10,440 results match your criteria Carbohydrate research[Journal]


Simple and environmentally friendly preparation of cellulose hydrogels using an ionic liquid.

Carbohydr Res 2020 Jun 7;494:108054. Epub 2020 Jun 7.

Graduate School of Environmental Engineering for Symbiosis, Soka University, 1-236 Tangi-cho, Hachioji, Tokyo, 192-8577, Japan. Electronic address:

In this study, we developed an easy process for the production of cellulose hydrogels over a wide concentration range by using an ionic liquid/DMSO mixed solution that can easily be recycled at room temperature and has low environmental impact. Cellulose was completely dissolved at 6 to 20 wt% with respect to the [BMIm][OAc]/DMSO mixed solution at room temperature and ambient pressure. Placing the cellulose solution in a mold and immersing it in deionized water caused solvent replacement of the [BMIm][OAc]/DMSO mixed solution with deionized water, making it easy to obtain a cellulose hydrogel without using a crosslinking agent. Read More

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http://dx.doi.org/10.1016/j.carres.2020.108054DOI Listing

A detailed in silico analysis of the amylolytic family GH126 and its possible relatedness to family GH76.

Carbohydr Res 2020 Jun 23;494:108082. Epub 2020 Jun 23.

Laboratory of Protein Evolution, Institute of Molecular Biology, Slovak Academy of Sciences, SK-84551, Bratislava, Slovakia; Department of Biology, Faculty of Natural Sciences, University of SS. Cyril and Methodius, SK-91701, Trnava, Slovakia. Electronic address:

The glycoside hydrolase (GH) family 126 was established based on the X-ray structure determination of the amylolytic enzyme CPF_2247 from Clostridium perfringens genome. Its original identification as a putative carbohydrate-active enzyme was based on its low, yet significant sequence identity to members of the family GH8, which are inverting endo-β-1,4-glucanases. As the family GH8 forms the clan GH-M with GH48, the CPF_2247 protein also exhibits similarities with members of the family GH48. Read More

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http://dx.doi.org/10.1016/j.carres.2020.108082DOI Listing

First-line anti-tubercutilosis drugs-loaded starch nanocrystals for combating the threat of M. tuberculosis H37Rv strain.

Carbohydr Res 2020 Jun 27;495:108070. Epub 2020 Jun 27.

School of Chemical Sciences, Central University of Gujarat, Gandhinagar, 382030, India. Electronic address:

Nanoparticles-based drug delivery is at the forefront in the field of pharmaceutical and medicinal research to eradicate or alleviate the associated impediments, such as prolonged treatment time, high doses, toxicity and resistance problem of anti-tuberculosis drugs for the treatment of age-old tuberculosis disease. Herein, the first-line anti-tuberculosis drugs were loaded into the biodegradable starch nanocrystals and native starch to improve the therapeutic profile addressing the existing issues related to conventional drugs. The loading performance of anti-tuberculosis drugs with starch nanocrystals and native starch was found in the range of 65-95%. Read More

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http://dx.doi.org/10.1016/j.carres.2020.108070DOI Listing

Synthesis of C6-substituted UDP-GlcNAc derivatives.

Carbohydr Res 2020 Jun 26;495:108071. Epub 2020 Jun 26.

Department of Chemistry, University of Toronto, 80 St. George Street, Toronto, Ontario, M5S 3H6, Canada. Electronic address:

UDP-sugar analogs are useful for the study of glycosyltransferases and the production of unnatural glycans. The preparation of five UDP-GlcNAc derivatives is reported with 6-deoxy, 6-azido, 6-amino, 6-mercapto, or 6-fluoro substitutions. A concise chemoenzymatic synthesis was developed using the kinase NahK (B. Read More

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http://dx.doi.org/10.1016/j.carres.2020.108071DOI Listing

Optimization of amylomaltase for the synthesis of α-arbutin derivatives as tyrosinase inhibitors.

Carbohydr Res 2020 Jun 21;494:108078. Epub 2020 Jun 21.

Division of Biochemistry, Department of Pre-Clinical Science, Faculty of Medicine, Thammasat University, Pathumthani, 12120, Thailand. Electronic address:

α-Arbutin is widely used as a skin-whitening agent in the pharmaceutical and cosmetic industries because of its inhibitory effect on tyrosinase, an important enzyme for generating melanin pigments. Given the increasing demand for such products, we synthesized α- and β-arbutin-α-D-glycosides through transglycosylation reactions catalyzed by a recombinant amylomaltase, using tapioca starch and α- and β-arbutin as donor and acceptor molecules, respectively. The catalytic yield of products by the amylomaltase was greater with α-arbutin than with β-arbutin. Read More

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http://dx.doi.org/10.1016/j.carres.2020.108078DOI Listing

Extraction methods, chemical characterizations and biological activities of mushroom polysaccharides: A mini-review.

Carbohydr Res 2020 Jun 18;494:108037. Epub 2020 Jun 18.

College of Food and Biological Engineering, Shaanxi University of Science and Technology, Xi'an, 710021, China. Electronic address:

Edible mushrooms are an important constituents of our daily diet due to their rich nutrition and beneficial properties for human health. Polysaccharides, the main component of edible mushrooms, attracted more and more attention because of their complex structure and diverse biological activities. Edible mushroom polysaccharides contain diverse medical activities, including anti-tumor, anti-inflammatory, antibacterial, hypoglycemic, and immune-enhancing activities et al. Read More

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http://dx.doi.org/10.1016/j.carres.2020.108037DOI Listing

Nano-sized biopolymer levan: Its antimicrobial, anti-biofilm and anti-cancer effects.

Carbohydr Res 2020 Jun 9;494:108068. Epub 2020 Jun 9.

Hacettepe University, Faculty of Science, Department of Biology, Ankara, Turkey. Electronic address:

Among other polysaccharides, levan is a fructan with great potential in biotechnological applications due to its functional properties. The levan has only been available in small quantities because of its high cost. Here, a levan-producing microorganism was isolated from soil and identified as Pseudomonas mandelii. Read More

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http://dx.doi.org/10.1016/j.carres.2020.108068DOI Listing

Two new phenylethanoid glycosides from Ginkgo biloba leaves and their tyrosinase inhibitory activities.

Carbohydr Res 2020 Jun 16;494:108059. Epub 2020 Jun 16.

School of Chemistry and Chemical Engineering, Xuchang University, Xuchang, China. Electronic address:

Two undescribed phenylethanoid glycosides, Ginkgoside C (1) and D (2), together with ten known glycosides (3-12) were isolated from Ginkgo biloba leaves. Their structures were characterized by physical data analyses such as NMR, HRESIMS, as well as chemical hydrolysis. All compounds were tested for their tyrosinase inhibitory activities. Read More

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http://dx.doi.org/10.1016/j.carres.2020.108059DOI Listing

Structure of the O-specific polysaccharide from Azospirillum formosense CC-Nfb-7(T).

Carbohydr Res 2020 Jun 10;494:108060. Epub 2020 Jun 10.

Institute of Biochemistry and Physiology of Plants and Microorganisms, Russian Academy of Sciences, 13 Prospekt Entuziastov, Saratov, 410049, Russia; Saratov State University, 83 Ulitsa Astrakhanskaya, Saratov, 410012, Russia.

The lipopolysaccharide was obtained from the cells of Azospirillum formosense CC-Nfb-7(T), a diazotrophic bacterium isolated from agricultural soil. The O-specific polysaccharide (OPS) was released by mild acid hydrolysis of the lipopolysaccharide and was studied by sugar analysis along with H and C NMR spectroscopy, including H,H COSY, TOCSY, ROESY, H,C HSQC, and HMBC experiments, and Smith degradation. The following structure of partially methylated OPS composed of trisaccharide repeating units was established. Read More

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http://dx.doi.org/10.1016/j.carres.2020.108060DOI Listing

Synthesis of new curcumin derivatives as influential antidiabetic α-glucosidase and α-amylase inhibitors with anti-oxidant activity.

Carbohydr Res 2020 Jun 10;494:108069. Epub 2020 Jun 10.

Department of Chemistry, College of Sciences, Shiraz University, Shiraz, Iran.

In this study, a new class of curcumin derivatives was synthesized using a multicomponent reaction containing curcumin, aldehydes, and malononitrile. This new protocol afforded a novel class of 4H-pyran heterocycles incorporating curcumin moiety. The products were obtained in the presence of p-toluenesulfonic acid (PTSA) as a catalyst in ethanol solvent in good to excellent yields. Read More

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http://dx.doi.org/10.1016/j.carres.2020.108069DOI Listing

Efficient synthesis of α(1,2)-linked oligomannoside derivatives through one-pot glycosylation.

Carbohydr Res 2020 Jun 11;494:108072. Epub 2020 Jun 11.

Graduate School of Science and Technology, Gunma University, 1-5-1, Tenjin-cho, Kiryu, Gunma, 376-8515, Japan. Electronic address:

An α(1,2)-linked oligomannoside derivative having a free C-2 hydroxyl group and a C-3 pivaloyl group was synthesized from a thiophenyl mannose derivative 1 using a one-pot self-condensation and applying a α-stereoselective procedure. The mannosylation exclusively generated α-mannoside linkages. The observed α-directing effect was rationalized by the remote participation of the pivaloyl group in C-3 position. Read More

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http://dx.doi.org/10.1016/j.carres.2020.108072DOI Listing

Preparation of alginate oligosaccharides and their biological activities in plants: A review.

Carbohydr Res 2020 Jun 7;494:108056. Epub 2020 Jun 7.

Dalian Engineering Research Center for Carbohydrate Agricultural Preparations, Liaoning Provincial Key Laboratory of Carbohydrates, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian, 116023, China. Electronic address:

Alginate oligosaccharide (AOS) is the degradation product of alginates extracted from brown algae. As a multifunctional oligomer, it has attracted widespread attention in plant research. Different methods of preparation generate AOS possessing diverse structural properties, and result in differences in AOS activity. Read More

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http://dx.doi.org/10.1016/j.carres.2020.108056DOI Listing

Copper mediated A-coupling reaction for the preparation of enantioselective deoxy sugar based chiral propargylamines using bifunctional ligand l-proline.

Carbohydr Res 2020 Jun 1;494:108053. Epub 2020 Jun 1.

Department of Chemistry, University of Lucknow, Lucknow, 226007, India. Electronic address:

An efficient three component coupling of aromatic aldehyde, deoxy sugar based alkyne (α-2-deoxy propargyl glycoside) and heterocyclic amine have been refluxed to synthesize stereoselective chiral propargylamines with good to excellent yield using only CuI catalyst along with bifunctional ligand l-proline. This method has proved to be applicable in wide range of substrates and found highly enantioselective with respect to earlier reported methods. In addition, l-proline was found as a chiral source which demonstrated that it could be developed as a highly enantioselective method for the construction of deoxy sugar based chiral propargylamines. Read More

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http://dx.doi.org/10.1016/j.carres.2020.108053DOI Listing

Arctium lappa L. polysaccharide can regulate lipid metabolism in type 2 diabetic rats through the SREBP-1/SCD-1 axis.

Carbohydr Res 2020 Jun 7;494:108055. Epub 2020 Jun 7.

National Resources Center of Chinese Material Medica, China Academy of Chinese Medical Sciences, Beijing, China.

In the analysis of risk factors of diabetes mellitus with coronary heart disease, dyslipidemia is the most important. Previous studies have found that Arctium lappa L. polysaccharide (ALP) can regulate lipid metabolism in type 1 diabetic rats, but it has not been studied in type 2 diabetes. Read More

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http://dx.doi.org/10.1016/j.carres.2020.108055DOI Listing

Generation of a glycosylated asparagine residue through chemoselective acylation of a glycosylhydrazide.

Carbohydr Res 2020 Jul 4;493:108022. Epub 2020 May 4.

Department of Chemistry, Seattle University, Seattle, WA, 98122, USA. Electronic address:

Herein, we report the first selective anomeric N-acylation of a glycosylhydrazide. We show that this transformation can be harnessed to generate amino acid building blocks including FmocAsn(GlcNAc)OH (1), a residue that has been previously shown to be a competent reagent in the solid-phase peptide synthesis of N-linked glycopeptides. Read More

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http://dx.doi.org/10.1016/j.carres.2020.108022DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC7325706PMC

Greener approach for synthesis of N,N,N-trimethyl chitosan (TMC) using ternary deep eutectic solvents (TDESs).

Carbohydr Res 2020 Jul 15;493:108033. Epub 2020 May 15.

Department of Chemical Engineering, Institute of Chemical Technology, Nathalal Parekh Marg, Matunga, Mumbai, 400 019, India. Electronic address:

N,N,N-trimethyl chitosan (TMC), quaternized hydrophilic derivative of chitosan, has been projected to have wide applications in the pharmaceutical industry owing to its improved solubility at physiological conditions. However, the conventional synthesis of TMC involves toxic organic agents, which complicates its use for biological applications. Moreover, these reactions result into unwanted O-methylation and scission of the parent polymer. Read More

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http://dx.doi.org/10.1016/j.carres.2020.108033DOI Listing

Structure of the O-specific polysaccharide of Aeromonas veronii bv. sobria strain Pt393 isolated from rainbow trout (Oncorhynchus mykiss), which contains a rarely occurring sugar 4-acetamido-4,6-dideoxy-d-galactose, tomosamine.

Carbohydr Res 2020 Jul 21;493:108036. Epub 2020 May 21.

Department of Genetics and Microbiology, M. Curie-Sklodowska University, Akademicka 19, 20-033, Lublin, Poland. Electronic address:

The O-specific polysaccharide (OPS) was isolated from the lipopolysaccharide of Aeromonas veronii bv. sobria strain Pt393, which is pathogenic to the rainbow trout (Oncorhynchus mykiss), after mild acid hydrolysis followed by GPC. The high-molecular-weight OPS fraction was studied with chemical methods, mass spectrometry, and H and C NMR spectroscopy techniques, including 2D H,H COSY, TOCSY, NOESY, H-detected heteronuclear H,C HSQC, and HMBC experiments. Read More

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http://dx.doi.org/10.1016/j.carres.2020.108036DOI Listing

Chemical and physical properties of nanocrystalline chitosan by the method: Modified nanochitosan complex and process of obtaining modified nanochitosan.

Carbohydr Res 2020 Jul 21;493:108035. Epub 2020 May 21.

Laboratory of Biomaterials, Materials Engineering Department, Federal University of Rio Grande Do Sul - UFRGS, Porto Alegre, RS, Brazil.

Nanocrystalline chitosan (NCC) is a modified form of chitosan, prepared from the method for obtaining chitosan acetate (CA). Due to the greater crystallinity of chitosan nanoparticles in relation to CA, NCC is more thermally stable and thus has great potential in the development of a new generation of biomaterials potentially useful in regenerative medicine and tissue engineering. NCC is also characterized by having similar properties to its precursor chitosan, such as its biocompatibility, bioactivity, ability to be bioabsorbed and lack of toxicity. Read More

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http://dx.doi.org/10.1016/j.carres.2020.108035DOI Listing

Identification of low molecular weight degradation products from chitin and chitosan by electrospray ionization time-of-flight mass spectrometry.

Carbohydr Res 2020 Jul 25;493:108046. Epub 2020 May 25.

Department of Chemistry, Colorado State University, 1801 Campus Delivery, Fort Collins, CO, 80523, United States; Department of Chemical and Biological Engineering, Colorado State University, 1370 Campus Delivery, Fort Collins, CO, 80523, United States; School of Biomedical Engineering, Colorado State University, 1376 Campus Delivery, Fort Collins, CO, 80523, United States. Electronic address:

The beneficial effects provided by chitosan oligosaccharides (COS) make them of interest in medical research. The monomers that constitute COS confer distinct properties, so controlling COS composition during their production is significant. In this work, we degraded chitin and chitosan polymers and identified low molecular weight products such as COS that formed, using electrospray ionization time-of-flight mass spectrometry. Read More

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http://dx.doi.org/10.1016/j.carres.2020.108046DOI Listing

Synthesis of 2'-paclitaxel 2-deoxy-2-fluoro-glucopyranosyl carbonate for specific targeted delivery to cancer cells.

Carbohydr Res 2020 Jul 25;493:108034. Epub 2020 May 25.

Department of Pharmacy, Qilu Hospital of Shandong University, Jinan, 250012, Shandong Province, PR China.

A novel 2-fluorodeoxyglucose conjugated derivative of paclitaxel was efficiently synthesized using a linker between 2'-OH of paclitaxel and C1-hydroxyl group of 2-fluorodeoxyglucose. In preparation of the prodrug, allyl carbonates were selected as the protective group and the efficient one-step removal of allyloxycarbonyl groups at the end of the synthesis using palladium chemistry gave the target molecule in good yield. The prodrug not only improved the pharmaceutical properties of paclitaxel, such as solubility and stability, but also demonstrated enhanced cytotoxicity and selectivity for cancer cells and less toxicity toward normal HUVEC cells. Read More

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http://dx.doi.org/10.1016/j.carres.2020.108034DOI Listing
July 2020
1.929 Impact Factor

Production of tagatose and talose through isomerization of galactose in a buffer solution under subcritical water conditions.

Carbohydr Res 2020 Jul 11;493:108031. Epub 2020 May 11.

Division of Food Science and Biotechnology, Graduate School of Agriculture, Kyoto University, Sakyo-ku, Kyoto, 606-8502, Japan. Electronic address:

Galactose was isomerized in pure water or in 10 mmol/L sodium phosphate buffer at 160 °C under pressurized conditions. The isomerization of galactose to tagatose and talose in phosphate buffer resulted in 14% and 1.4% yields, respectively, which were significantly higher than those obtained in subcritical pure water (0. Read More

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http://dx.doi.org/10.1016/j.carres.2020.108031DOI Listing

Synthesis and mannosidase inhibitory profile of a small library of aminocyclitols from shikimic acid-derived scaffolds.

Carbohydr Res 2020 Jul 11;493:108027. Epub 2020 May 11.

Department of Glycobiology, Institute of Chemistry, Centre for Glycomics, Slovak Academy of Sciences, Dúbravská Cesta 9, 845 38, Bratislava, Slovak Republic.

A short synthetic route to a small library of aminocyclitols 14·HCl-19·HCl has been elaborated from the common shikimic acid-derived scaffolds 20 and 21. The developed strategy features three oxidative processes ‒ ozonolysis, dihydroxylation and epoxidation ‒ as the key transformations. The stereochemistry of the newly created stereocentres was confirmed either via crystallographic analysis or by means of NOESY experiments conducted on advanced intermediates. Read More

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http://dx.doi.org/10.1016/j.carres.2020.108027DOI Listing

Enzymatic transfucosylation for synthesis of human milk oligosaccharides.

Carbohydr Res 2020 Jul 8;493:108029. Epub 2020 May 8.

Protein Chemistry and Enzyme Technology, Department of Biotechnology and Biomedicine, Technical University of Denmark, Søltofts Plads 221, 2800 Kgs, Lyngby, Denmark. Electronic address:

Human milk oligosaccharides (HMOs) are a family of structurally distinct carbohydrate oligomers present in human milk. HMOs protect breastfed babies against infection and promote the development of infant health and cognition. In the gut, fucosylated HMOs in particular function as decoy receptors that intercept epithelial attachment of enteric pathogens and hence help reduce infection. Read More

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http://dx.doi.org/10.1016/j.carres.2020.108029DOI Listing

Conformation, flexibility and hydration of hyaluronic acid by molecular dynamics simulations.

Carbohydr Res 2020 Jul 11;493:108026. Epub 2020 May 11.

Center of Excellence in Computational Chemistry, Department of Chemistry, Faculty of Science, Chulalongkorn University, Bangkok, 10330, Thailand. Electronic address:

Hyaluronic acid (HA) is a biopolymer of disaccharide with two alternate glycosidic bonds, β(1,3) and β(1,4). A molecular dynamics study presented here unveiled conformational variability in association with the flexibility of the glycosidic linkers, which depends on the number of disaccharide units. HA chain maintains a rigid rod-like conformation with short chain lengths. Read More

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http://dx.doi.org/10.1016/j.carres.2020.108026DOI Listing

Novel bacterial cellulose membrane biosynthesized by a new and highly efficient producer Komagataeibacter rhaeticus TJPU03.

Carbohydr Res 2020 Jul 12;493:108030. Epub 2020 May 12.

National Engineering Technology Research Center for Preservation of Agricultural Products, Key Laboratory of Storage of Agricultural Products, Ministry of Agriculture and Rural Affairs, Tianjin Key Laboratory of Postharvest Physiology and Storage of Agricultural Products, Tianjin, 300384, China. Electronic address:

Bacterial cellulose(BC) is a kind of extracellular polymer synthesized by bacteria and it has very wide applications in many fields. However, the application of BC in a large commercial scale can still not be fulfilled due to the low yield and demanding for BC membranes with very different properties. To this end, a new BC-producer Komagataeibacter rhaeticus TJPU03 was isolated from rotten orange peel, which produced 8. Read More

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http://dx.doi.org/10.1016/j.carres.2020.108030DOI Listing

Hyaluronan decoration of milk exosomes directs tumor-specific delivery of doxorubicin.

Carbohydr Res 2020 Jul 12;493:108032. Epub 2020 May 12.

Key Laboratory of Carbohydrate Chemistry & Biotechnology, Ministry of Education, School of Biotechnology, Jiangnan University, 214122, Wuxi, China. Electronic address:

Milk exosomes (mExo), similar to cell-derived exosomes, are emerging as promising nanocarriers for delivery of therapeutic molecules such as chemical drugs and siRNA, due to the excellent biocompatibility and low-cost production from bovine milk. However, additional modification remains required to apply milk exosomes for tumor-specific drug delivery. Here, we attempted to develop a novel strategy for directing doxorubicin (Dox)-loaded mExo to CD44-overexpressing tumor cells. Read More

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http://dx.doi.org/10.1016/j.carres.2020.108032DOI Listing

Stereocontrolled total synthesis of iminosugar 1,4-dideoxy-1,4-imino-D-iditol.

Carbohydr Res 2020 Jun 1;492:108028. Epub 2020 May 1.

CNR-IBPM, "Sapienza" University of Rome, Dep. Chemistry, P.le A. Moro 5, 00185, Rome, Italy. Electronic address:

The first stereocontrolled total synthesis of iminosugar 1,4-dideoxy-1,4-imino-D-iditol is described. The key step in our approach was the double diastereoselection in the asymmetric dihydroxylation (AD) of suitable optically active olefin, the chiral vinyl azido alcohol 9. Performing the AD using the most common Cinchona alkaloids as ligands enabled us to identify the ligand of choice for the stereodivergent synthesis of 1,4-dideoxy-1,4-imino-D-iditol and 1,4-dideoxy-1,4-imino-D-galactitol. Read More

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http://dx.doi.org/10.1016/j.carres.2020.108028DOI Listing

Analysis of the susceptibility of reducing disaccharides composed of d-glucose to glycation using the Maillard reaction and a novel sensitive method that measures the percentage of the open-ring form.

Carbohydr Res 2020 Jul 28;493:108019. Epub 2020 Apr 28.

Department of Advanced Clinical Glycobiology, Graduate School of Medicine, Hokkaido University, Sapporo, 001-0021, Japan.

The susceptibility to glycation of all d-glucose-containing reducing disaccharides (kojibiose, sophorose, nigerose, laminaribiose, maltose, cellobiose, isomaltose, and gentiobiose) was evaluated by Maillard browning and the percentages of their acyclic forms estimated using a novel method to evaluate reactivity toward oxime formation were compared for the first time. This new method is facile and applicable to non-labeled carbohydrates, and it is extremely sensitive, more so than any other previously reported methods. The disaccharides linked by 1-6 bonds displayed both high browning intensity and oxime formation reactivity, and they had the greatest amount of the acyclic form. Read More

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http://dx.doi.org/10.1016/j.carres.2020.108019DOI Listing

Preparation and characterization of cellulose nanofiber cryogels as oil absorbents and enzymatic lipolysis scaffolds.

Carbohydr Res 2020 Jul 4;493:108020. Epub 2020 May 4.

Department of Chemical Science and Engineering, Graduate School of Engineering, Kobe University, Rokko, Nada-ku, Kobe, 657-8501, Japan. Electronic address:

Cellulose nanofiber (CNF) materials have received much attention as sustainable "green" materials with high mechanical properties. Their application in oil absorption and enzymatic lipolysis makes them further attractive from the perspective of environmental issues including marine pollution preservation. Herein, we prepared CNF cryogels with various surface properties, evaluated their capacities as oil absorbents and applied them as lipase-lipolysis scaffolds. Read More

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http://dx.doi.org/10.1016/j.carres.2020.108020DOI Listing

Novel disaccharide inhibitors for the bacterial galactosyltransferase LgtC: Design, synthesis via Heyns rearrangement, and biochemical evaluation.

Carbohydr Res 2020 Jun 20;492:108017. Epub 2020 Apr 20.

King's College London, School of Basic & Medical Biosciences, St John's Institute of Dermatology, 9th Floor Tower Wing, Guy's Hospital, London, SE1 9RT, United Kingdom; Queen's University Belfast, School of Pharmacy, Medical Biology Centre, 97 Lisburn Road, Belfast, BT9 7BL, United Kingdom. Electronic address:

Bacterial glycosyltransferases are potential targets for the development of novel antibiotics and anti-virulence agents. We report a novel inhibitor design for the retaining α-1,4-galactosyltransferase LgtC from Neisseria meningitidis. Our design is based on the installation of an electrophilic warhead on the LgtC acceptor substrate and targeted at a non-catalytic cysteine residue in the LgtC active site. Read More

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http://dx.doi.org/10.1016/j.carres.2020.108017DOI Listing

Rational targeting of Wzb phosphatase and Wzc kinase interaction inhibits extracellular polysaccharides synthesis and biofilm formation in Acinetobacter baumannii.

Carbohydr Res 2020 Jun 1;492:108025. Epub 2020 May 1.

Department of Biochemistry, Central University of Rajasthan, Bandarsindri, Ajmer, 305817, India. Electronic address:

Acinetobacter baumannii is an opportunistic nosocomial pathogen, and responsible for high mortality and morbidity. Biofilm formation is one of the resistance determinants, where extracellular polysaccharide (EPS) is an essential component. EPS synthesis and its export is regulated by the bacterial Wza-Wzb-Wzc system. Read More

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http://dx.doi.org/10.1016/j.carres.2020.108025DOI Listing

Direct formation and isolation of unprotected α-and β-d-ribopyranosyl urea, α-and β-d-ribofuranosyl urea, and a ribosyl-1,2-cyclic carbamate in carbohydrate melts.

Carbohydr Res 2020 Jun 29;492:108021. Epub 2020 Apr 29.

School of Science and Engineering,University of the Sunshine Coast, Locked Bag 4, Maroochydore DC, Queensland, 4558, Australia.

Solvent-free melts of unprotected d-ribose and urea generated mainly C- substituted ribosyl products. The remarkable resolving power of a graphitised-carbon HPLC column allowed products of the reaction formed over a range of heating times and temperatures to be monitored. Heating an uncatalysed mixture of d-ribose and urea at temperatures between 75 °C and 90 °C resulted in complex mixtures of compounds; after 19 h heating at 90 °C, up to ten components could be resolved. Read More

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http://dx.doi.org/10.1016/j.carres.2020.108021DOI Listing

A new strategy for the chemoenzymatic synthesis of glycopeptides by De-O-acetylation with an esterase and glycosylations with glycosyltransferases.

Carbohydr Res 2020 Jun 29;492:108023. Epub 2020 Apr 29.

Biotechnology Research Institute for Drug Discovery, Department of Life Science and Biotechnology, Advanced Industrial Science and Technology (AIST), 1-1-1 Higashi, Tsukuba, Ibaraki, 305-8565, Japan. Electronic address:

Glycopeptides are fragments of glycoproteins and are important in evaluating the biological roles of carbohydrates in glycoproteins. Fmoc solid-phase peptide synthesis using acetyl-protected glycosylated amino acids is a common strategy for the preparation of glycopeptides, but this approach normally requires chemical de-O-acetylation with a base that β-eliminates sugar residues and epimerizes the peptide backbone. Here we demonstrate a facile new chemoenzymatic synthetic strategy for glycopeptides, using an esterase for the de-O-acetylation of sugar residues and glycosyltransferases for successive sugar elongations at neutral pH. Read More

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http://dx.doi.org/10.1016/j.carres.2020.108023DOI Listing

Recent developments in chitosan encapsulation of various active ingredients for multifunctional applications.

Carbohydr Res 2020 Jun 12;492:108004. Epub 2020 Apr 12.

School of Biomedical Sciences, University of Ulster, Coleraine, BT52 1SA, Northern Ireland, UK.

Microencapsulation being an emerging technique has provided effective solution to the challenges faced by pharmaceutical, cosmetic, food agriculture and textile industries to deliver ingredients in their active forms to the target sites. Chitosan is a non-toxic, biodegradable and biocompatible amino polysaccharide which makes it useful for the encapsulation of various active ingredients with potential applications. Chitosan coating on food products, for example, gives them protection from possible antimicrobial attacks, antioxidants and extended shelf life. Read More

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http://dx.doi.org/10.1016/j.carres.2020.108004DOI Listing
June 2020
1.929 Impact Factor

A common strategy towards the synthesis of 1,4-dideoxy-1,4-imino-l-xylitol, deacetyl (+)-anisomycin and amino-substituted piperidine iminosugars.

Carbohydr Res 2020 Jun 25;492:107988. Epub 2020 Mar 25.

Department of Chemistry, Indian Institute of Technology Delhi, Hauz Khas, New Delhi, 110016, India. Electronic address:

A strategy towards the synthesis of three different target molecules, namely 1,4-dideoxy-1,4-imino-l-xylitol, deacetyl (+)-anisomycin and amino-substituted piperidine iminosugars, molecules of potential biological and medicinal significance, is reported from a common amino-vicinal diol intermediate derived from tri-O-benzyl-d-glucal. Construction of the key pyrrolidine ring present in 1,4-dideoxy-1,4-imino-l-xylitol and (+)-anisomycin was a consequence of thermodynamically driven concomitant intramolecular nucleophilic addition reaction of the amino group to the resultant aldehyde obtained by oxidative cleavage of the amino-vicinal diol. Alternatively, double nucleophilic substitution on an amino-diol, after mesylation, with various amines delivered amino-substituted piperidine iminosugars in good yields. Read More

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http://dx.doi.org/10.1016/j.carres.2020.107988DOI Listing

Total synthesis of Myc-IV(C16:0, S) via automated electrochemical assembly.

Carbohydr Res 2020 Jun 18;492:108018. Epub 2020 Apr 18.

Department of Chemistry and Biotechnology, Tottori University, 4-101 Koyamacho-minami, Tottori City, 680-8552, Tottori, Japan; Center for Research on Green Sustainable Chemistry, Tottori University, 4-101 Koyamacho-minami, Tottori City, 680-8552, Tottori, Japan. Electronic address:

Total synthesis of Myc-IV(C16:0, S) via automated electrochemical assembly has been accomplished. This tetrasaccharide has been studied as a symbiotic signal molecule of Arbuscular Mycorrhiza fungi. We have achieved stereoselective synthesis of a disaccharide building block using the mixed-electrolyte system for electrochemical glycosylation; 2 + 1+1 strategy enables us to access the tetrasaccharide precursor and complete the synthesis Myc-IV(C16:0, S) efficiently. Read More

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http://dx.doi.org/10.1016/j.carres.2020.108018DOI Listing

Chemo-enzymatic route to bridged homolyxofuranosyl-pyrimidines.

Carbohydr Res 2020 Jun 16;492:108013. Epub 2020 Apr 16.

Bioorganic Laboratory, Department of Chemistry, University of Delhi, Delhi, 110 007, India. Electronic address:

Synthesis of 2'-O,5'-C-bridged-β-d-homolyxofuranosyl nucleosides U and T have been achieved starting from diacetone-d-glucose in overall yields 55.7 and 57.1%, respectively. Read More

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http://dx.doi.org/10.1016/j.carres.2020.108013DOI Listing
June 2020
1.929 Impact Factor

Enzyme-aided xylan extraction from alkaline-sulfite pretreated sugarcane bagasse and its incorporation onto eucalyptus kraft pulps.

Carbohydr Res 2020 Jun 8;492:108003. Epub 2020 Apr 8.

Departamento de Biotecnologia, Escola de Engenharia de Lorena, Universidade de São Paulo, 12602-810, Lorena, SP, Brazil. Electronic address:

Hemicellulose-rich substrates produced in the lignocellulose biorefinery context can yield macromolecular xylan structures with assorted application in the chemical industry. Xylan presents natural affinity to cellulose and its incorporation onto fibers increases the physical processability of pulp; however, current studies diverge on how molar mass affects xylan interaction with cellulose. In the current work, xylans with varied structural characteristics were prepared from alkaline-sulfite pretreated sugarcane bagasse with aid of an alkaline-active xylanase and selective precipitations using different ethanol concentrations. Read More

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http://dx.doi.org/10.1016/j.carres.2020.108003DOI Listing

Three new acylphloroglucinol glucosides from the roots of Lysidice rhodostegia and their antioxidant activities.

Carbohydr Res 2020 Jun 14;492:108012. Epub 2020 Apr 14.

Institute of Traditional Chinese Medicine & Natural Products, College of Pharmacy, Jinan University, Guangzhou, 510632, China. Electronic address:

Three new acylphloroglucinol glucosides, rhodosides A-C (1-3), and three known ones (4-6) were isolated from the roots of Lysidice rhodostegia. The new structures were identified by MS, NMR, and acid hydrolysis. In addition, the antioxidant capacities of the isolated compounds were evaluated using DPPH radical-scavenging assay, and compounds 1-6 exhibited obvious antioxidant activities with IC values of 24. Read More

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http://dx.doi.org/10.1016/j.carres.2020.108012DOI Listing

Formation of glyco-functionalized interfaces for protein binding using polyphenolic glycoside.

Carbohydr Res 2020 Jun 3;492:108002. Epub 2020 Apr 3.

Department of Chemical Engineering, Fukuoka University, 8-19-1 Nanakuma, Jonan-ku, Fukuoka, 814-0180, Japan.

In this study, a polyphenolic glycoside (α-glucosyl rutin) was used to form glyco-functionalized interfaces for protein binding. α-Glucosyl rutin was coated onto precious metals, metal oxides, and synthetic polymers, including polyethylene and polytetrafluoroethylene with poor surface modifiability. The glyco-functionalized interfaces bound strongly and specifically to concanavalin A and Bauhinia purpurea lectin, which have different carbohydrate specificities. Read More

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http://dx.doi.org/10.1016/j.carres.2020.108002DOI Listing

Structure of a heptose-containing polysaccharide derived from Komagataeibacter europaeus NBRC 3261.

Carbohydr Res 2020 Jun 27;492:107989. Epub 2020 Mar 27.

Department of Chemistry, Biotechnology, and Chemical Engineering, Kagoshima University, Kagoshima, Japan. Electronic address:

An O-antigen polysaccharide fraction (Ke-PS) was isolated from Komagataeibacter europaeus NBRC 3261. In addition to chemical analyses, its structure was characterized by 1D and 2D H as well as C NMR spectroscopy. The polysaccharide is composed of linear disaccharide repeating unit that consists of d-galactose and d-glycero-d-manno-heptose: →7)-α-d,d-Hepp-(1 → 2)-α-d-Galp-(1 → . Read More

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http://dx.doi.org/10.1016/j.carres.2020.107989DOI Listing

Comparative immunological studies of tumor-associated Lewis X, Lewis Y, and KH-1 antigens.

Carbohydr Res 2020 Jun 31;492:107999. Epub 2020 Mar 31.

Department of Chemistry, University of Florida, 214 Leigh Hall, Gainesville, FL, 32611, United States. Electronic address:

Tumor-associated carbohydrate antigens Lewis X (Le), Lewis Y (Le), and KH-1 are useful targets for cancer immunotherapy. In this regard, an insight into the structure-immunogenicity relationships of these antigens is important but this has not been systematically investigated yet. In the current study, Le, Le, and KH-1 antigens with a lactose unit at the reducing end as a spacer were synthesized and coupled with keyhole limpet hemocyanin (KLH) protein. Read More

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http://dx.doi.org/10.1016/j.carres.2020.107999DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC7261630PMC

Design, synthesis, characterization and biological evaluation of Thieno[2,3-b]pyridines-chitosan nanocomposites as drug delivery systems for colon targeting.

Carbohydr Res 2020 Jun 29;492:107990. Epub 2020 Mar 29.

Department of Chemistry, Faculty of Science, Kafrelsheikh University, Kafrelsheikh, 33516, Egypt.

Thieno[2,3-b]pyridine derivatives DATP have been synthesized based on Thorpe-Ziegler Cyclization. The reaction of arylidene malononitrile derivatives (I) with thiocyanoacetamide (II) in basic medium (piperidine) followed by alkylation using ethyl chloroacetate and finally, cyclization in sodium ethoxide yielded DATP. Thieno[2,3-b]pyridine-chitosan nanocomposites CS-DATP were prepared from the DATP and CS nanoparticles using sodium tripolyphosphate (TPP). Read More

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http://dx.doi.org/10.1016/j.carres.2020.107990DOI Listing

Synthesis and biological evaluation of novel urea, thiourea and squaramide diastereomers possessing sugar backbone.

Carbohydr Res 2020 Jun 29;492:107991. Epub 2020 Mar 29.

Department of Bioengineering, Kırıkkale University, 71450, Yahşihan, Kırıkkale, Turkey.

A series of novel chiral 14 urea, thiourea and squaramide stereoisomers possessing carbohydrate backbones as well as amide functional groups was synthesized and characterized by their, H NMR, C NMR, FT-IR, HRMS, optical rotation, and melting points. Their antiproliferative activities were investigated against HeLa and PC3 cell lines. The compounds 9, 11 and 12 showed better activities at 25 μM against PC3 cell line with respect to the standard 5-fluorouracil (5-FU). Read More

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http://dx.doi.org/10.1016/j.carres.2020.107991DOI Listing

Isolation and optimization of the method for industrial production of chitin and chitosan from Omani shrimp shell.

Carbohydr Res 2020 Jun 2;492:108001. Epub 2020 Apr 2.

Department of Biological Sciences and Chemistry, College of Arts and Science, University of Nizwa, P.O. Box 33, Postal Code 616, Nizwa, Oman.

Chitosan is an organic compound widely used in biomedical and agricultural fields due to its medicinal values. Chitosan is the largest biopolymer after cellulose and it is used as a food supplement as well as a primary health care product. The focus of the present study is to optimize the method for isolation and characterization of chitosan from Omani shrimp shell. Read More

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http://dx.doi.org/10.1016/j.carres.2020.108001DOI Listing

The non-covalent complexes of α- or γ-cyclodextrin with divalent metal cations determined by mass spectrometry.

Carbohydr Res 2020 Jun 20;492:107987. Epub 2020 Mar 20.

Department of Chemistry, Fudan University, Shanghai, 200433, China; Institute of Mass Spectrometry, Ningbo University, Ningbo, Zhejiang, 315211, China. Electronic address:

Noncovalent complexes between cyclodextrin (CD) and divalent metal cations drew growing attentions due to their applications in the pharmaceutical industry for molecular recognition. In this study, gas-phase binding of noncovalent complexes between α-, or γ-CD and divalent metal cations was investigated by electrospray ionization mass spectrometry (ESI-MS), demonstrating the formation of 1:1 stoichiometric noncovalent complexes. The binding of the complexes were furtherly confirmed by collision-induced dissociation (CID) with tandem mass spectrometry. Read More

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http://dx.doi.org/10.1016/j.carres.2020.107987DOI Listing

Guar gum cinnamate ouzo nanoparticles for bacterial contact killing in water environment.

Carbohydr Res 2020 May 15;491:107983. Epub 2020 Mar 15.

Division of Pharmaceutical and Fine Chemical Technology, Department of Chemical Technology, University of Calcutta, 92, A.P.C. Road, Kolkata, 700009, West Bengal, India; Department of Biotechnology, Maulana Abul Kalam Azad University of Technology, NH 12, Haringhata, Nadia, 721249, West Bengal, India. Electronic address:

Herein we report the synthesis of newer guar gum cinnamate esters (GGC) following a Hofmeister cation guided homogeneous phase reaction. High degree of substitution (DS) guar gum cinnamate was obtained using, cinnamic acid halide reactant at a 1:3 M ratio. The biopolymer was fully characterized in FT-IR,C NMR, XRD and thermal analysis. Read More

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http://dx.doi.org/10.1016/j.carres.2020.107983DOI Listing

Synthesis of biomass-based carbon aerogels in energy and sustainability.

Carbohydr Res 2020 May 20;491:107986. Epub 2020 Mar 20.

School of the Environment and Safety Engineering, Jiangsu University, Zhenjiang, 212013, PR China. Electronic address:

Carbon aerogels are 3D hierarchical multiscale porous materials with outstanding physicochemical properties such as high specific surface area, low density, high porosity, excellent electrical conductor, good chemical stability, hydrophobicity, and adjustable surface chemistry among others. Unlike conventional carbon aerogels, biomass-based carbon aerogels are economical, environmentally friendly and have nigh inexhaustible precursors, which have generated extensive interest and exhibited outstanding electrocatalysis and adsorption/absorption performance. In this review, we mainly summarized the four main kinds of biomass (cellulose, chitosan, lignin and tannin) as carbon aerogel precursor, and discussed in detail their resource, constitute and optimized synthesis mechanism. Read More

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http://dx.doi.org/10.1016/j.carres.2020.107986DOI Listing
May 2020
1.929 Impact Factor

Multi-spectroscopic investigation on the inclusion complexation of α-cyclodextrin with long chain ionic liquid.

Carbohydr Res 2020 May 19;491:107982. Epub 2020 Mar 19.

School of Studies in Chemistry, Pt. Ravishankar Shukla University, Raipur, CG, 492010, India. Electronic address:

Host-guest interaction of ionic liquid (IL) 1-decyl-3-methylimidazolium tetrafluoroborate [Dmim][BF] within α-cyclodextrin (α-CD) has been studied by different spectroscopic techniques and our investigated system is significant in the field of supramolecular chemistry and medicine. Benesi-Hildebrand correlation is used to study the stoichiometry of the host-guest complexation. Here concurrence with FT-IR and dynamic light scattering (DLS) results, it is shown that α-CD interacts with [Dmim][BF], induces compositional and structural changes. Read More

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http://dx.doi.org/10.1016/j.carres.2020.107982DOI Listing
May 2020
1.929 Impact Factor

Preparation of O-Glycopeptides from commercial bovine whey proteins using offline liquid chromatography-Mass spectrometry.

Carbohydr Res 2020 May 19;491:107981. Epub 2020 Mar 19.

Laboratory of Glyco-Organic Chemistry, The Noguchi Institute, 1-9-7 Kaga, Itabashi-ku, Tokyo, Japan.

O-Glycopeptides derived from natural bioresources are an attractive material for a variety of purposes. Whey protein products are used as a human dietary supplement and in animal feed and are a readily available resource for the preparation of O-glycopeptides. The protein composition of bovine milk is well-studied, and many glycoproteins carrying N-glycans and O-glycans have been found in commercial whey protein products. Read More

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http://dx.doi.org/10.1016/j.carres.2020.107981DOI Listing