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PubMed1997

Optimization of a polarized photometric detector equipped with a split-type flow cell and its analytical application to oligo-saccharides.

A novel, non-modulated polarimeter called a polarized photometric detector (PPD) was previously described by the authors. The PPD enables the measurement of the optical rotation of chiral compounds as a change in absorbance by placing two linear polarizers on either side of a flow cell of a conventional photometric detector. The present study describes the optimization of the conditions of PPD for highly sensitive detection of saccharides. To maximize the light intensity, the light balancing filter and slit were removed from the detector (Shimadzu model SPD-10AV). These modifications resulted in an approximately 15-fold increase in the incident light intensity when the maximum current was applied to the lamp. When this intense light was transmitted through the polarizers, the signal intensity followed the theoretical equation for phase angles up to around 1 rad. If the energy of the transmitted light was less than 700 mV, however, the baseline noise was too great to determine the chiral analyte accurately. Setting the phase angle between two polarizers at 50 degrees and the detection wavelength at 400 nm provided the most suitable conditions. This detector was applicable for the determinations of oligosaccharides in foodstuffs separated by HPLC using gradient elution.

Flow Injection Analysis↗
PubMed2002

Saccharide display on microtiter plates.

New insight into the importance of carbohydrates in biological systems underscores the need for rapid synthetic and screening procedures for them. Development of an organic synthesis-compatible linker that would attach saccharides to microtiter plates was therefore undertaken to facilitate research in glycobiology. Galactosyllipids containing small, hydrophobic groups at the anomeric position were screened for noncovalent binding to microtiter plates. When the lipid component was a saturated hydrocarbon between 13 and 15 carbons in length, the monosaccharide showed complete retention after aqueous washing and could be utilized in biological assays. This alkyl chain was also successfully employed with more complex oligosaccharides in biological assays. In light of these findings, this method of attachment of oligosaccharides to microtiter plates should be highly efficacious to high-throughput synthesis and analyses of carbohydrates in biological assays.

Carbohydrate Conformation↗
PubMed2000

STAT: a saccharide topology analysis tool used in combination with tandem mass spectrometry.

Sequential stages of mass spectrometry (MSn) have the potential to provide a great deal of structural information in glycan analysis. The saccharide topology analysis tool (STAT) presented here is a Web-based computational program that can quickly extract sequence information from a set of MSn spectra for an oligosaccharide of up to 10 residues. After information such as precursor ion mass, possible monosaccharide moieties, charge carrier, and product ion mass has been input, all possible connectivities are generated and evaluated against the MSn data. The list of possible structures is given a rating based on the likelihood that it is the correct sequence. Examples are given to demonstrate the feasibility of applying STAT to MSn data generated from bacterial lipooligosaccharides and an N-linked glycan. The major advantage of STAT is that the list of possible structures is generated quickly and the rating system pushes the more likely structures to the top of the list. Combining the data generated by STAT with data on the branching patterns of the glycan serves to eliminate all but a handful of structures. These remaining structures could then be used to guide further structural analysis.

Algorithms↗
PubMed2005

LC-MSn methods for saccharide characterization of monoglycosyl flavonoids using postcolumn manganese complexation.

A simple tandem mass spectrometry method for differentiating isomeric monoglycosyl flavonols, flavones, and flavanones using manganese complexation is reported. Dissociation of the [Mn(II) (L) (L - H)]+ and [Mn(II) (L)2 (L - H)]+ species provides unique fragment ions that allow the identification of the saccharide moiety as glucose, galactose, arabinose, or xylose. The glycosylation site of the flavonoid can also be determined by the fragmentation pathways of the Mn complexes. The Mn complexation method was adapted for on-line liquid chromatography-mass spectrometry analysis and tested using flavonoid extracts from Fuji apples (Malus domestica Borkh. cv. Fuji) and red onions (Allium cepa L.). Using fragmentation data obtained from collisional activated dissociation of the deprotonated flavonoid glycosides and their Mn complexes, the major flavonoid species in these extracts were identified.

Chromatography, Liquid↗
PubMedDate not supplied

Water-soluble dendrigrafts bearing saccharidic moieties: elaboration and application to enzyme linked OligoSorbent Assay (ELOSA) diagnostic tests.

The synthesis of a series of water-soluble galactopyranose-functionalized polystyrene-polyvinyl ether dendrigrafts and their characterization (in solution and thin solid deposits) have been achieved. The presence of external galactopyranose groups on dendritic polymers has been exploited to prepare dendrigraft-oligonucleotide conjugates using a simple one-step coupling procedure with amino-ended oligonucleotides (ODNs). Several parameters such as the peripherical density of hydrophilic branches, the polymerization degree of polystyrene or poly(hydroxyethyl vinyl ether) blocks, and the number of galactopyranose groups were tuned. A capture test with short labeled complementary ODNs (25 bases) confirmed the presence of covalently bound ODNs on various kinds of dendrigrafts. The ability of the dendritic polymers to enhance the sensitivity of enzyme-linked oligosorbent assay (ELOSA) diagnostic tests (detection of hepatitis B virus, DNA target of 2400 bases) was then evaluated, especially the influence of the macromolecular architecture and the impact of the structural parameters. The dendrigraft-ODN conjugate with the lower saccharide external density was found to lead to a very significant amplification of the fluorescence signal, corresponding to a limit of sensitivity of 10(9) DNA copies per milliliter (instead of 10(11) DNA copies per milliliter without using dendrigrafts). Conversely, the dendrigrafts exhibiting a very high number of branches and galactopyranose groups at their periphery were not able to induce a better sensitivity due to steric hindrance generated by the peripheral congestion on these polymers.

Dendrimers↗
PubMed1992

Multiple role of hydrophobicity of tryptophan-108 in chicken lysozyme: structural stability, saccharide binding ability, and abnormal pKa of glutamic acid-35.

Trp108 of chicken lysozyme is in van der Waals contact with Glu35, one of two catalytic carboxyl groups. The role of Trp108 in lysozyme function and stability was investigated by using mutant lysozymes secreted from yeast. By the replacement of Trp108 with less hydrophobic residues, Tyr (W108Y lysozyme) and Gln (W108Q lysozyme), the activity, saccharide binding ability, stability, and pKa of Glu35 were all decreased with a decrease in the hydrophobicity of residue 108. Namely, at pH 5.5 and 40 degrees C, the activities of W108Y and W108Q lysozymes against glycol chitin were 17.3 and 1.6% of that of wild-type lysozyme, and their dissociation constants for the binding of a trimer of N-acetyl-D-glucosamine were 7.4 and 309 times larger than that of wild-type lysozyme, respectively. For the reversible unfolding at pH 3.5 and 30 degrees C, W108Y and W108Q lysozymes were less stable than wild-type lysozyme by 1.4 and 3.6 kcal/mol, respectively. As for the pKa of Glu35, the values for W108Y and W108Q lysozymes were found to be lower than that for wild-type lysozyme by 0.2 and by 0.6 pKa unit, respectively. The pKa of Glu35 in lysozyme was also decreased from 6.1 to 5.4 by the presence of 1-3 M guanidine hydrochloride, or to 5.5 by the substitution of Asn for Asp52, another catalytic carboxyl group. Thus, both the hydrophobicity of Trp108 and the electrostatic interaction with Asp52 are equally responsible for the abnormally high pKa (6.1) of Glu35, compared with that (4.4) of a normal glutamic acid residue.(ABSTRACT TRUNCATED AT 250 WORDS)

Animals↗
PubMed1981

Effects of saccharide and salt binding on dimer-tetramer equilibrium of concanavalin A.

The effect of the binding of saccharide ligands on the reversible dimer-tetramer equilibrium on concanavalin A was studied by the high-speed sedimentation equilibrium technique. Both commercial and highly purified fragment-free concanavalin A preparations were used. In the case of the fragment-free preparation, there was no effect of the binding of alpha-methyl mannoside or alpha-methyl glucoside at 35 degrees C and at a variety of conditions of pH and ionic strength. This implies no difference in ligand binding activity between dimeric and tetrameric Con A, in contrast to an earlier report [McKenzie, G. H., & Sawyer, W. H. (1973) J. Biol. Chem. 248, 549-556]. There was a profound effect in the case of the commercial preparation. Dimers that contain hydrolyzed subunits appear to be incompetent to self-associate in the presence of alpha-methyl mannoside or alpha-methyl glycoside, while alpha-methyl galactoside, which does not bind to Con A, had no effect. The effects of very high concentrations of CaCl2 (to 2.5 m) and NaCl (60 6.2 m) were also studied. The data were analyzed by an integrated form of the Tanford extension [Tanford, C. (1969) J. Mol. Biol. 39, 539-544] of the Wyman linked function theory, which includes preferential interactions with salt and water. The integrated form allows preferential interactions to be described as the sum of salt binding and water binding. The data were well described by salt binding alone; it was unnecessary to invoke any water binding effect. The CaCl2 data did indicate that one calcium per subunit of the dimer binds to a site that is buried in the tetramer. This suggests a site on the dimmer-dimer interface which is consistent with Reeke's identification of the protomers composing the solution dimer [Reeke, G. N., Jr., Becker, J. W., & Edelman, G. M. (1975) J. Biol. Chem. 250, 1525-1547].

Calcium↗
PubMed2006

Dendritic saccharide surfactant polymers as antifouling interface materials to reduce platelet adhesion.

Here, we report on the synthesis of dendritic saccharide surfactant polymers as antifouling interface materials to reduce platelet adhesion. An acetal-protected poly(amidoamine) (PAMAM) dendron (5, G = 2) was first synthesized by using aminoacetaldehyde dimethyl acetal (1) as the starting material to provide a monovalent focal structure with dimethyl acetal-protected aldehyde functionality. Maltose dendron (M4, 6) was obtained by reacting the peripheral amine groups of acetal-dendron (5) with maltonolactone. The dendritic surfactant polymers (9) were then synthesized via a two-step method by sequential addition of maltose dendron and hexanal to react with the amine groups on the poly(vinylamine) (PVAm) backbone. Surface activity of the amphiphilic glycopolymers at the air/water interface was demonstrated by reduction in water surface tension. Adsorption of the amphiphilic glycopolymers at the solid/water interface was examined on octadecyltrichlorosilane (OTS)-coated coverslips by water contact angle measurements. A nanoscale understanding of surface-induced self-assembly of the dendritic surfactant polymer on highly oriented pyrolytic graphite (HOPG) was gained using AFM operated in fluid tapping mode. A lateral ordering of adsorbing surfactant polymer was visualized with a pattern in strands 60 degrees out of alignment. The static platelet adhesion tests show that the hexyl side chains can facilitate adsorption of the surfactant polymers onto hydrophobic substrates, while the maltose dendron side chains can provide a dense canopy of protective glycocalyx-like layer as an antifouling interface to reduce platelet adhesion.

Adsorption↗
PubMed1999

DSC confirmation that vitrification is not necessary for stabilization of the restriction enzyme EcoRI dried with saccharides

The glass transition temperature (Tg) of preparations of the restriction enzyme EcoRI, vacuum-dried in the presence of sucrose, trehalose, or raffinose, was determined using differential scanning calorimetry. Tg values were well below those expected for low-moisture sucrose, trehalose, or raffinose, and this was attributed to the presence of glycerol (a plasticizer), which was a main component of the restriction enzyme preparation. This was verified by determining the glass transition temperature of glycerol, which was found to be (onset value) -77 degrees C. Present results confirmed that vitrification (i.e., glass formation) was not necessary for enzyme protection in present low-moisture saccharide systems. As shown in previous work, enzyme EcoRI was very stable stored at 37/45 degrees C in spite of the fact that sugar matrices were completely rubbery, as unequivocally demonstrated in the present work.

Journal Article↗
PubMedDate not supplied

The Concise Connection Table: collected definitions with extensions for stereochemistry and saccharides.

The Concise Connection Table is a representation of molecular structures based on an implicit hierarchy of substructural components. This paper introduces a number of enhancements and extensions to the original definition, particularly relating to representations of stereochemistry and saccharides, and summarizes the overall principles of the CCT in one definitive presentation.

Carbohydrate Sequence↗
PubMed2002

Potentiometric saccharide detection based on the pK(a) changes of poly(aniline boronic acid).

A novel approach for the potentiometric detection of saccharides using poly(aniline boronic acid) is presented. A model is described in which the electrochemical potential is sensitive to the change in the pK(a) of the conducting polymer as a result of boronic acid-diol complexation. In this system, boronic acid complexation is the mode of transduction and it is manifested as changes in the electrochemical potential of the polymer with remarkable selectivity. Characteristics of both transient and steady-state response associated with the complexation are discussed. The presence of Nafion and fluoride during the electrochemical polymerization of 3-aminophenylboronic acid are shown to impact the sensitivity and the stability of the electrode response. The sensor sensitivity is improved significantly by increasing the concentration of sodium fluoride during the polymerization. Finally, the nature of the selectivity of the boronic acid-diol reaction under these conditions is explored by using molecular orbital calculations.

Aniline Compounds↗
PubMed2003

Covalently attached saccharides on silicon surfaces.

This paper presents the first functionalization of silicon surfaces with well-defined, covalently attached monolayers containing saccharides. Two methods were used to this aim: a thermal method (refluxing in mesitylene) and a recently developed, extremely mild photochemical method (irradiation with 447 nm at room temperature). The results were analyzed by FT-IR and angle-resolved X-ray photoelectron spectroscopy. The use of a two-dimensional detector in ARXPS allows for unparalleled, subnanometer resolution in the determination of the elemental composition of monolayers. Even for monolayers with a total thickness of only approximately 1.5 nm, a clear elemental depth profile can be obtained. Such analyses display for sialic acid-containing monolayers that the mild photochemical attachment does not destroy the (rather fragile) sialic acid moiety and that the sugar is present at the top of the monolayer and thus available for biological interactions.

Alkanes↗
PubMed2004

Hydrogen bonded oligohydrazide foldamers and their recognition for saccharides.

This paper describes the synthesis and characterization of the first series of hydrogen bonding-driven hydrazide foldamers and their recognition for alkyl saccharides in chloroform. Oligomers 1, 2-4, 5, 6, and 7, which contain one, two, four, six, or twelve repeated dibenzoyl hydrazide residues, respectively, have been prepared. The rigid and planar conformations of 1 and 2 or 4 have been established with X-ray analysis and (1)H NMR spectroscopy, whereas the folding and helical conformations of 5-7 have been evidenced by the 1D and 2D (1)H NMR and IR spectroscopy and molecular mechanics calculations. Molecular mechanics calculations also revealed that 5, 6, and 7 possess a rigid cavity with size of ca. 10.6 to 11.1 A, and half of the carbonyl groups in the folding conformations are orientated inwardly inside the cavity. (1)H NMR and CD experiments revealed that 5-7 efficiently complex alkylated mono- and disaccharides 32-35 in chloroform. The association constants (K(assoc)) of the complexes have been determined with the (1)H NMR and fluorescent titration methods. The energy-minimized conformation of 6.34 has been obtained with molecular mechanics calculation. The hydrazide-based folding structures described here represent novel examples of hydrogen bonding-driven foldamers that act as artificial receptors for selective molecular recognition.

Carbohydrate Conformation↗
PubMed2006

Stereochemical and regiochemical trends in the selective detection of saccharides.

Several discreet sugar-boronate complexes exist in solution. This is due to the complex equilibria between isomeric species of even the simplest monosaccharides. In the current investigation, we determine the regio- and stereochemical features of the various equilibrating sugar isomers that induce signal transduction in boronic acid chemosensors such as 1 as well as 2 and 3. We present a unique example of a chemosensor (1) that is selective for ribose, adenosine, nucleotides, nucleosides, and congeners. As a result of this study, we are able to predict and achieve selective fluorescence and colorimetric responses to specific disaccharides as a consequence of their terminal sugar residue linkage patterns and configurations. We also find that the combined use of chemosensors exhibiting complementary reactivities may be used cooperatively to obtain enhanced selectivity for ribose and rare saccharides.

Adenosine↗
PubMed2004

Quantification of saccharides in multiple floral honeys using fourier transform infrared microattenuated total reflectance spectroscopy.

Fourier transform infrared (FTIR) spectroscopy with microattenuated total reflectance (mATR) sampling accessory and chemometrics (partial least squares and principal component regression) was used for the simultaneous determination of saccharides such as fructose, glucose, sucrose, and maltose in honey. Two calibration models were developed. The first model used a set of 42 standard mixtures of fructose, glucose, sucrose, and maltose prepared over the range of concentrations normally present in honey, whereas the second model used a set of 45 honey samples from various floral and regional sources. The developed models were validated with different data sets and verified by high-performance liquid chromatography (HPLC) measurements. The R (2) values between the FTIR-mATR predicted and HPLC results of the different sugars were between 0.971 and 0.993, demonstrating the predictive ability and accuracy of the procedure.

Carbohydrates↗
PubMed2004

Substituent effects on monoboronic acid sensors for saccharides based on N-phenyl-1,8-naphthalenedicarboximides.

In the course of our investigations on new monoboronic acid saccharide sensors with C(0) spacers, a series of probes 1-6 based on 1,8-naphthalenedicarboximide were synthesized. Sensor 1 displays features typical of PET monoboronic acid sensors and shows high selectivity to fructose. Sensor 2 exhibits a novel dual emission and remarkable sensitivity for glucose relative to fructose and galactose through subtle changes in pH. Sensor 3 displays significantly enhanced fluorescence in the presence of galactose at low pH. Although probes 4-6 exhibit unique properties such as high quantum yield (Phi(F) = 0.407) and excellent solubility in water, they did not show significant change in fluorescence intensity in the presence of monosaccharides. The effects of substituent on all six probes lend support to the proposed photoelectrochemical model.

Biosensing Techniques↗
PubMed2006

Binding of 8-anilinonaphthalene sulfonate to dimeric and tetrameric concanavalin A: energetics and its implications on saccharide binding studied by isothermal titration calorimetry and spectroscopy.

The binding of 8-anilinonaphthalene sulfonate to concanavalin A has been investigated. Isothermal titration calorimetry (ITC) and circular dichroism studies have been performed under different experimental conditions to understand the binding quantitatively and evaluate contributions of different forces responsible for it. Isothermal titration calorimetric results of concanavalin A with ANS at pH 5.2 and 2.5, where it exists as a dimer, indicated binding heterogeneity and two classes of noninteracting sites. Enhancement of the binding constants from native to pH 2.5 suggests that the ANS binding is strongly influenced by the protein charge and the favorable alteration in the structure of concanavalin A as suggested by near-UV CD results. No binding was observed with the tetrameric form of concanavalin A, indicating shielding of sites due to dimerization of canonical dimers. The results have also demonstrated existence of a hydrophobic binding site that is distinct from the saccharide binding site.

Anilino Naphthalenesulfonates↗