic addition to the suspension affects the adsorbed amount and Cl(-), SO(4)(2-), and PO(4)(3-) affect the adsorption quantitatively. The addition of similar concentration of cations was found to reduce the adsorbed amount. The presence of cationic and anionic detergents was found to influence both the adsorbed amount and the adsorption rate. The temperature was found to have an inverse effect on adsorption. Adsorptive kinetic parameters have revealed that fructose tends to be a better adsorbate than glucose. This is found to be consistent with the chelation behaviour of monosaccharides as found in the OMC of monosaccharides. The thermodynamics of the adsorption model indicates its spontaneous and exothermic nature. The negative values of entropy are an indication of the probability of a favorable nature of adsorption.

Adsorption↗

PubMed1977

Gas-liquid chromatographic analysis of the monosaccharide composition of acid glycosaminoglycans (mucopolysaccharides) derived from animal tissues.

Quantitative, gas-liquid chromatography was investigated for analysis of the monosaccharide composition of acid mucopolysaccharides from animal tissues. The method entailed the analysis of the trimethylsillyl (Me3Si) derivatives of methyl glycosides on two liquid phases. Good resolution of monosaccharides was achieved by use of columns of SE-30 and Apiezon-M. The procedure was tested with chondroitin 4-sulfate, and the results were slightly different from those of Mathews et al. When the analysis is performed according to this method, important points are: (1) absolutely anhydrous, methanolic hydrogen chloride is necessary, to ensure detection of hexosamines and sialic acid; and (2) high moisture in the air obstructs high recovery of methyl glycosides and their Me3Si derivatives, except in the case of neutral sugars.

Animals↗

PubMed1977

Predicting circular-dichroism spectra of pyranoid monosaccharides.

Fragment spectra are presented that may be summed algebraically to predict the vacuum-ultraviolet, circular-dichroism spectra of certain pyranoid monosaccharides. It is shown that a limited number of these fragment spectra can be used to calculate a larger number of circular-dichroism spectra that had been measured previously. Furthermore, the circular-dichroism spectra of a number of other monosaccharides, whose spectra have not yet been measured, can be predicted.

Circular Dichroism↗

PubMed1986

Identification of pyruvated monosaccharides in polysaccharides by gas-liquid chromatography mass spectrometry.

Twelve bacterial polysaccharides of known structure containing a representative range of pyruvated monosaccharides, were methanolysed, trimethylsilylated, and analysed by g.l.c. and g.l.c.-m.s. Except for 3,4-O-(1-carboxyethylidene)-L-rhamnose, which was unusually labile, the pyruvic acid substituents were largely retained during methanolysis and the Me3Si derivatives of the resulting pyruvated methyl glycosides gave distinctive g.l.c. peaks with characteristic mass spectra. The pyranose rings of 4,6-O-(1-carboxyethylidene)-D-glucose, 4,6-O-(1-carboxyethylidene)-D-mannose, 4,6-O-(1-carboxyethylidene)-D-galactose, and 3,4-O-(1-carboxyethylidene)-D-galactose survived the methanolysis, but that of 2,3-O-(1-carboxyethylidene)-D-glucuronic acid was cleaved to give the methyl ester of 2,3-O-(1-carboxyethylidene)-aldehydo-D-glucuronic acid dimethyl acetal. In the case of 2,3-O-(1-carboxyethylidene)-D-galactose, cleavage of the pyranose ring was less complete; under the conditions used in these experiments two-thirds of the pyranose rings were intact while one-third were cleaved to give the methyl ester of 2,3-O-(1-carboxyethylidene)-aldehydo-D-galactose dimethyl acetal. A very small amount of 3,4-O-(1-carboxyethylidene)-L-rhamnose from one polysaccharide retained its pyruvic acid substituent after gentle methanolysis to give the methyl ester of 3,4-O-(1-carboxyethylidene)-aldehydo-L-rhamnose dimethyl acetal. Susceptibility to cleavage of the pyranose ring during methanolysis appears to be a property of pyruvated monosaccharides with trans-fused 1,3-dioxolane rings.

Chromatography, Gas↗

PubMed1998

Conformational study of synthetic delta 4-uronate monosaccharides and glycosaminoglycan-derived disaccharides.

Sixteen delta 4-uronate monosaccharides were chemically synthesized. Their carboxy group was protected as a methyl or benzyl ester, the anomeric hydroxyl group as a benzyl glycoside and the 2 and 3 hydroxyl groups were protected with different substitution patterns as both ester and ether derivatives. Disaccharides containing delta 4-uronates were prepared from heparin layses. Their carboxy group was unprotected or protected as a benzyl ester and the two hydroxyls in the uronate moiety were free, as O-sulfo derivates or acylated. The conformation of these unsaturated uronate monosaccharide and disaccharide residues was studied using 1H NMR by examining interproton vicinal coupling constants. The delta 4-uronate residue adopted either the 2H1 or the 1H2 conformations. The equilibrium between these two conformers was shown to be controlled by substitution pattern.

Carbohydrate Conformation↗

PubMed2000

Activity coefficients for NaCl-monosaccharide (D-glucose, D-galactose, D-xylose, D-arabinose)-water systems at 298.15 K.

Electrochemical cells with a sodium ion selectivity electrode (Na-ISE) versus a chloride ion selectivity electrode (Cl-ISE) as a reference electrode were used to determine the activity coefficients for NaCl-monosaccharide (D-glucose, D-galactose, D-xylose, and D-arabinose) systems in water at 298.15 K. A comparison of the results thus obtained was made with those determined by another electromotive force (emf) method. It is shown that agreement is excellent. The Gibbs free energy parameters of the interactions between these sugars and NaCl in water were evaluated together with the parameter C1(CHOH, exo), indicating the interaction of the exocyclic CHOH group of saccharide molecules and NaCl. The results suggested that the interactions of these monosaccharides with NaCl are controlled mostly by the dominant conformer of their molecules in water.

Arabinose↗

PubMedDate not supplied

[Evaluation of the role of the monosaccharides, mannose and N-acetylglucosamine in the induction of the acrosome reaction in human spermatozoa].

OBJECTIVE: The aim of this investigation was to evaluate the role of the monosaccharides, mannose and N-acetylglucosamine in the induction of the acrosome reaction in human spermatozoa. METHODS: Each individual gave a semen sample, the samples were capacitated using bovien serum albumin; the analysis of the mannose and N-acetylglucosamine induced acrosome reaction was evaluated for fluorescence microscopy and flow cytometry. RESULTS: The results obtained in the acrosomal reaction in the 10 samples evaluated by flow cytometry showed that only calcium ionophore A23187 induced acrosomal reaction (p < 0.001); in contrast, by fluorescence microscopy, was observed a statistically significant increase in the induced acrosomal reaction with mannose and N-acetylglucosamine (p < 0.001). CONCLUSIONS: The monosaccharides mannose and N-acetylglucosamine induces partial acrosomal reaction and it does not complete, therefore the spermatozoa due to partial acrosomal reaction and the morphologics modifications that suffer during that process is able to fertilize the oocyte.

Acetylglucosamine↗

PubMed2000

Monosaccharide-enriched diets cause hyperleptinemia without hypophagia.

To determine the effect of monosaccharide-enriched diets on plasma leptin and food consumption, body weight, food intake, and serum glucose, insulin, and leptin concentrations were measured in rats maintained on a 10-d course of 60% glucose or 60% fructose diet. The serum leptin concentration in rats fed a high-glucose diet (7.60 +/- 0.6 ng/mL) or a high-fructose diet (5.12 +/- 0.8 ng/mL) was significantly increased compared with that in control rats (2.45 +/- 0.10 ng/mL; P < 0.001). To ascertain that the observed effect was related to hyperinsulinemia, a group of rats were infused with exogenous insulin or rendered insulin resistent with a high-fat diet. When hyperinsulinemia was induced with exogenous infusion, the serum leptin was increased (5.56 +/- 0.23 ng/mL; P < 0.001). High-fat feeding was associated with increased serum leptin (12.1 +/- 1.4 ng/mL) and insulin levels. The increased serum leptin concentration was not associated with decreased food intake. We conclude that monosaccharide-enriched diets, probably through hyperinsulinemia or relative or absolute insulin resistance, cause hyperleptinemia, which does not appear to change feeding behavior.

Animals↗

PubMed1996

Analysis of the binding specificities of oligomannoside-binding proteins using methylated monosaccharides.

The binding specificities of the closely related lectins from Canavalia ensiformis and Dioclea grandiflora were examined using specifically O-alkylated mono- and disaccharides. Both lectins accept any substitution at the monosaccharide C2 hydroxyl group. The binding energy of C2-alkylated ligands-concanavalin A complexes increases by 1 kcal mol-1 for the C2-O-ethyl ligand, while the binding energies of the corresponding complexes with the Dioclea lectin are identical. Both lectins accept methyl, but not ethyl, substitution of the C3 hydroxyl, in contrast to earlier reports. The results are interpreted in terms of existing models of the concanavalin A binding site. While the results are consistent with a model of the concanavalin A extended binding site that places the non-reducing terminus of all disaccharides in the monosaccharide binding site, they point to the dangers of interpreting the binding behavior of unnatural saccharide ligands on the basis of crystallographic data obtained with native ligands.

Binding Sites↗

PubMed2003

Determination of glycosaminoglycan monosaccharides by capillary electrophoresis using laser-induced fluorescence detection.

A newly developed capillary electrophoretic method using laser-induced fluorescence detection (CE-LIF) for the analysis of monosaccharides released from acid hydrolysis of glycosaminoglycans was studied. The method was compared with a previously published method using indirect LIF detection (CE-ILIF). For the CE-LIF method, electrophoretic conditions for the separation of the monosaccharides derivatised with 8-aminopyrene-1,3,6-trisulfonate (APTS) were optimised. The best separations were obtained using 100 mM acetate at pH 4.5 as running buffer. The influence of the injection vial volume on the precision and stability of the sample in different conditions was studied. The detection limits of the CE-LIF method were found to be 0.4-0.6 nM, while those obtained by CE-ILIF ranged from 11.4 to 14.3 microM. Other quality parameters of the method, such as run-to-run precision, day-to-day precision, and linearity were also determined. Finally, the new method was applied to the analysis of the acid hydrolysis products from a glucosaminoglycan (heparin) and a galactosaminoglycan (dermatan sulfate) and cross-contamination between the two solutions was determined. The high sensitivity of the new method allows the determination of dermatan sulfate contaminations in a heparin raw sample down to 0.04% (w/w) and broadens the practical applicability of CE-LIF for the quantitation of the endogenous levels of glycosaminoglycans in animal samples and for pharmacokinetic control after therapeutical heparin administration.

Electrophoresis, Capillary↗