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Journal articles on the topic 'Saccharide derivatives'

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Author: Grafiati

Published: 10 March 2023

Last updated: 11 March 2023

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1

Fujishima, Masaki, Kensuke Furuyama, Yojiro Ishihiro, Shuichi Onodera, Eri Fukushi, Noureddine Benkeblia, and Norio Shiomi. "Isolation and Structural Analysis In Vivo of Newly Synthesized Fructooligosaccharides in Onion Bulbs Tissues (Allium cepa L.) during Storage." International Journal of Carbohydrate Chemistry 2009 (June 18, 2009): 1–9. http://dx.doi.org/10.1155/2009/493737.

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Fructooligosaccharides are involved in physiological activities and quality attributes of onion bulbs. This work describes structures of newly synthesized oligosaccharides formed by fructose moieties in onion bulb tissues during storage. Onion bulbs were stored for four weeks at 10. HPAEC-PAD analysis showed that saccharide 1 was eluted after 1-kestose while saccharide 2 was eluted after nystose . Saccharides 1 and 2 have R-sucrose values of 1.55 and 2.15 by HPAEC, a reducing terminal, a reducing sugar-to-fructose ratio of 0.5 and 0.3, and a degree of polymerization of 2 and 3 by TOF-MS, respectively. GLC analysis of the methyl derivatives and NMR measurement of the saccharides confirmed the presence of two different structures: the structure of saccharide 1 is composed by two fructose moieties and linked by linkage and was identified as inulobiose [-D-fructofuranosyl---D-fructopyranose]. The structure of saccharide 2 consists of three units of fructose linked by linkage and was identified as inulotriose [-D-fructofuranosyl---D-fructofuranosyl---D-fructopyranose]. The spectra also showed that 70 to 80% of the terminal fructose residue of the two saccharides is of pyranosyl form, while 20 to 30% is of furanosyl form. This finding demonstrated that these newly produced saccharides, catalyzed by onion-purified 6G-FFT, were synthesized by the action of 1-FFT fructosyltransfer from 1-kestose to free fructopyranose yielding inulobiose and sucrose, while elongation of fructofuranosyl units occurs at this transferred fructofuranosyl residue to produce inulooligosaccharide having an additional unit of fructofuranose.

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2

Hung, Wei-Ting, Yi-Ting Chen, Chung-Hsuan Chen, Yuan Chuan Lee, Jim-Min Fang, and Wen-Bin Yang. "Flow Chemistry System for Carbohydrate Analysis by Rapid Labeling of Saccharides after Glycan Hydrolysis." SLAS TECHNOLOGY: Translating Life Sciences Innovation 25, no. 4 (June 19, 2020): 356–66. http://dx.doi.org/10.1177/2472630320924620.

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This study demonstrates the utilization of a flow chemistry system for continuous glycan hydrolysis and saccharide labeling to assist with the existing methods in glycan structural analysis. Acidic hydrolysis of glycans could be accelerated in a flow system. Aldoses and α-ketoacid-type saccharides were effectively labeled with naphthalene-2,3-diamine (NADA) at 60 °C for 10 min to form the fluorescent naphthimidazole (NAIM) and quinoxalinone (QXO) derivatives, respectively. The NADA-labeled derivatives improved the structural determination and composition analysis for their parent saccharides by using matrix-assisted laser desorption ionization time-of-flight mass spectrometry (MALDI-TOF-MS), liquid chromatography mass spectrometry (LC-MS), and nuclear magnetic resonance (NMR). Furthermore, this protocol was applied to determine the SA–Gal–Glc sequence of GM3-sugar out of six possible permutations.

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3

İ MAHMOOD, Israa, Salih SALMAN, and Luma ABD. "New Bioactive Aromatic Heterocyclic Macromolecules with Monosaccharide Core." Journal of the Turkish Chemical Society Section A: Chemistry 9, no. 3 (August 31, 2022): 889–900. http://dx.doi.org/10.18596/jotcsa.1098055.

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1,1,2-trimethyl-1H-benzo[e]indole is an important heterocyclic compound, its available in reasonable price and can easily modified to make a good intermediate for other derivatives. That is quite enough reasons to use as starting material for a new series of compounds with other biomolecules such as monosaccharides after simple modification. The target molecules show biological activity. So, the current work is aiming to improve the activity and the properties of the benzo indole by attaching with a naturally occurring, and biodegradable compounds represented by 2-deoxy-2-amino -d-glucose and 6-deoxy-6-amino-d-glucose to synthesis both mono and di-saccharides derivatives of benzo indole. Two steps synthesis were used for mono-saccharide derivatives and three steps for di-saccharide derivatives, the first is the functionalization of 1,1,2-trimethyl-1H-benzo[e]indole [1] via the reaction with POCl3 to produce 2-(1,1-dimethyl-1H-benzo[e]indol-2(3H)-ylidene) malonaldehyde [2] with two aldehydes reaction centers, while in the second step the latter was coupled with sugar via amino groups to get the two monosaccharide derivatives [3,5], while the disaccharides molecules [4,6] taken one more step with harder conditions to overcome the steric hindrance at the other reaction center. The purity and characterization of the target molecules was confirmed using spectroscopy methods including 1H NMR and 13 NMR. The synthesized compound shows a good biological activity as antibacterial antifungal.

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4

Yuan, Dan, Xuewen Du, Junfeng Shi, Ning Zhou, Abdulgader Ahmed Baoum, and Bing Xu. "Synthesis of novel conjugates of a saccharide, amino acids, nucleobase and the evaluation of their cell compatibility." Beilstein Journal of Organic Chemistry 10 (October 16, 2014): 2406–13. http://dx.doi.org/10.3762/bjoc.10.250.

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This article reports the synthesis of a novel type of conjugate of three fundamental biological build blocks (i.e., saccharide, amino acids, and nucleobase) and their cell compatibility. The facile synthesis starts with the synthesis of nucleobase and saccharide derivatives, then uses solid-phase peptide synthesis (SPPS) to build the peptide segment (Phe-Arg-Gly-Asp or naphthAla-Phe-Arg-Gly-Asp with fully protected groups), and later, an amidation reaction in liquid phase connects these three parts together. The overall yield of these multiple step synthesis is about 34%. Besides exhibiting excellent solubility, these conjugates of saccharide–amino acids–nucleobase (SAN), like the previously reported conjugates of nucleobase–amino acids–saccharide (NAS) and nucleobase–saccharide–amino acids (NSA), are mammalian cell compatible.

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5

Klein, J., M. Kraus, M. Tich�, B. Zelezn�, V. Jon�kov�, and J. Kocourek. "Water-soluble poly(acrylamide-allylamine) derivatives of saccharides for protein-saccharide binding studies." Glycoconjugate Journal 12, no. 1 (February 1995): 51–54. http://dx.doi.org/10.1007/bf00731868.

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6

Ćwik, Paweł, Patrycja Ciosek-Skibińska, Marcin Zabadaj, Sergiusz Luliński, Krzysztof Durka, and Wojciech Wróblewski. "Differential Sensing of Saccharides Based on an Array of Fluorinated Benzosiloxaborole Receptors." Sensors 20, no. 12 (June 22, 2020): 3540. http://dx.doi.org/10.3390/s20123540.

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Fluorinated benzosiloxaboroles–silicon congeners of benzoxaboroles, were synthesized and tested as molecular receptors for mono- and disaccharides. The receptors differed in the Lewis acidity of the boron center as well as in the number of potential binding sites. The calculated stability constants indicated different binding affinity of benzosiloxaborole derivatives towards selected saccharides, enabling their classification using a receptor array-based sensing. Unique fluorescence fingerprints were created on the basis of competitive interactions of the studied receptors with both Alizarin Red S (ARS) and tested saccharide molecules. Detailed chemometric analysis of the obtained fluorescence data (based on partial least squares-discriminant analysis and hierarchical clustering analysis) provided the differential sensing of common saccharides, in particular the differentiation between glucose and fructose. In addition, DFT calculations were carried out to shed light on the binding mechanism under different pH conditions.

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7

Bashir, Sajid, Peter J. Derrick, Peter Critchley, Paul J. Gates, and James Staunton. "Matrix-Assisted Laser Desorption/Ionization Time-of-Flight Mass Spectrometry of Dextran and Dextrin Derivatives." European Journal of Mass Spectrometry 9, no. 1 (February 2003): 61–70. http://dx.doi.org/10.1255/ejms.510.

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Application of matrix-assisted laser desorption/ionization (MALDI) to the analysis of dextran and dextrin derivatives, specifically glucose saccharides, by time-of-flight (TOF) mass spectrometry is reported. MALDI-TOF analysis was carried out on alpha-, beta-and gamma-cyclodextrin, two O-methylated beta-cyclodextrins of differing degrees of substitution (DS) and dextrans (a linear glucose saccharide), as pure and doped solutions and as mixtures of two or more of these analytes. Doping was carried out with trace amounts of inorganic salts. The purpose of the analysis of the cyclodextrins was to determine whether they would form inclusion complexes with the various added cations, or whether less specific cation addition/exchange was occurring either prior to desorption or in the gas phase.

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8

McGregor, Nicholas, Christophe Pardin, and W. G. Skene. "Using Quenching Kinetics and Thermodynamics of Amino-Fluorophores as Empirical Tools for Predicting Boronic Acid Sensors Suitable for Use in Physiological Conditions." Australian Journal of Chemistry 64, no. 11 (2011): 1438. http://dx.doi.org/10.1071/ch11297.

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A series of water-soluble 1-amino-naphthalenes and 2-amino-fluorenes are prepared. These serve as model fluorophores for measuring the thermodynamics and kinetics of fluorescence quenching with phenylboronic acids and aliphatic amines. Steady-state and time-resolved fluorescence quenching kinetics are investigated using the Stern–Volmer method. Diffusion limited quenching constants and exergonic thermodynamics of electron transfer are derived for the 5-amino-1-napthol and 2-aminofluorene derivatives with phenylboronic acid and/or an aliphatic imine. No quenching and endergonic thermodynamics or electron transfer are observed for 5-sulfonamide, 5-sulfonic acid, or 5-hydroxy-7-sulfonic acid aminonaphthalene derivatives. Boronic acid sensors synthesized from these aminofluorophores by reductive amination with 2-formylphenylboronic acid undergo fluorescence revival in the presence of saccharides only when the fluorophore demonstrates diffusion limited quenching kinetics and exergonic thermodynamics of electron transfer with the boronic acid or imine quenchers. Thus, these two properties are suitable empirical tools for predicting saccharide-induced fluorescence revival of boronic acid sensors.

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9

Jackson, P. "The use of polyacrylamide-gel electrophoresis for the high-resolution separation of reducing saccharides labelled with the fluorophore 8-aminonaphthalene-1,3,6-trisulphonic acid. Detection of picomolar quantities by an imaging system based on a cooled charge-coupled device." Biochemical Journal 270, no. 3 (September 15, 1990): 705–13. http://dx.doi.org/10.1042/bj2700705.

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Various monosaccharides, oligosaccharides and small polysaccharides were labelled covalently at their reducing end groups with the fluorophore 8-aminonaphthalene-1,3,6-trisulphonic acid (ANTS), and the resulting fluorescent derivatives were separated by high-resolution PAGE. The electrophoretic mobilities of the labelled saccharides are related largely to the compounds' Mr values, but they are also influenced by the individual chemical structures of the saccharides. Various positional isomers and some epimers, for instance galactose and glucose, were resolved. Oligosaccharide and small polysaccharide derivatives, prepared from an enzymic digest of starch, each differing in size by a single hexose residue and with a range of degrees of polymerization from 2 to 26, were all resolved in a single gel. The method was relatively rapid and simple to perform. It enabled multiple samples to be analysed in parallel with high sensitivity. The fluorescent-labelling procedure was virtually quantitative. As little as 1 pmol of ANTS-labelled saccharide was detected photographically when the gels were illuminated by u.v. light. When the gels were viewed using an imaging system based on a cooled charge-coupled device, as little as 0.2 pmol was detected. The method may be useful for the structural analysis of the carbohydrate moieties of glycoconjugates and other naturally occurring oligosaccharides.

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10

Menuel, S., B. Léger, A. Addad, E. Monflier, and F. Hapiot. "Cyclodextrins as effective additives in AuNP-catalyzed reduction of nitrobenzene derivatives in a ball-mill." Green Chemistry 18, no. 20 (2016): 5500–5509. http://dx.doi.org/10.1039/c6gc00770h.

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At the boundary between mechanochemistry, supramolecular chemistry and catalysis, the present study explores the role of cyclodextrins (CDs) and other saccharide additives in the mechanosynthesis of gold nanoparticles (AuNPs) and their use as catalysts in the reduction of substituted nitrobenzene derivatives.

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11

Zhang, Zuo-Peng, Ye Zhong, Zhen-Bin Han, Lin Zhou, Hua-Sheng Su, Jian Wang, Yang Liu, and Mao-Sheng Cheng. "Synthesis, Molecular Docking Analysis and Biological Evaluations of Saccharide-Modified Thiadiazole Sulfonamide Derivatives." International Journal of Molecular Sciences 22, no. 11 (May 22, 2021): 5482. http://dx.doi.org/10.3390/ijms22115482.

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A series of saccharide-modified thiadiazole sulfonamide derivatives has been designed and synthesized by the “tail approach” and evaluated for inhibitory activity against carbonic anhydrases II, IX, and XII. Most of the compounds showed high topological polar surface area (TPSA) values and excellent enzyme inhibitory activity. The impacts of some compounds on the viability of HT-29, MDA-MB-231, and MG-63 human cancer cell lines were examined under both normoxic and hypoxic conditions, and they showed certain inhibitory effects on cell viability. Moreover, it was found that the series of compounds had the ability to raise the pH of the tumor cell microenvironment. All the results proved that saccharide-modified thiadiazole sulfonamides have important research prospects for the development of CA IX inhibitors.

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12

Parrot-Lopez, Héléne, Eric Leray, and Anthony W. Coleman. "New β-cyclodextrin derivatives possessing biologically active saccharide antennae." Supramolecular Chemistry 3, no. 1 (December 1993): 37–42. http://dx.doi.org/10.1080/10610279308029836.

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13

Kassab, Rima, Caroline Felix, Hélène Parrot-Lopez, and Roger Bonaly. "Synthesis of Cyclodextrin Derivatives Carrying Bio-Recognisable Saccharide Antennae." Tetrahedron Letters 38, no. 43 (October 1997): 7555–58. http://dx.doi.org/10.1016/s0040-4039(97)10033-8.

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14

Papacchini, A., M. R. Telaretti Leggieri, L. Zucchini, M. A. Ortenzi, F. Ridi, D. Giomi, and A. Salvini. "Modified α,α′-trehalose and d -glucose: green monomers for the synthesis of vinyl copolymers." Royal Society Open Science 5, no. 5 (May 2018): 171313. http://dx.doi.org/10.1098/rsos.171313.

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Allyl saccharide/vinyl copolymers were synthesized using renewable feedstocks (α,α′-trehalose and d -glucose) to obtain ‘green monomers’. Properly designed synthetic procedures were used to obtain copolymers with high purity and without protection/deprotection steps in agreement with the principles of green chemistry and industrial sustainability. The use of saccharide derivatives as monomers allowed products to be obtained that showed high affinity and compatibility for the cellulosic substrates, like paper or wood, and that were suitable for applications like adhesion or consolidation in the field of cultural heritage. All reaction products were characterized by FT-IR and NMR spectroscopies and SEC analyses, while thermal properties were evaluated by DSC analyses.

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15

Klein, Joachim, Markwart Kunz, and Lutz Guderjahn. "New amphiphilic copolymers derived from hydrophobically modified vinyl saccharides." Canadian Journal of Chemistry 73, no. 11 (November 1, 1995): 1941–47. http://dx.doi.org/10.1139/v95-239.

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The synthesis and characterization of new amphiphilic copolymers derived from copolymerization of hydrophobically modified so-called vinyl saccharides with 1-vinyl-2-pyrrolidone are described. The vinyl saccharides were prepared in a two-step synthesis. In the first step hydrophobically modified saccharide derivatives were synthesized without protecting procedures by direct reductive amination of the reducing keto-disaccharide isomaltulose (Palatinose®) with n-dodecylamine. In the second step the resulting N-dodecylaminopolyols were coupled with allyl glycidyl ether to give polymerizable amphiphilic vinyl saccharides. The copolymerizations with 1-vinyl-2-pyrrolidone were performed as free radical aqueous solution polymerizations. The characterization of the copolymers was carried out by measuring the viscosity and light scattering in water as well as in trichloromethane, in addition to surface tension measurements and solubilization studies. The solution properties of the copolymers in water and trichloromethane differ remarkably. While the values for the intrinsic viscosities in both solvents are comparable, the weight-average molecular weights in water are much higher than those in trichloromethane, indicating the formation of aggregates in aqueous solution. The vinyl pyrrolidone copolymers are also very surface active, lowering the surface tension of water to as low as 30 mN/m. The combination of measurements of surface tensions and solubilization studies indicates that their hydrophobic association behaviour is formally comparable to those of low molecular weight surfactants. Keywords: vinyl saccharides, isomaltulose, hydrophobic association, amphiphilic polymers.

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16

Wong, S. Y. C., I. D. Manger, G. R. Guile, T. W. Rademacher, and R. A. Dwek. "Analysis of carbohydrate-protein interactions with synthetic N-linked neoglycoconjugate probes." Biochemical Journal 296, no. 3 (December 15, 1993): 817–25. http://dx.doi.org/10.1042/bj2960817.

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Recently we have describe a simple efficient chemical method of generating an asparagine side-chain linker with beta-stereochemistry at the anomeric position of neutral oligosaccharides. We now report the 1-N-glycyl beta-derivatization of sialylated saccharides. Several neoglycoconjugates formed using these N-linked inter-mediates were investigated for their usefulness in probing carbohydrate-protein interactions. First, biotinyl derivatives of two xylose/fucose class plant-type oligosaccharides purified from horseradish peroxidase were effective in demonstrating the carbohydrate specificity of polyclonal anti-(horseradish peroxidase) antibodies. Secondly, a fluorescein-labelled asialo- and digalactosylated biantennary complex sugar was synthesized and shown to bind to a Ricinus communis agglutinin column. This galactose-specific recognition was abolished by treating this fluorescein-labelled oligosaccharide with jack bean beta-galactosidase. Finally, two 1-N-glycyl beta-saccharide derivatives were modified with thiophosgene to form their corresponding isothiocyanate derivatives. Coupling of these isothiocyanate derivatives of sugars to BSA, amino-derivatized polystyrene plates and glass-fibre discs resulted in multiple sugar presentation. The binding of an anti-N-acetylglucosamine monoclonal antibody to N,N′-diacetylchitobiose residues presented on BSA and solid supports was shown by e.l.i.s.a. Similarly the binding of concanavalin A to asialo-, agalactosylated biantennary complex oligosaccharide residues attached to BSA was demonstrated by a competitive e.l.i.s.a. Our results demonstrate that N-linked neoglycoconjugates could be made readily available and they are valuable tools for the detailed analyses of carbohydrates and carbohydrate-binding proteins.

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17

INUKAI, Yoshinari, Yasuhiko KAIDA, and Seiji YASUDA. "Adsorption Behavior of Germanium(IV) on Branched-saccharide Chitosan Derivatives." Analytical Sciences 13, Supplement (1997): 221–24. http://dx.doi.org/10.2116/analsci.13.supplement_221.

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18

Maurice, Catherine, Christine Mousty, Bernd Schöllhorn, Bettina Aboab, and Guy Mousset. "Synthesis and electrochemical behaviour of new electroreducible amphiphilic saccharide derivatives." New Journal of Chemistry 22, no. 12 (1998): 1469–77. http://dx.doi.org/10.1039/a804236e.

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19

Yaacoub, Emile-Joseph, Bernhard Skeries, and Klaus Buchholz. "Saccharide polymers, 2. Synthesis and polymerization of exo-glucal derivatives." Macromolecular Chemistry and Physics 198, no. 3 (March 1997): 899–917. http://dx.doi.org/10.1002/macp.1997.021980319.

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20

Staicu, Vasile, Cristina Luntraru, Ioan Calinescu, Ciprian Gabriel Chisega-Negrila, Mircea Vinatoru, Miruna Neagu, Adina Ionuta Gavrila, and Ioana Popa. "Ultrasonic or Microwave Cascade Treatment of Medicinal Plant Waste." Sustainability 13, no. 22 (November 20, 2021): 12849. http://dx.doi.org/10.3390/su132212849.

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In this study, we present a strategy for valorizing lignocellulosic wastes (licorice root and willow bark) that result from industrial extraction of active principles using water as green solvent and aqueous NaOH solution. The wastes were submitted to severe ultrasound (US) and microwave (MW) treatments. The aim of these treatments was to extract the remaining active principles (using water as a solvent) or to prepare them for cellulose enzymatic hydrolysis to hexoses (performed in an NaOH aqueous solution). The content of glycyrrhizic acid and salicin derivatives in licorice root and willow bark wastes, respectively, were determined. The best results for licorice root were achieved by applying the US treatment for 5 min at 25 °C (26.6 mg glycyrrhizic acid/gDM); while, for willow bark, the best results were achieved by applying the MW treatment for 30 min at 120 °C (19.48 mg salicin/gDM). A degradation study of the targeted compounds was also performed and showed good stability of glycyrrhizic acid and salicin derivatives under US and MW treatments. The soluble lignin concentration prior to enzymatic hydrolysis, as well as the saccharide concentration of the hydrolyzed solution, were determined. As compared with the MW treatment, the US treatment resulted in saccharides concentrations that were 5% and 160% higher for licorice root and willow bark, respectively.

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21

Sibrian-Vazquez, Martha, Jorge O. Escobedo, Mark Lowry, and Robert M. Strongin. "Progress toward red and near-infrared (NIR) emitting saccharide sensors." Pure and Applied Chemistry 84, no. 11 (April 30, 2012): 2443–56. http://dx.doi.org/10.1351/pac-con-11-11-06.

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Red-shifted and near-infrared (NIR)-active rhodamine analogs and their boronic acid derivatives were synthesized and studied. These latter compounds function as fluorogenic NIR active substrates for sugar sensing. The effects of benzannulation and boronic acid functionalization on fluorophore optical and sensing properties are described.

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22

Fink, NE, MT Elola, and MO Cabada. "Interaction of ovary lectin with homologous sperm from Bufo arenarum." Reproduction, Fertility and Development 4, no. 5 (1992): 559. http://dx.doi.org/10.1071/rd9920559.

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A soluble beta-galactoside lectin purified from Bufo arenarum ovary agglutinated homologous neuraminidase-treated spermatozoa. Microscopic observations of sperm clusters showed that spermatozoa agglutinated in a random way, but the head-to-head type of sperm agglutination was the most common (94-98%). The lectin activity was specifically inhibited by D-galactose and its derivatives, thio-digalactoside being the most active saccharide inhibitor.

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23

FRISON, Natacha, Philippe MARCEAU, Annie-Claude ROCHE, Michel MONSIGNY, and Roger MAYER. "Oligolysine-based saccharide clusters: synthesis and specificity." Biochemical Journal 368, no. 1 (November 15, 2002): 111–19. http://dx.doi.org/10.1042/bj20020673.

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In search of specific and highly selective sugar clusters for cell receptors, such as membrane lectins, various disaccharides were coupled to small peptide cores through an amide bond. In a first step, the reducing disaccharides, i.e. lactose and three different dimannoses, were converted into glycosyl-pyroglutamyl-β-alanine derivatives. The free carboxylic group of these conjugates was then coupled to the α and ∊ amino groups of the core peptide (Lysn-Ala-Cys-NH2) with n = 1 to 5, with complete substitution leading to homogeneous glycoclusters. The thiol group of the cysteine residue was used to tag the glycosylated oligolysines upon reaction with fluorescein iodoacetamide. The affinity of these glycoclusters towards two plant lectins was assessed by surface plasmon resonance. The selectivity of their cell uptake was investigated by flow cytometry using two types of cells: a human hepatoma cell line (HepG2 cells) expressing the plasma membrane galactose-specific lectin, and monocyte-derived dendritic cells expressing the plasma membrane mannose-specific lectin. The glycoclusters containing four or five disaccharides were shown to bind plant lectins and cell surface membrane lectins with a narrow selectivity and with a high affinity.

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24

Clark, Matthew A., Qunzhao Wang, and Bruce Ganem. "Oxidation of bicyclic oxazolines: applications to glycomimetics and novel saccharide derivatives." Tetrahedron Letters 43, no. 3 (January 2002): 347–49. http://dx.doi.org/10.1016/s0040-4039(01)02161-x.

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25

Ding, Xianglan, Wei Wang, and Fanzuo Kong. "Detritylation of mono- and di-saccharide derivatives using ferric chloride hydrate." Carbohydrate Research 303, no. 4 (October 1997): 445–48. http://dx.doi.org/10.1016/s0008-6215(97)00190-0.

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26

Glümer, Anke, and Emile-Joseph Yaacoub. "Saccharide polymers, 4. Synthesis and polymerisation of 1,2-unsaturated fructopyranoid derivatives." Macromolecular Chemistry and Physics 201, no. 13 (August 1, 2000): 1521–31. http://dx.doi.org/10.1002/1521-3935(20000801)201:13<1521::aid-macp1521>3.0.co;2-6.

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27

Xu, Peng, Xiao-zhuo Chen, Lu Liu, Zhi-ping Jin, and Ping-sheng Lei. "A new series of macrolide derivatives with 4″-O-saccharide substituents." Bioorganic & Medicinal Chemistry Letters 20, no. 18 (September 2010): 5527–31. http://dx.doi.org/10.1016/j.bmcl.2010.07.072.

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28

Ishihara, Masayuki, Shingo Nakamura, Yoko Sato, Tomohiro Takayama, Koichi Fukuda, Masanori Fujita, Kaoru Murakami, and Hidetaka Yokoe. "Heparinoid Complex-Based Heparin-Binding Cytokines and Cell Delivery Carriers." Molecules 24, no. 24 (December 17, 2019): 4630. http://dx.doi.org/10.3390/molecules24244630.

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Heparinoid is the generic term that is used for heparin, heparan sulfate (HS), and heparin-like molecules of animal or plant origin and synthetic derivatives of sulfated polysaccharides. Various biological activities of heparin/HS are attributed to their specific interaction and regulation with various heparin-binding cytokines, antithrombin (AT), and extracellular matrix (ECM) biomolecules. Specific domains with distinct saccharide sequences in heparin/HS mediate these interactions are mediated and require different highly sulfated saccharide sequences with different combinations of sulfated groups. Multivalent and cluster effects of the specific sulfated sequences in heparinoids are also important factors that control their interactions and biological activities. This review provides an overview of heparinoid-based biomaterials that offer novel means of engineering of various heparin-binding cytokine-delivery systems for biomedical applications and it focuses on our original studies on non-anticoagulant heparin-carrying polystyrene (NAC-HCPS) and polyelectrolyte complex-nano/microparticles (N/MPs), in addition to heparin-coating devices.

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29

Ratautaite, Vilma, Raimonda Boguzaite, Migle Beatrice Mickeviciute, Lina Mikoliunaite, Urte Samukaite-Bubniene, Arunas Ramanavicius, and Almira Ramanaviciene. "Evaluation of Electrochromic Properties of Polypyrrole/Poly(Methylene Blue) Layer Doped by Polysaccharides." Sensors 22, no. 1 (December 29, 2021): 232. http://dx.doi.org/10.3390/s22010232.

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Polypyrrole (Ppy) and poly(methylene blue) (PMB) heterostructure (Ppy-PMB) was electrochemically formed on the indium tin oxide (ITO) coated glass slides, which served as working electrodes. For electropolymerization, a solution containing pyrrole, methylene blue, and a saccharide (lactose, sucrose, or heparin) that served as dopant was used. The aim of this study was to compare the effect of the saccharides (lactose, sucrose, and heparin) on the electrochromic properties of the Ppy-PMB layer. AFM and SEM have been used for the analysis of the surface dominant features of the Ppy-PMB layers. From these images, it was concluded that the saccharides used in this study have a moderate effect on the surface morphology. Electrochromic properties were analyzed with respect to the changes of absorbance of the layer at two wavelengths (668 nm and 750 nm) by changing the pH of the surrounding solution and the potential between +0.8 V and −0.8 V. It was demonstrated that the highest absorbance changes are characteristic for all layers in the acidic media. Meanwhile, the absorbance changes of the layers were decreased in the more alkaline media. It was determined that the Ppy-PMB layers with heparin as a dopant were more mechanically stable in comparison to the layers doped with lactose and sucrose. Therefore, the Ppy-PMB layer doped with heparin was selected for the further experiment and it was applied in the design of electrochromic sensors for the determination of three xanthine derivatives: caffeine, theobromine, and theophylline. A linear relationship of ΔA (∆A = A+0.8V − A−0.8V) vs. concentration was determined for all three xanthine derivatives studied. The largest change in optical absorption was observed in the case of theophylline determination.

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Istasse, Thibaut, and Aurore Richel. "Mechanistic aspects of saccharide dehydration to furan derivatives for reaction media design." RSC Advances 10, no. 40 (2020): 23720–42. http://dx.doi.org/10.1039/d0ra03892j.

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The conversion of abundant hexoses and pentoses to 5-hydroxymethylfurfural (5-HMF) and 2-furfural (2-F) is subject to intensive research in the hope of achieving competitive production of diverse materials from renewable resources.

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KAIDA, Yasuhiko. "Adsorption Behavior of Semi-Metal Ions on Branched-Saccharide-Polyaglylamine (PAA) Derivatives." Kobunshi 49, no. 12 (2000): 841. http://dx.doi.org/10.1295/kobunshi.49.841.

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32

Yim, Jin-Heong, Hyun-Dam Jeong, and Lyong Sun Pu. "The preparation of nanoporous siloxane films using saccharide derivatives as new porogen." Thin Solid Films 476, no. 1 (April 2005): 46–50. http://dx.doi.org/10.1016/j.tsf.2004.09.005.

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33

Ho, S. C., J. L. Wang, and M. Schindler. "Carbohydrate binding activities of Bradyrhizobium japonicum. I. Saccharide-specific inhibition of homotypic and heterotypic adhesion." Journal of Cell Biology 111, no. 4 (October 1, 1990): 1631–38. http://dx.doi.org/10.1083/jcb.111.4.1631.

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Bradyrhizobium japonicum (R110d) exhibited four saccharide-specific binding activities: (a) adsorption to Sepharose beads containing covalently coupled lactose; (b) homotypic agglutination through one pole of the cell (star formation); (c) heterotypic adhesion to the cultured soybean cell line, SB-1; and (d) attachment to roots of soybean plants. Each of these binding activities can be inhibited by the addition of galactose or lactose, but not by derivatives such as N-acetyl-D-galactosamine or melibiose. Treatment of wild-type bacteria with N-methyl-N'-nitro-N-nitrosoguanidine followed by selection on the basis of reduced binding to SB-1 cells, resulted in two specific mutants, designated N4 and N6. Compared to wild type, these two mutants also exhibited decreased binding activity in: (a) adsorption to lactose-Sepharose beads; (b) homotypic star formation; and (c) heterotypic attachment to roots of soybeans plants. These results suggest that all four of the saccharide-inhibitable binding activities of Bradyrhizobium japonicum may be mediated by the same mechanism(s) or molecular component(s).

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34

Xiang, Nan, Hui Xie, Liuwei Qin, Min Wang, Xinbo Guo, and Wen Zhang. "Effect of Climate on Volatile Metabolism in ‘Red Globe’ Grapes (Vitis vinifera L.) during Fruit Development." Foods 11, no. 10 (May 16, 2022): 1435. http://dx.doi.org/10.3390/foods11101435.

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With unique flavor and nutritional value, grapes are popular for eating and for the byproducts obtained in their processing. This study cultivated a popular grape variety, ‘Red Globe’, in two regions with different climates to investigate the discrepancies in their volatiles in response to climate. Saccharides, organic acids and transcriptomic and volatile metabolic analyses were studied separately via GC-FID, RNA sequencing and GC-MS/MS methods during the development of grape berries. In total, 83 volatiles were determined in samples, with (E)-2-hexenal the most abundant. Fatty acid derivatives and terpenoids in grapes showed discrepancies in different climates, and some of them were correlated to specific transcription factors. VvWRKY22 was influenced by climate conditions and was relative to saccharide accumulation. MYB-related transcription factors (TFs) were highly correlated with volatiles that accumulated during fruit ripening, especially decanal. Terpenoids showed correlations with a gene module that contained ERFs and HSFs. The findings support the hypothesis that fruit maturity and volatile formations vary in grape berries under different climates. Moreover, specific TFs could participate in volatile accumulations. The given results not only serve to enrich theoretical knowledge on the regulatory mechanism of volatiles in grapes, but also provide guidance for enhancing grape flavor and aroma by modulating cultivational conditions.

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Maurice, Catherine, Bernd Schöllhorn, Bettina Aboab, Guy Mousset, and Christine Mousty. "Electrochemical behaviour of new electroreducible amphiphilic saccharide derivatives II: Electroreduction in protic media." New Journal of Chemistry 23, no. 12 (1999): 1171–75. http://dx.doi.org/10.1039/a906282c.

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36

Clark, Matthew A., Qunzhao Wang, and Bruce Ganem. "ChemInform Abstract: Oxidation of Bicyclic Oxazolines: Applications to Glycomimetics and Novel Saccharide Derivatives." ChemInform 33, no. 15 (May 22, 2010): no. http://dx.doi.org/10.1002/chin.200215132.

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37

Thornalley, P. J. "The enzymatic defence against glycation in health, disease and therapeutics: a symposium to examine the concept." Biochemical Society Transactions 31, no. 6 (December 1, 2003): 1341–42. http://dx.doi.org/10.1042/bst0311341.

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Glycation of proteins, nucleotides and basic phospholipids by glucose, glyoxal, methylglyoxal, 3-deoxyglucosone and other saccharide derivatives is potentially damaging to the proteome and mutagenic. It is now recognized that there is an enzymatic defence against glycation – a group of enzymes that suppress the physiological levels of potent glycating agents and repair glycated proteins: glyoxalase I, aldehyde reductases and dehydrogenases, amadoriase and fructosamine 3-phosphokinase. The enzymatic defence against glycation influences morbidity and the efficiency of drug therapy in certain diseases. Improved understanding of the balance between glycation and the enzymatic anti-glycation defence will advance disease diagnosis and therapy.

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38

Quan, Jing, Yan Zheng, Bo Jiang, Limin Zhu, and Xianfu Lin. "Improving solubility of lipophilic drugs: Enzymatic synthesis of drug-saccharide derivatives in nonaqueous media." Journal of Biotechnology 136 (October 2008): S514. http://dx.doi.org/10.1016/j.jbiotec.2008.07.644.

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39

SARBAJNA, S., and N. ROY. "ChemInform Abstract: Synthesis of Tri- and Tetra-saccharide Derivatives Related to Klebsiella Type 57." ChemInform 29, no. 37 (June 19, 2010): no. http://dx.doi.org/10.1002/chin.199837237.

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40

NTARIMA, Patricia, Wim NERINCKX, Klaus KLARSKOV, Bart DEVREESE, Mahalingeshwara K. BHAT, Jozef VAN BEEUMEN, and Marc CLAEYSSENS. "Epoxyalkyl glycosides of d-xylose and xylo-oligosaccharides are active-site markers of xylanases from glycoside hydrolase family 11, not from family 10." Biochemical Journal 347, no. 3 (April 25, 2000): 865–73. http://dx.doi.org/10.1042/bj3470865.

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A series of Ω-epoxyalkyl glycosides of D-xylopyranose, xylobiose and xylotriose were tested as potential active-site-directed inhibitors of xylanases from glycoside hydrolase families 10 and 11. Whereas family-10 enzymes (Thermoascus aurantiacus Xyn and Clostridium thermocellum Xyn Z) are resistant to electrophilic attack of active-site carboxyl residues, glycoside hydrolases of family 11 (Thermomyces lanuginosus Xyn and Trichoderma reesei Xyn II) are irreversibly inhibited. The apparent inactivation and association constants (ki, 1/Ki) are one order of magnitude higher for the xylobiose and xylotriose derivatives. The effects of the aglycone chain length can clearly be described. Xylobiose and n-alkyl β-D-xylopyranosides are competitive ligands and provide protection against inactivation. MS measurements showed 1:1 stoichiometries in most labelling experiments. Electrospray ionization MS/MS analysis revealed the nucleophile Glu86 as the modified residue in the T. lanuginosus xylanase when 2,3-epoxypropyl β-D-xylopyranoside was used, whereas the acid/base catalyst Glu178 was modified by the 3,4-epoxybutyl derivative. The active-site residues Glu86 and Glu177 in T. reesei Xyn II are similarly modified, confirming earlier X-ray crystallographic data [Havukainen, Törrönen, Laitinen and Rouvinen (1996) Biochemistry 35, 9617-9624]. The inability of the Ω-epoxyalkyl xylo(oligo)saccharide derivatives to inactivate family-10 enzymes is discussed in terms of different ligand-subsite interactions.

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41

Demeter, Fruzsina, Patrik Török, Alexandra Kiss, Richárd Kovásznai-Oláh, Zsuzsa Máthéné Szigeti, Viktória Baksa, Fruzsina Kovács, et al. "First Synthesis of DBU-Conjugated Cationic Carbohydrate Derivatives and Investigation of Their Antibacterial and Antifungal Activity." International Journal of Molecular Sciences 24, no. 4 (February 10, 2023): 3550. http://dx.doi.org/10.3390/ijms24043550.

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The emergence of drug-resistant bacteria and fungi represents a serious health problem worldwide. It has long been known that cationic compounds can inhibit the growth of bacteria and fungi by disrupting the cell membrane. The advantage of using such cationic compounds is that the microorganisms would not become resistant to cationic agents, since this type of adaptation would mean significantly altering the structure of their cell walls. We designed novel, DBU (1,8-diazabicyclo[5.4.0]undec-7-ene)-derived amidinium salts of carbohydrates, which may be suitable for disturbing the cell walls of bacteria and fungi due to their quaternary ammonium moiety. A series of saccharide-DBU conjugates were prepared from 6-iodo derivatives of d-glucose, d-mannose, d-altrose and d-allose by nucleophilic substitution reactions. We optimized the synthesis of a d-glucose derivative, and studied the protecting group free synthesis of the glucose-DBU conjugates. The effect of the obtained quaternary amidinium salts against Escherichia coli and Staphylococcus aureus bacterial strains and Candida albicans yeast was investigated, and the impact of the used protecting groups and the sugar configuration on the antimicrobial activity was analyzed. Some of the novel sugar quaternary ammonium compounds with lipophilic aromatic groups (benzyl and 2-napthylmethyl) showed particularly good antifungal and antibacterial activity.

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42

Chen, Jiangang, Wenfang Lu, Hao Chen, Xiaoli Bian, and Guangde Yang. "A New Series of Salicylic Acid Derivatives as Non-saccharide α-Glucosidase Inhibitors and Antioxidants." Biological and Pharmaceutical Bulletin 42, no. 2 (February 1, 2019): 231–46. http://dx.doi.org/10.1248/bpb.b18-00661.

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43

Meng, Junxiu, Shaoqing Yu, Shengbiao Wan, Sumei Ren, and Tao Jiang. "Synthesis, Saccharide-Binding and Anti-cancer Cell Proliferation Properties of Arylboronic Acid Derivatives of Indoquinolines." Chemical Biology & Drug Design 78, no. 5 (September 15, 2011): 816–25. http://dx.doi.org/10.1111/j.1747-0285.2011.01196.x.

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44

Newman, Janet, Karine Caron, Tom Nebl, and Thomas S. Peat. "Structures of the transcriptional regulator BgaR, a lactose sensor." Acta Crystallographica Section D Structural Biology 75, no. 7 (June 26, 2019): 639–46. http://dx.doi.org/10.1107/s2059798319008131.

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The structure of BgaR, a transcriptional regulator of the lactose operon inClostridium perfringens, has been solved by SAD phasing using a mercury derivative. BgaR is an exquisite sensor of lactose, with a binding affinity in the low-micromolar range. This sensor and regulator has been captured bound to lactose and to lactulose as well as in a nominal apo form, and was compared with AraC, another saccharide-binding transcriptional regulator. It is shown that the saccharides bind in the N-terminal region of a jelly-roll fold, but that part of the saccharide is exposed to bulk solvent. This differs from the classical AraC saccharide-binding site, which is mostly sequestered from the bulk solvent. The structures of BgaR bound to lactose and to lactulose highlight how specific and nonspecific interactions lead to a higher binding affinity of BgaR for lactose compared with lactulose. Moreover, solving multiple structures of BgaR in different space groups, both bound to saccharides and unbound, verified that the dimer interface along a C-terminal helix is similar to the dimer interface observed in AraC.

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45

WANG, RONG-MIN, FANG-YING LI, XIAO-JIE WANG, QUAN-FANG LI, YU-FENG HE, and YAN-BING WANG. "THE APPLICATION OF FEATHER KERATIN AND ITS DERIVATIVES IN TREATMENT OF POTATO STARCH WASTEWATER." Functional Materials Letters 03, no. 03 (September 2010): 213–16. http://dx.doi.org/10.1142/s1793604710001275.

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In this paper, stable and homogeneous feather keratin was effectively extracted from feathers. Its molecular weight is 20kDa with low dispersivity. The extracted feather keratin (FK) and its derivatives (FK-ET) were used as natural polymer flocculants. It was a new kind of effective and innoxious flocculant for the COD removal of potato starch wastewater. The removal rate of COD was up to 75% under the following optimal condition: 100mL of initial wastewater (COD = 7380), T = 20°C, [FK-ET] = 0.4g/L, [Bent] = 4g/L, pH = 8.0. Compared with traditional flocculants, keratin flocculants are innoxious natural polymers. Their sludge is easy to be treated, and there is no further pollution. Also, the flocculating constituents, which containing keratin, starch, saccharide, protein and other solubility substances from wastewaters, should be reutilized. It has practical application value in water treatment as a kind of natural polymer flocculant.

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46

Daghildjian, Katia, Athena Kasselouri, Marline N’Diaye, Jean-Philippe Michel, Juliette Vergnaud, Florent Poyer, Philippe Maillard, and Véronique Rosilio. "Mannose distribution in glycoconjugated tetraphenylporphyrins governs their uptake mechanism and phototoxicity." Journal of Porphyrins and Phthalocyanines 23, no. 01n02 (January 2019): 175–84. http://dx.doi.org/10.1142/s1088424619500184.

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Tetraphenylporphyrins (TPPs) have been proposed for the treatment of retinoblastoma by photodynamic therapy. Glycoconjugated compounds were synthesized for improving TPP solubility and amphipathy, and to specifically target mannose receptors overexpressed at the surface of cells. The efficiency of four TPP derivatives with different chemical structures was compared by phototoxicity tests and flow cytometry experiments. Interestingly, the absence/presence and distribution of saccharide moieties in the various compounds affected differently their mechanism of interaction with cancer cells and their phototoxic efficiency. For glycodendrimeric TPP-1 and TPP-2 incubated with retinoblastoma cells, a fast two-step uptake-equilibrium process was observed, whereas for a dendrimeric TPP without saccharide moieties (TPP-1c) and a glycoconjugated compound with no dendrimeric structure (TPP(DegMan)[Formula: see text] uptake was very slow. The difference in uptake profiles and kinetics between TPP-1c on the one hand and TPP-1 and TPP-2 on the other hand would account for the interaction of the two glycodendrimeric compounds with a mannose receptor. These TPPs encapsulated in endosomes would induce less damage to cells upon illumination. TPP(DegMan)[Formula: see text] showed the highest phototoxicity, but its efficiency was unaffected by pretreatment of cells by mannan. The penetration of this glycoconjugated compound in cells and its phototoxic effect appeared independent of its interaction with a mannose receptor. Thus, if glycoconjugation influenced TPPs behavior in solution and interaction with serum proteins, phototoxicity was not necessarily related to upfront molecular recognition.

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47

Cumpstey, Ian. "Chemical Modification of Polysaccharides." ISRN Organic Chemistry 2013 (September 10, 2013): 1–27. http://dx.doi.org/10.1155/2013/417672.

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This review covers methods for modifying the structures of polysaccharides. The introduction of hydrophobic, acidic, basic, or other functionality into polysaccharide structures can alter the properties of materials based on these substances. The development of chemical methods to achieve this aim is an ongoing area of research that is expected to become more important as the emphasis on using renewable starting materials and sustainable processes increases in the future. The methods covered in this review include ester and ether formation using saccharide oxygen nucleophiles, including enzymatic reactions and aspects of regioselectivity; the introduction of heteroatomic nucleophiles into polysaccharide chains; the oxidation of polysaccharides, including oxidative glycol cleavage, chemical oxidation of primary alcohols to carboxylic acids, and enzymatic oxidation of primary alcohols to aldehydes; reactions of uronic-acid-based polysaccharides; nucleophilic reactions of the amines of chitosan; and the formation of unsaturated polysaccharide derivatives.

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Luboradzki, Roman, and Zbigniew Pakulski. "Novel class of saccharide-based organogelators: glucofuranose derivatives as one of the smallest and highly efficient gelators." Tetrahedron 60, no. 21 (May 2004): 4613–16. http://dx.doi.org/10.1016/j.tet.2004.03.074.

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49

Luo, Yan, Zhenjun Zhao, Hujiang Chen, Xueli Pan, Risheng Li, Dewen Wu, Xianchun Hu, Lingling Zhang, Huawei Wu, and Xinghui Li. "Dynamic Analysis of Physicochemical Properties and Polysaccharide Composition during the Pile-Fermentation of Post-Fermented Tea." Foods 11, no. 21 (October 26, 2022): 3376. http://dx.doi.org/10.3390/foods11213376.

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Ultra-high performance liquid chromatography-quadrupole-time of flight tandem mass spectrometry (UHPLC-Q-TOF-MS/MS) was used to study the diversity of tea polysaccharides and the dynamic changes in the physicochemical indexes of tea samples. FT-IR spectra and the free radical scavenging ability of tea polysaccharides, during pile-fermentation of post-fermented tea, were analyzed. The results showed that 23 saccharide components in tea polysaccharides were identified: these belonged to 11 monosaccharides, 5 oligosaccharides, and 6 derivatives of monosaccharides and oligosaccharides. The abundance of oligosaccharides decreased gradually, while monosaccharides, and derivatives of monosaccharides and oligosaccharides increased gradually with the development of pile-fermentation. According to the differences in polysaccharide composition and their abundance, the tea polysaccharide samples extracted from different pile-fermentation stages could be clearly classed into three groups, W-0, W-1~W-4 and W-5~C-1. The pile-fermentation process affected the yield, the content of each component, FT-IR spectra, and the DPPH free radical scavenging ability of tea polysaccharides. Correlation analysis showed that microorganisms were directly related to the changes in composition and the abundance of polysaccharides extracted from different pile-fermentation stages. The study will further help to reveal the function of tea polysaccharides and promote their practical application as a functional food.

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Kaur, Kamaljeet, Sonika Arti, Tushar K. Ghosh, Tarlok S. Banipal, and Parampaul K. Banipal. "To study the interactions between saccharide/their derivatives and bactericidal cefadroxil drug: Volumetric, acoustic and molecular docking studies." Journal of Chemical Thermodynamics 159 (August 2021): 106477. http://dx.doi.org/10.1016/j.jct.2021.106477.

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