10,161 results match your criteria Carbohydrate research[Journal]


Bivalent glycoconjugates based on 1,5-diazabicyclo[3.3.0]octa-3,6-diene-2,8-dione ("bimane") as a central scaffold.

Carbohydr Res 2019 Jan 8;473:88-98. Epub 2019 Jan 8.

Department of Organic Chemistry, University of Debrecen, H-4032, Debrecen, Egyetem tér 1, Hungary. Electronic address:

The heteroaromatic fused diazabicyclic "bimane" ring system, discovered four decades ago, is endowed with remarkable chemical and photophysical properties. No carbohydrate derivatives of bimanes have, however, been described thus far. Here we report on the syntheses of a range of bimanes decorated with various glycosyl residues. Read More

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http://dx.doi.org/10.1016/j.carres.2019.01.002DOI Listing
January 2019

Probing peptide substrate specificities of N-glycosyltranferase isoforms from different bacterial species.

Carbohydr Res 2018 Dec 30;473:82-87. Epub 2018 Dec 30.

The State Key Laboratory of Microbial Technology, National Glycoengineering Research Center, Shandong University, Qingdao, Shandong, 266237, China. Electronic address:

N-glycosyltransferase (NGT) is responsible for transferring hexose monosaccharides to the asparagine side chain of proteins and polypeptides in the consensus sequon (N-(X≠P)-T/S) with nucleotide-activated sugars as donor substrates. Here, we expressed and purified four different N-glycosyltransferases derived from diverse bacteria, including Actinobacillus pleuropneumoniae, Aggregatibacter aphrophilus, Kingella kingae and Bibersteinia trehalosi, and measured their catalytic activities of four synthesized peptides via in vitro glycosylation assays. RP-HPLC and mass spectrometry were used to identify and quantify the glycopeptide formation by distinct NGT isoforms. Read More

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http://dx.doi.org/10.1016/j.carres.2018.12.016DOI Listing
December 2018

Recent advances in reagent-controlled stereoselective/stereospecific glycosylation.

Carbohydr Res 2018 Oct 22;473:72-81. Epub 2018 Oct 22.

Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, 637371, Singapore. Electronic address:

The formation of O-glycosidic linkage is arguably one of the most important topics in glycoscience due to the prevalence of O-glycosides in nature. Great efforts have been devoted to this field by many carbohydrate chemists to develop stereoselective/stereospecific glycosylation methodologies. Although glycosyl donor- and acceptor-controlled strategies have significantly progressed, the tedious design and pre-synthesis of substrates could not be avoided. Read More

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https://linkinghub.elsevier.com/retrieve/pii/S00086215183056
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http://dx.doi.org/10.1016/j.carres.2018.10.006DOI Listing
October 2018
2 Reads

Treatment of recalcitrant crystalline polysaccharides with lytic polysaccharide monooxygenase relieves the need for glycoside hydrolase processivity.

Carbohydr Res 2019 Jan 7;473:66-71. Epub 2019 Jan 7.

Department of Chemistry, Biotechnology and Food Science, Norwegian University of Life Sciences, PO 5003, N-1432, Ås, Norway. Electronic address:

Processive glycoside hydrolases associate with recalcitrant polysaccharides such as cellulose and chitin and repeatedly cleave glycosidic linkages without fully dissociating from the crystalline surface. The processive mechanism is efficient in the degradation of insoluble substrates, but comes at the cost of reduced enzyme speed. We show that less processive chitinase variants with reduced ability to degrade crystalline chitin, regain much of this ability when combined with a lytic polysaccharide monooxygenase (LPMO). Read More

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http://dx.doi.org/10.1016/j.carres.2019.01.001DOI Listing
January 2019

Palladium catalyzed synthesis of sugar-fused indolines via C(sp)-H/NH activation.

Carbohydr Res 2019 Jan 4;473:57-65. Epub 2019 Jan 4.

Department of Chemistry, Indian Institute of Technology Kanpur, Kanpur, 208016, India. Electronic address:

A simple Pd(OAc) catalyzed strategy for the synthesis of sugar-fused indolines from 2-N-oxalylamido-2-deoxy-C-aryl glycosides is reported by utilizing N-oxalylamido group as an auxiliary via C(sp)-H/NH Activation. The reaction is successfully applied on glucose as well as galactose derived differently substituted 2-N-oxalylamido-2-deoxy-C-aryl glycosides to give sugar-fused indolines in moderate to good yields. The utility of this strategy in the synthesis of sugar-fused indoles is also described. Read More

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http://dx.doi.org/10.1016/j.carres.2018.12.015DOI Listing
January 2019
1.929 Impact Factor

Purification and biochemical characterization of a novel acido-halotolerant and thermostable endochitinase from Melghiribacillus thermohalophilus strain Nari2A.

Carbohydr Res 2018 Dec 29;473:46-56. Epub 2018 Dec 29.

Laboratory of Cellular and Molecular Biology, Microbiology Team, Faculty of Biological Sciences (FSB), University of Sciences and Technology of Houari Boumediene (USTHB), PO Box 32, El Alia, Bab Ezzouar, 16111, Algiers, Algeria. Electronic address:

An extracellular acido-thermostable endochitinase (called ChiA-Mt45) from thermohalophilic Melghiribacillus thermohalophilus strain Nari2A gen. nov. sp. Read More

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https://linkinghub.elsevier.com/retrieve/pii/S00086215183069
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http://dx.doi.org/10.1016/j.carres.2018.12.017DOI Listing
December 2018
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Structure determination of Streptococcus suis serotypes 7 and 8 capsular polysaccharides and assignment of functions of the cps locus genes involved in their biosynthesis.

Carbohydr Res 2018 Dec 18;473:36-45. Epub 2018 Dec 18.

Swine and Poultry Infectious Diseases Research Center, Faculty of Veterinary Medicine, University of Montreal, 3200 Sicotte St., St-Hyacinthe, Quebec, J2S 2M2, Canada; Canadian Glycomics Network (GlycoNet), University of Alberta, 11227 Saskatchewan Dr., Edmonton, Alberta, T6G 2G2, Canada. Electronic address:

Streptococcus suis serotypes 7 and 8 are counted among the top six S. suis serotypes causing clinical disease in pigs. Yet, limited information is available on these serotypes. Read More

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http://dx.doi.org/10.1016/j.carres.2018.12.009DOI Listing
December 2018

NMR solution geometry of saccharides containing the 6-O-(α-D-glucopyranosyl)-α/β-D-glucopyranose (isomaltose) or 6-O-(α-D-galactopyranosyl)-α/β-D-glucopyranose (melibiose) core.

Carbohydr Res 2018 Dec 22;473:18-35. Epub 2018 Dec 22.

Department of Chemistry, University of the Pacific, 3601 Pacific Avenue, Stockton, CA 95211, USA. Electronic address:

The solution geometries of D-Glcp, Me-D-Glcp, 6-O-Me-D-Glcp, Me-6-O-Me-D-Glcp, D-Glcp-(α-1,6)-D-Glcp (isomaltose), D-Glcp-(α-1,6)-D-Glcp-(α-1,6)-D-Glcp (isomaltotriose), D-Galp-(α-1,6)-D-Glcp (melibiose), D-Galp-(α-1,6)-D-Glcp-(α-1,2)-D-Fruf (raffinose), and D-Galp-(α-1,6)-D-Galp-(α-1,6)-D-Glcp-(α-1,2)-D-Fruf (stachyose) in water are described by NMR spectroscopy, molecular dynamic simulations and quantum mechanical calculations. Overall, a change in anomeric configuration at the reducing end and/or anomeric substitution (methylation) changed the conformational space of the terminal CHOH group significantly. Conformational analysis of the free monosaccharides matched literature results very well. Read More

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http://dx.doi.org/10.1016/j.carres.2018.12.012DOI Listing
December 2018

Synthesis of a hexasaccharide repeating unit of the cell wall polysaccharide of Bifidobacterium animalis subsp. lactis LKM512.

Carbohydr Res 2018 Dec 25;473:12-17. Epub 2018 Dec 25.

Bose Institute, Division of Molecular Medicine, P-1/12, C.I.T. Scheme VII-M, Kolkata, 700054, India. Electronic address:

A convergent synthesis of the hexasaccharide as its 2-aminoethyl glycoside corresponding to the repeating unit of the cell wall polysaccharide of Bifidobacterium animalis subsp. lactis LKM512 has been achieved applying a [4 + 2] glycosylation strategy. The disaccharide thioglycoside donor was prepared by combining a d-galactofuranosyl thioglycoside with another l-rhamnosyl thioglycoside acceptor. Read More

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http://dx.doi.org/10.1016/j.carres.2018.12.014DOI Listing
December 2018

Structures of cell-wall glycopolymers of Lactobacillus rhamnosus BIM B-1039.

Carbohydr Res 2018 Dec 10;472:138-143. Epub 2018 Dec 10.

N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia.

Glycopolymers of two types were isolated from the cell wall of Lactobacillus rhamnosus BIM B-1039 by stepwise extraction with cold and hot 10% aq CClCOH followed by anion-exchange gel chromatography. The following structures of the glycopolymers were established by sugar analysis, Smith degradation and 1D and 2D NMR spectroscopy. Read More

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http://dx.doi.org/10.1016/j.carres.2018.12.006DOI Listing
December 2018

The characterisation of a galactokinase from Streptomyces coelicolor.

Carbohydr Res 2018 Dec 14;472:132-137. Epub 2018 Dec 14.

Department of Chemistry, University of York, Heslington, York, YO10 5DD, UK.

Promiscuous galactokinases (GalKs), which catalyse the ATP dependent phosphorylation of galactose in nature, have been widely exploited in biotechnology for the rapid synthesis of diverse sugar-1-phosphates. This work focuses on the characterisation of a bacterial GalK from Streptomyces coelicolor (ScGalK), which was overproduced in Escherichia coli and shown to phosphorylate galactose. ScGalK displayed a broad substrate tolerance, with activity towards Gal, GalN, Gal3D, GalNAc, Man and L-Ara. Read More

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http://dx.doi.org/10.1016/j.carres.2018.12.005DOI Listing
December 2018

Chiron approach from D-mannitol to access a diastereomer of the reported structure of an acetogenin, an amide alkaloid and a sex pheromone.

Carbohydr Res 2018 Dec 14;473:5-11. Epub 2018 Dec 14.

Department of Chemistry, Jadavpur University, Jadavpur, Kolkata, 700032, West Bengal, India. Electronic address:

A short, simple and convenient chiron approach to (3R,4S,5R)-(-)-3,5-dihydroxy-4-decanolide, a hitherto unknown diastereomer of the reported structure of a naturally occurring acetogenin, (+)-polyporolide has been accomplished starting from a commercially available, inexpensive chiral pool molecule D-(+)-mannitol in nine efficient steps. An advanced intermediate synthesized from D-(+)-mannitol in six steps toward this end was further employed successfully to access two different natural products bearing two contiguous stereogenic centers. As a result, first chiron approach to formal total synthesis of an amide alkaloid, (4R,5R,2E)-4,5-dihydroxy-1-(piperidin-1-yl)dec-2-en-1-one and total synthesis of a male sex pheromone in parasitic Hymenoptera, (4R,5R)-(-)-5-hydroxy-4-decanolide have also been achieved. Read More

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http://dx.doi.org/10.1016/j.carres.2018.12.008DOI Listing
December 2018

Structure of the O-specific polysaccharide from a halophilic bacterium Halomonas ventosae RU5S2EL.

Carbohydr Res 2018 Dec 15;473:1-4. Epub 2018 Dec 15.

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

Halomonas ventosae RU5S2EL, a halophilic Gram-negative bacterium isolated from salt sediments of lake Elton (Russia), was cultivated and the lipopolysaccharide was extracted by the Westphal procedure. The O-specific polysaccharide (OPS) was obtained 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 as well as Smith degradation. The OPS was found to consist of branched pentasaccharide repeating units of the following structure. Read More

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http://dx.doi.org/10.1016/j.carres.2018.12.010DOI Listing
December 2018

Substrate binding versus escape dynamics in a pH-affected fungal beta-glucosidase revealed by molecular dynamics simulations.

Carbohydr Res 2018 Dec 11;472:127-131. Epub 2018 Dec 11.

Department of Biological and Environmental Engineering, College of Agriculture and Life Sciences, Cornell University, Ithaca, NY, USA. Electronic address:

The cellulolytic ability of fungal species is important to both natural and engineered biocycling of plant matter. One essential step is the conversion of cellobiose into glucose catalyzed by beta-glucosidases. Mutagenesis studies have implicated altering the substrate binding pocket to influence the pH-activity profile of this enzyme. Read More

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http://dx.doi.org/10.1016/j.carres.2018.12.007DOI Listing
December 2018
1.929 Impact Factor

Synthesis of nortropane alkaloid calystegine B from methyl α-d-xylopyranoside.

Carbohydr Res 2018 Dec 7;472:122-126. Epub 2018 Dec 7.

Department of Chemistry, Aarhus University, Langelandsgade 140, 8000, Aarhus C, Denmark. Electronic address:

A new synthetic route for formation of a central cycloheptanone intermediate leading to the nortropane alkaloid calystegine B is described. The approach installs the desired ketone functionality directly in a ring-closing metathesis step. The target compound was prepared over 10 steps from commercially available methyl α-d-xylopyranoside. Read More

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http://dx.doi.org/10.1016/j.carres.2018.12.002DOI Listing
December 2018

Facile chemoenzymatic synthesis of Lewis a (Le) antigen in gram-scale and sialyl Lewis a (sLe) antigens containing diverse sialic acid forms.

Carbohydr Res 2018 Dec 9;472:115-121. Epub 2018 Dec 9.

Department of Chemistry, University of California, One Shields Avenue, Davis, CA, 95616, USA. Electronic address:

An efficient streamlined chemoenzymatic approach has been developed for gram-scale synthesis of Lewis a angtigen (LeβProN) and a library of sialyl Lewis a antigens (sLeβProN) containing different sialic acid forms. Intially, commercially available inexpensive N-acetylglucosamine (GlcNAc) was converted to its N'-glycosyl p-toluenesulfonohydrazide in one step. Followed by chemical glycosylation, GlcNAcβProN was synthesized using this protecting group-free method in high yield (82%). Read More

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https://linkinghub.elsevier.com/retrieve/pii/S00086215183064
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http://dx.doi.org/10.1016/j.carres.2018.12.004DOI Listing
December 2018
3 Reads

A novel and environmental friendly synthetic route for hydroxypyrrolidines using zeolites.

Carbohydr Res 2018 Dec 4;472:103-114. Epub 2018 Dec 4.

Department of Chemistry, National University of Singapore, 3 Science Drive 3, 117543, Singapore.

A critical step in the synthesis of the hydroxypyrrolidines, 1,4-dideoxy-1,4-imino-l-lyxitol and 1,4-dideoxy-1,4-imino-d-lyxitol, from the corresponding d-sugars is the synthesis of O-methyl 2,3-O-isopropylidenepentofuranoses. Instead of applying homogeneous catalysis process with conventional inorganic acid catalysts like HCl and HClO, it was found that heterogeneous catalysis using zeolites could be used for the one-pot synthesis of O-methyl 2,3-O-isopropylidenepentofuranoses directly from d-sugars, MeOH and acetone at mild condition. The best catalyst was H-beta zeolite containing a Si/Al molar ratio of 150, where a yield of >83% was obtained. Read More

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http://dx.doi.org/10.1016/j.carres.2018.11.016DOI Listing
December 2018
1 Read

Structure elucidation and gene cluster annotation of the O-antigen of Vibrio cholerae O100 containing two rarely occurred amino sugar derivatives.

Carbohydr Res 2018 Nov 5;472:98-102. Epub 2018 Nov 5.

TEDA Institure of Biological Sciences and Biotechnology, Nankai University, TEDA, Tianjin, China.

O-polysaccharide (O-antigen) was isolated from the lipopolysaccharide of Vibrio cholerae O100 and studied by component analyses and 1D and 2D NMR spectroscopy. The following structure of the O-polysaccharide was established: →3)-β-d-QuipNAc4N(dHh)-(1 → 3)-α-d-Fucp4N(RHb)-(1 → 3)-α-l-FucpNAc-(1→ where Hb and dHh indicate 3-hydroxybutanoyl and 3,5-dihydroxyhexanoyl, respectively. The O-antigen gene cluster of V. Read More

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http://dx.doi.org/10.1016/j.carres.2018.11.001DOI Listing
November 2018
1 Read

Structural characterization of a complex triterpenoid saponin from Albizia lebbeck and investigation of its permeability property and supramolecular interactions with membrane constituents.

Carbohydr Res 2019 Jan 27;471:105-114. Epub 2018 Nov 27.

Laboratório de Química de Plantas Medicinais, Instituto de Pesquisas de Produtos Naturais, Centro de Ciências da Saúde, Universidade Federal do Rio de Janeiro, P.O. Box 68045, CEP 21941-971, Rio de Janeiro, Brazil. Electronic address:

As part of the ongoing efforts in discovering potentially bioactive natural products from medicinal plants, the present study was conducted to isolate a new complex triterpenoid saponin from the barks of Albizia lebbeck. It was isolated by using chromatographic methods and its structural elucidation was performed using detailed analyses of H and C NMR spectra including 2D-NMR (COSY, TOCSY, HSQC and HMBC) spectroscopic techniques, high-resolution electrospray ionization mass spectrometry (HRESIMS) analysis and chemical conversions. Its structure was established as 21-[[(2E,6S)-6-[6-deoxy-4-O-[(2E,6S)-6-hydroxy-2-(hydroxymethyl)-6-methyl-1-oxo-2,7-octadienyl]-[(β-d-glucopyranosyl)oxy]-2-(hydroxymethyl)-6-methyl-1-oxo-2,7-octadienyl]-[(β-d-glucopyranosyl)oxy]-2,6-dimethyl-1-oxo-2,7-octadienyl]oxy]-16-hydroxy-3-[[O-β-d-xylopyranosyl-(1 → 2)-O-α-l-arabinopyranosyl-(1 → 6)-2-(acetylamino)-2-deoxy-β-d-glucopyranosyl]oxy]-(3β,16α,21β)-olean-12-en-28-oic acid O-α-l-arabinofuranosyl-(1 → 4)-O-[β-d-glucopyranosyl-(1 → 3)]-O-6-deoxy-α-l-mannopyranosyl-(1 → 2)-β-d-glucopyranosyl ester (1). Read More

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http://dx.doi.org/10.1016/j.carres.2018.11.015DOI Listing
January 2019

Strategies for chemoenzymatic synthesis of carbohydrates.

Carbohydr Res 2018 Nov 24;472:86-97. Epub 2018 Nov 24.

Department of Chemistry, University of California, Davis, One Shields Avenue, Davis, CA, 95616, USA. Electronic address:

Carbohydrates are structurally complex but functionally important biomolecules. Therefore, they have been challenging but attractive synthetic targets. While substantial progress has been made on advancing chemical glycosylation methods, incorporating enzymes into carbohydrate synthetic schemes has become increasingly practical as more carbohydrate biosynthetic and metabolic enzymes as well as their mutants with synthetic application are identified and expressed for preparative and large-scale synthesis. Read More

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http://dx.doi.org/10.1016/j.carres.2018.11.014DOI Listing
November 2018
1 Read

Stereoselective synthesis and antiproliferative activity of the isomeric sphinganine analogues.

Carbohydr Res 2018 Nov 28;472:76-85. Epub 2018 Nov 28.

Institute of Geotechnics, Slovak Academy of Sciences, Watsonova 45, 040 01, Košice, Slovak Republic.

A flexible synthetic approach to biologically active sphingoid base-like compounds with a 3-amino-1,2-diol framework was achieved through a [3,3]-sigmatropic rearrangement and late stage olefin cross-metathesis as the key transformations. The stereochemistry of the newly created stereogenic centre was assigned via a single crystal X-ray analysis of the (4S,5R)-5-(hydroxymethyl)-4-vinyloxazolidine-2-thione. In order to rationalise the observed stereoselectivity of the aza-Claisen rearrangement, DFT calculations were carried out. Read More

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http://dx.doi.org/10.1016/j.carres.2018.09.008DOI Listing
November 2018

Janus glycosides of next generation: Synthesis of 4-(3-chloropropoxy)phenyl and 4-(3-azidopropoxy)phenyl glycosides.

Carbohydr Res 2019 Jan 25;471:95-104. Epub 2018 Nov 25.

N. D. Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences, Leninsky prosp., 47, 119991, Moscow, Russian Federation. Electronic address:

Efficient procedures for the preparative synthesis of per-O-acyl derivatives of 4-(3-chloropropoxy)phenyl (CPP) glycosides of a series of common mono- and disaccharides (d-glucose, d-galactose, d-mannose, l-rhamnose, d-arabinofuranose, d-glucosamine, lactose) are described. The CPP glycosides obtained were transformed in almost quantitative yields to the corresponding unprotected 4-(3-azidopropoxy)phenyl (APP) glycosides, which could become next-generation Janus glycosides with cleavable spacer aglycon, ready for conjugation or further transformation. Read More

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http://dx.doi.org/10.1016/j.carres.2018.11.013DOI Listing
January 2019
1.929 Impact Factor

Lewis acid promoted anomerisation of alkyl O- and S-xylo-, arabino- and fucopyranosides.

Carbohydr Res 2019 Jan 24;471:85-94. Epub 2018 Nov 24.

School of Chemistry, National University of Ireland Galway, University Road, Galway, H91 TK33, Ireland. Electronic address:

Pentopyranoside and 6-deoxyhexopyranosides, such as those from d-xylose, l-arabinose and l-fucose are components of natural products, oligosaccharides or polysaccharides. Lewis acid promoted anomerisation of some of their alkyl O- and S-glycopyranosides is reported here. SnCl was more successful than TiCl, with the latter giving the glycosyl chloride by-product in some cases, and both were superior to BFOEt. Read More

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https://linkinghub.elsevier.com/retrieve/pii/S00086215183060
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http://dx.doi.org/10.1016/j.carres.2018.11.010DOI Listing
January 2019
8 Reads

Effective analysis of degree of polymerization of polysialic acids in mass spectrometry by combining novel sample preparation and dynamic instrument optimization methods.

Carbohydr Res 2019 Jan 17;471:78-84. Epub 2018 Nov 17.

Institute of Biochemistry and Molecular Biology, National Yang-Ming University, Taipei, 112, Taiwan, ROC; Genomics Research Center, Academia Sinica, No. 128, Academia Road, Section 2, Nankang District, Taipei, 115, Taiwan, ROC. Electronic address:

This work demonstrates a mass spectrometry technique to improve data reliability when analyzing degree of polymerization (DP) of high-mass polysialic acids (PSAs). Matrix-assisted laser-desorption/ionization (MALDI) time-of-flight mass spectrometry is the technique of choice for analyzing large molecules due to its wide mass working range; however, the observed DP of PSAs using such an instrument is unreliable owing to sensitivity bias towards low-mass ions. A multi-layer MALDI sample preparation protocol is demonstrated in the current study to improve PSA sensitivity, and a dynamic instrument optimization method (DIOM) is employed to minimize detector saturation over a wide mass range. Read More

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http://dx.doi.org/10.1016/j.carres.2018.11.009DOI Listing
January 2019

Recent advances in site-selective functionalization of carbohydrates mediated by organocatalysts.

Carbohydr Res 2019 Jan 23;471:64-77. Epub 2018 Nov 23.

School of Pharmacy, University of Wisconsin-Madison, Madison, WI, 53705, USA; Department of Chemistry, University of Wisconsin-Madison, Madison, WI, 53706, USA. Electronic address:

As one of the four fundamental building blocks of life, carbohydrates assume varied and expansive roles in biological contexts. More in-depth understanding of carbohydrates and their interactions, however, is often restricted by our inability to synthesize and subsequently functionalize them in a site-selective manner. This review will summarize recent advances in the site-selective functionalization of carbohydrates using organocatalysts, including achiral catalysts, chiral nucleophilic bases, chiral N-heterocyclic carbenes, and chiral phosphoric acids, with an emphasis on the catalytic nature in each case. Read More

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http://dx.doi.org/10.1016/j.carres.2018.11.012DOI Listing
January 2019

N-acetyltransferases from three different organisms displaying distinct selectivity toward hexosamines and N-terminal amine of peptides.

Carbohydr Res 2018 Nov 22;472:72-75. Epub 2018 Nov 22.

College of Pharmacy and Tianjin Key Laboratory of Molecular Drug Research, Nankai University, Haihe Education Park, 38 Tongyan Road, Tianjin, 300353, PR China. Electronic address:

N-acetyltransferases are a family of enzymes that catalyze the transfer of the acetyl moiety (COCH) from acetyl coenzyme A (Acetyl-CoA) to a primary amine of acceptor substrates from small molecules such as aminoglycoside to macromolecules of various proteins. In this study, the substrate selectivity of three N-acetyltransferases falling into different phylogenetic groups was probed against a series of hexosamines and synthetic peptides. GlmA from Clostridium acetobutylicum and RmNag from Rhizomucor miehei, which have been defined as glucosamine N-acetyltransferases, were herein demonstrated to be also capable of acetylating the free amino group on the very first glycine residue of peptide in spite of varied catalytic efficiency. Read More

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http://dx.doi.org/10.1016/j.carres.2018.11.011DOI Listing
November 2018
3 Reads

Lewis acid-catalysed nucleophilic opening of a bicyclic hemiaminal followed by ring contraction: Access to functionalized L-idonojirimycin derivatives.

Carbohydr Res 2018 Nov 13;472:65-71. Epub 2018 Nov 13.

Equipe Synthèse Organique - Groupe Glycochimie Institut de Chimie des Milieux et Materiaux de Poitiers (IC2MP), UMR-CNRS 7285, Université de Poitiers, Bâtiment B28, TSA 51106, 4 rue Michel Brunet, 86073, Poitiers cedex 9, France. Electronic address:

The Lewis acid-catalyzed nucleophilic opening of a D-gluco-configured bicyclic hemiaminal has been examined. Several Lewis acids and silylated nucleophiles have been screened allowing the introduction of acetophenone, phosphonate or nitrile at the pseudoanomeric position in satisfactory yields and high 1,2 trans stereoselectivities. Their skeletal rearrangement triggered by the N-benzyl anchimeric assistance provided the corresponding L-ido-configured piperidines displaying various functional groups at C-6 position in good yield. Read More

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http://dx.doi.org/10.1016/j.carres.2018.11.008DOI Listing
November 2018
1 Read

Development of a colorimetric PNGase activity assay.

Carbohydr Res 2018 Nov 16;472:58-64. Epub 2018 Nov 16.

Glycomics and Glycan Bioengineering Research Center (GGBRC), College of Food Science and Technology, Nanjing Agricultural University, 1 Weigang, Nanjing, 210095, China. Electronic address:

PNGases are crucial targets and valuable tools in analyzing asparagine-linked carbohydrate moieties (N-glycans) of glycoproteins. Activity tests of PNGases have been little improved since their discovery four decades ago, and still rely on observing deglycosylation patterns of glycoproteins or glycopeptides using SDS-PAGE or HPLC analysis. These techniques cannot be easily adapted for automated sampling and high-throughput procedures. Read More

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https://linkinghub.elsevier.com/retrieve/pii/S00086215183046
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http://dx.doi.org/10.1016/j.carres.2018.11.007DOI Listing
November 2018
14 Reads
1.929 Impact Factor

A versatile synthesis of αGalCer and its analogues exploiting a cyclic carbonate as phytosphingosine 3,4-diol protecting group.

Carbohydr Res 2018 Nov 15;472:50-57. Epub 2018 Nov 15.

Dipartimento di Scienze del Farmaco, Università del Piemonte Orientale, L. go Donegani 2, 28100, Novara, Italy. Electronic address:

A convenient synthetic strategy to αGalCer and some relevant analogues by using a handily protected phytosphingosine is reported here. The conversion of the phytosphingosine amino group to azide and the protection of 3,4-diol as cyclic carbonate group, cleavable in mild basic conditions but resistant to acidic treatment, afforded quickly an excellent glycosyl acceptor. Its glycosylation with a proper galactosyl donor, gave a versatile intermediate in high yield and excellent stereoselectivity. Read More

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https://linkinghub.elsevier.com/retrieve/pii/S00086215183061
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http://dx.doi.org/10.1016/j.carres.2018.11.005DOI Listing
November 2018
3 Reads

Molecular design of potent, hydrophilic tyrosinase inhibitors based on the natural dihydrooxyresveratrol skeleton.

Carbohydr Res 2018 Nov 13;472:42-49. Epub 2018 Nov 13.

Department of Applied Biological Chemistry, School of Agriculture, Utsunomiya University, Tochigi, 321-0943, Japan. Electronic address:

In this study, dihydrooxyresveratrol glucosides 3-6 were synthesized for the first time to the best of our knowledge by the Wittig reaction and Schmidt glycosylation as key steps for the purpose of developing novel hydrophilic tyrosinase inhibitors. Results obtained from inhibitory studies revealed 50% inhibitory concentration (IC) values of 12.80 μM and 2. Read More

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http://dx.doi.org/10.1016/j.carres.2018.11.006DOI Listing
November 2018
9 Reads

Synthesis of C-β-d-glucopyranosyl derivatives of some fused azoles for the inhibition of glycogen phosphorylase.

Carbohydr Res 2018 Nov 7;472:33-41. Epub 2018 Nov 7.

Department of Organic Chemistry, University of Debrecen, H-4002, Debrecen, POB 400, Hungary. Electronic address:

Annulated C-β-d-glucopyranosyl heterocycles were synthesized and tested as inhibitors of glycogen phosphorylase. 2-(β-d-Glucopyranosyl)-1H-imidazo[4,5-b]pyridine was formed by ring-closure of O-perbenzoylated C-β-d-glucopyranosyl formic acid with 2,3-diaminopyridine in the presence of triphenylphosphite. Cyclisations of bromomethyl 2,3,4,6-tetra-O-benzoyl-β-d-glucopyranosyl ketone with a set of 2-aminoheterocycles resulted in constitutionally reversed C-β-d-glucopyranosyl imidazoles fused by pyridine, pyrimidine, thiazole, 1,3,4-thiadiazole, benzothiazole and benzimidazole. Read More

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http://dx.doi.org/10.1016/j.carres.2018.11.003DOI Listing
November 2018
7 Reads

Synthesis of novel triazole-derived glycopeptides as analogs of α-dystroglycan mucins.

Carbohydr Res 2018 Nov 11;472:23-32. Epub 2018 Nov 11.

Faculty of Pharmaceutical Sciences of Ribeirão Preto - USP, Av. do Café S/N, CEP 14040-903, Ribeirão Preto, SP, Brazil; Barão de Mauá University Centre, 423 Ramos de Azevedo Street, Jardim Paulista, CEP 14090-180, Ribeirão Preto, SP, Brazil. Electronic address:

α-Dystroglycan (α-DG) mucins are essential for maintenance of the structural and functional stability of the muscle fiber and, when hypoglycosylated, they are directly involved in pathological processes such as dystroglycanopathies. Thus, this work reports the synthesis of the novel 1,2,3-triazole-derived glycosyl amino acids αGlcNAc-1-O-triazol-2Manα-ThrOH (1) and Gal-β1,4-αGlcNAc-1-O-triazol-2Manα-ThrOH (2), followed by solid-phase assembly to get the corresponding glycopeptides NHAcThrVal[αGlcNAc-1-triazol-2Manα]ThrIleArgGlyOH (3) and NHAcThrVal[Gal-β1,4-αGlcNAc-1-triazol-2Manα]ThrIleArgGlyOH (4) as analogs of α-DG mucins. The glycosyl amino acids 1 (72%) and 2 (35%) were synthesized by Cu(I)-assisted 1,3-dipolar azide-alkyne cycloaddition reactions (CuAAC) between the azide-glycosyl amino acid αManN-FmocThrOBn (5) and the corresponding alkyne-functionalyzed sugars 2'-propynyl-αGlcNAc (6) and 2'-propynyl-Gal-β1,4-αGlcNAc (7), followed by hydrogenation reactions. Read More

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http://dx.doi.org/10.1016/j.carres.2018.11.004DOI Listing
November 2018
11 Reads

Gold-catalyzed synthesis of α-D-glucosides using an o-ethynylphenyl β-D-1-thioglucoside donor.

Carbohydr Res 2019 Jan 26;471:56-63. Epub 2018 Oct 26.

Department of Chemistry and Biochemistry, University of California, Santa Barbara, Santa Barbara, CA, 93117, United States. Electronic address:

A gold-catalyzed glucosylation method using an o-ethynylphenyl β-D-1-thioglucoside as donor is described. The reaction proceeds in a mostly S2 pathway. A series of α-D-glucosides are obtained in good yields and with up to 19:1 α-selectivity. Read More

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http://dx.doi.org/10.1016/j.carres.2018.10.010DOI Listing
January 2019
5 Reads

Chemoenzymatic radiosynthesis of 2-deoxy-2-[F]fluoro-d-trehalose ([F]-2-FDTre): A PET radioprobe for in vivo tracing of trehalose metabolism.

Carbohydr Res 2018 Nov 4;472:16-22. Epub 2018 Nov 4.

Department of Chemistry and Biochemistry, Central Michigan University, Mount Pleasant, MI, United States. Electronic address:

Trehalose analogues bearing fluorescent and click chemistry tags have been developed as probes of bacterial trehalose metabolism, but these tools have limitations with respect to in vivo imaging applications. Here, we report the radiosynthesis of the F-modified trehalose analogue 2-deoxy-2-[F]fluoro-d-trehalose ([F]-2-FDTre), which in principle can be used in conjunction with positron emission tomography (PET) imaging to allow in vivo imaging of trehalose metabolism in various contexts. A chemoenzymatic method employing the thermophilic TreT enzyme from Thermoproteus tenax was used to rapidly (15-20 min), efficiently (70% radiochemical yield; ≥ 95% radiochemical purity), and reproducibly convert the commercially available radiotracer 2-deoxy-2-[F]fluoro-d-glucose ([F]-2-FDG) into the target radioprobe [F]-2-FDTre in a single step; both manual and automated syntheses were performed with similar results. Read More

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http://dx.doi.org/10.1016/j.carres.2018.11.002DOI Listing
November 2018
7 Reads
1.929 Impact Factor

Enzymatic synthesis of non-natural trisaccharides and galactosides; Insights of their interaction with galectins as a function of their structure.

Carbohydr Res 2018 Nov 3;472:1-15. Epub 2018 Nov 3.

Laboratorio de Bioquímica, Departamento de Biociencias, Facultad de Química, UdelaR, Gral. Flores, 2124, Montevideo, Uruguay. Electronic address:

Galectins are a family of carbohydrate-recognizing proteins that by interacting with specific glycoepitopes can mediate important biological processes, including immune cell homeostasis and activation of tolerogenic circuits. Among the different members of this family, Galectin 1 and 3 have shown pro-tumorigenic effects, being overexpressed in numerous neoplasic diseases, proving to be relevant in tumor immune escape, tumor progression and resistance to drug-induced apoptosis. Thus, generation of specific glycosides that could inhibit their pro-tumorigenic ability by blocking their carbohydrate recognition domain is one of the current major challenges in the field. Read More

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http://dx.doi.org/10.1016/j.carres.2018.10.011DOI Listing
November 2018
9 Reads

Novel glucopyranoside C2-derived 1,2,3-triazoles displaying selective inhibition of O-GlcNAcase (OGA).

Carbohydr Res 2019 Jan 26;471:43-55. Epub 2018 Oct 26.

School of Pharmaceutical Sciences of Ribeirão Preto, University of São Paulo, Av. do Café s/n, Monte Alegre, 14040-930, Ribeirão Preto, Brazil. Electronic address:

O-GlcNAcylation or O-GlcNAc modification is a post-translational modification of several proteins responsible for fundamental cellular processes. Dysregulation of the O-GlcNAc pathway has been linked to the etiology of several diseases such as neurodegenerative and cardiovascular diseases, type 2 diabetes and cancer. O-GlcNAcase (OGA) catalyzes the removal of O-GlcNAc from the modified proteins and several carbohydrate-based OGA inhibitors have been synthesized to understand the role of O-GlcNAc-modified proteins in physiological and pathological conditions. Read More

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http://dx.doi.org/10.1016/j.carres.2018.10.007DOI Listing
January 2019
5 Reads

Synthesis of a biotinylated probe from biotechnologically derived β-d-mannopyranosyl-(1 → 2)-d-mannopyranose for assessment of carbohydrate specificity of antibodies.

Carbohydr Res 2019 Jan 1;471:39-42. Epub 2018 Nov 1.

Laboratory of Glycoconjugate Chemistry, N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Prospect 47, 119991, Moscow, Russia. Electronic address:

The disaccharide β-d-mannopyranosyl-(1 → 2)-d-mannopyranose obtained by chemical cleavage and enzymatic dephosphorylation of biotechnologically available phosphomannan was transformed over six steps into a biotinylated probe suitable for assessment of carbohydrate specificity of antibodies induced by yeast cell wall preparations. Read More

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http://dx.doi.org/10.1016/j.carres.2018.10.013DOI Listing
January 2019

The edible mushroom Albatrellus ovinus contains a α-l-fuco-α-d-galactan, α-d-glucan, a branched (1 → 6)-β-d-glucan and a branched (1 → 3)-β-d-glucan.

Carbohydr Res 2019 Jan 1;471:28-38. Epub 2018 Nov 1.

Department of Biotechnology and Food Science, NTNU Norwegian University of Science and Technology, NOBIPOL, NO-7491, Trondheim, Norway.

Albatrellus ovinus, the sheep polypore, is a large, dense mushroom being rich in cell wall material. Polysaccharides were isolated by sequential extraction, enzymatic treatment and analyzed with respect to monosaccharide composition, glycosidic linkages by methylation and GC-MS as well as NMR spectroscopy. A fucogalactan composed of an (1 → 6)-α-d-galactan backbone with single α-l-Fucp residues attached at O-2 was identified in the hot water extract obtained after treatment with a protease and size exclusion chromatography. Read More

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http://dx.doi.org/10.1016/j.carres.2018.10.012DOI Listing
January 2019
4 Reads

Improved synthesis of the Kijanimicin oligodeoxytetrasaccharide.

Carbohydr Res 2019 Jan 1;471:19-27. Epub 2018 Nov 1.

University of Hamburg, Faculty of Science, Department of Chemistry, Martin-Luther-King-Platz 6, D-20146, Hamburg, Germany.

By sequential synthesis the four 2,6-dideoxy saccharide moieties of the kijanimicin tetrasaccharide could be stereoselectively assembled. For formation of all required 2-deoxy α-glycoside linkages various S-(hexopyranosyl)-phosphorodithioates as donor structures could be convincingly employed. The terminal 2-deoxy β-glycoside linkage was stereoselectively formed following the dibromomethyl methyl ether approach. Read More

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http://dx.doi.org/10.1016/j.carres.2018.10.014DOI Listing
January 2019

Structural determination of ananatoside A: An unprecedented 15-membered macrodilactone-containing glycolipid from Pantoea ananatis.

Carbohydr Res 2019 Jan 28;471:13-18. Epub 2018 Oct 28.

INRS - Institut Armand-Frappier, Université du Québec, 531, boul. des Prairies, Laval, Québec, H7V 1B7, Canada. Electronic address:

The bacterium Pantoea ananatis was reported to produce glycolipid biosurfactants of unknown structures. Herein, we present the isolation and structural determination of ananatoside A, the main congener of a new family of 15-membered macrodilactone-containing glucolipids. The structure of ananatoside A was elucidated via chemical degradation and spectroscopic methods including 1D/2D NMR analysis, tandem MS/MS, GC-MS, HR-ESI-TOF-MS, MALDI-TOF-MS, and polarimetry. Read More

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http://dx.doi.org/10.1016/j.carres.2018.10.009DOI Listing
January 2019

Binding silver to chitooligosaccharides through N-heterocyclic carbenes: Synthesis and antimicrobial activity.

Carbohydr Res 2019 Jan 26;471:6-12. Epub 2018 Oct 26.

Instituto de Química del Sur (INQUISUR), Departamento de Química, Universidad Nacional del Sur (UNS)-CONICET, Av. Alem 1253, B8000CPB, Bahía Blanca, Argentina. Electronic address:

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http://dx.doi.org/10.1016/j.carres.2018.10.008DOI Listing
January 2019
3 Reads

One-pot synthesis of glycosyl phenylthiosulfonates from sulfinate, S and glycosyl bromides.

Carbohydr Res 2019 Jan 19;471:1-5. Epub 2018 Oct 19.

Pharmacy School, Jiangsu University, Xuefu Road 301, Zhenjiang City, Jiangsu, 212013, China. Electronic address:

Glycosyl phenylthiosulfonates are reagents which are valuable for the S-glycosylation decoration of organic compounds and proteins. Here, one-pot multiple-component synthesis of glycosyl phenylthiosulfonates from sulfinate, sulfur powder and glycosyl bromides is reported. The reactions afford glycosyl phenylthiosulfonates in good yields under mild conditions. Read More

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http://dx.doi.org/10.1016/j.carres.2018.10.005DOI Listing
January 2019
1 Read

Structural characterization of glucosylated GOS derivatives synthesized by the Lactobacillus reuteri GtfA and Gtf180 glucansucrase enzymes.

Carbohydr Res 2018 Dec 22;470:57-63. Epub 2018 Oct 22.

Microbial Physiology, Groningen Biomolecular Sciences and Biotechnology Institute (GBB), University of Groningen, Nijenborgh 7, 9747 AG, Groningen, the Netherlands.

β-Galacto-oligosaccharides (GOS) are used commercially in infant nutrition, aiming to functionally replace human milk oligosaccharides (hMOS). Glucansucrases Gtf180-ΔN and GtfA-ΔN of Lactobacillus reuteri strains convert sucrose into α-glucans with (α1→6)/(α1→3) and (α1→4)/(α1→6) glucosidic linkages, respectively. Previously we reported that both glucansucrases glucosylate lactose, producing a minimum of 5 compounds (degree of polymerization 3-4) (GL34 mixture) with (α1→2/3/4) linkages. Read More

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http://dx.doi.org/10.1016/j.carres.2018.10.003DOI Listing
December 2018
6 Reads
1.930 Impact Factor

Glycosylation pathways of human corneal and conjunctival epithelial cell mucins.

Carbohydr Res 2018 Dec 20;470:50-56. Epub 2018 Oct 20.

Schepens Eye Research Institute of Massachusetts Eye and Ear, Department of Ophthalmology, Harvard Medical School, Boston, MA, United States.

Mucin glycoproteins on the ocular surface are rich in O-glycans and have important roles in the protection from physical, chemical and microbial impact. In this work, we have cultured human corneal and conjunctival epithelial cells to examine the glycosyltransferase activities that synthesize the O-glycans of mucins. The results indicate that ocular surface epithelial cells have active enzymes that synthesize O-glycans with sialylated core 1, Galβ1-3GalNAcα, and core 2, GlcNAcβ1-6(Galβ1-3)GalNAcα structures which corresponds to previous structural studies. Read More

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http://dx.doi.org/10.1016/j.carres.2018.10.004DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC6311131PMC
December 2018
1 Read

Dehydrative glycosidations of 2-deoxysugar derivatives catalyzed by an arylboronic ester.

Carbohydr Res 2018 Dec 15;470:42-49. Epub 2018 Oct 15.

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

An N-methylpyridinium-4-boronic ester acts as a catalyst for dehydrative glycosidations of 2-deoxy sugar-derived hemiacetals. The catalytic protocol is tolerant of functionalized acceptors, including alcohols bearing isopropylidene ketal, tert-butyl carbamate or benzyl carbamate groups. The results demonstrate that organoboron-catalyzed substitution reactions of alcohols, which have previously been conducted on π-activated (benzylic, allylic or propargylic) substrates, can also be used to achieve C-O bond formation from carbohydrate-derived hemiacetals. Read More

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http://dx.doi.org/10.1016/j.carres.2018.10.002DOI Listing
December 2018

The alginate lyase from Isoptericola halotolerans CGMCC 5336 as a new tool for the production of alginate oligosaccharides with guluronic acid as reducing end.

Carbohydr Res 2018 Dec 12;470:36-41. Epub 2018 Jul 12.

National Engineering Laboratory for Cereal Fermentation Technology, Jiangnan University, 1800 Lihu Avenue, Wuxi, 214122, PR China; School of Biotechnology, Jiangnan University, 1800 Lihu Avenue, Wuxi, 214122, PR China.

Alginate oligosaccharides are depolymerization products of alginate by enzymatic degradation or physicochemical treatments. Alginate lyase has received great interests due to its use in oligosaccharide preparation. The substrate specificity of alginate lyase directly determines the type and degree of polymerization of alginate oligosaccharides. Read More

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http://dx.doi.org/10.1016/j.carres.2018.06.005DOI Listing
December 2018
5 Reads

The use of the novel glycosyl acceptor and supramer analysis in the synthesis of sialyl-α(2-3)-galactose building block.

Carbohydr Res 2018 Dec 9;470:27-35. Epub 2018 Oct 9.

N. D. Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences, Leninsky Prosp., 47, 119991, Moscow, Russian Federation. Electronic address:

A new glycosyl acceptor to be used in sialylation was designed as a 3-hydroxy derivative of 4-methoxyphenyl β-d-galactopyranoside with 2-O-acetyl group and O-4 and O-6 protected as benzylidene acetal. Two alternative syntheses of this compound were compared. Sialylation of 3-OH group of the glycosyl acceptor with O-chloroacetylated N-trifluoroacetylneuraminic acid phenyl thioglycoside (NIS, TfOH, MeCN, MS 3 Å, -40 °C) was studied in a wide concentration range (5-150 mmol L). Read More

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http://dx.doi.org/10.1016/j.carres.2018.10.001DOI Listing
December 2018
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Corrigendum to "Synthesis of glyceryl glycosides related to A-type prymnesin toxins" Carbohydr. Res. 463 (2018) 14-23.

Carbohydr Res 2018 Dec 9;470:26. Epub 2018 Oct 9.

Department of Biological Chemistry, John Innes Centre, Norwich Research Park, Norwich, NR4 7UH, UK. Electronic address:

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http://dx.doi.org/10.1016/j.carres.2018.09.004DOI Listing
December 2018

Selectivity of original C-hexopyranosyl calix[4]arene conjugates towards lectins of different origin.

Carbohydr Res 2018 Nov 21;469:60-72. Epub 2018 Aug 21.

Department of Chemistry of Natural Compounds, University of Chemistry and Technology, Technická 5, 166 28, Prague, Czech Republic.

As a part of ongoing activities towards the design of ligands against pathogenic lectins, a synthesis of original α-C-galacto/α-C-manno/α-C-fucopyranosyl glycomimetics based on a calix[4]arene scaffold and their binding evaluation is described. The interactions of the glycomimetics with seven lectins of various origins were carried out using agglutination inhibition assays. The 1,3-alternate tetra-C-fucosylated ligand and its derivative having a tertBu group at the upper rim of the calix[4]arene scaffold were the most potent towards the AAL lectin family (RSL, AFL, AAL, AOL) and BC2L-C. Read More

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http://dx.doi.org/10.1016/j.carres.2018.08.012DOI Listing
November 2018
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Structure of a lytic polysaccharide monooxygenase from Aspergillus fumigatus and an engineered thermostable variant.

Carbohydr Res 2018 Nov 14;469:55-59. Epub 2018 Aug 14.

Novozymes Inc, 1445 Drew Ave, CA, 95618, Davis, United States.

Lytic polysaccharide monooxygenases (LPMOs) are industrial enzymes which are gaining use in second generation bioethanol production from lignocellulose by acting in synergy with glycoside hydrolases. Here we present the X-ray crystal structure of an AA9 fungal LPMO from Aspergillus fumigatus and a variant which has been shown to have better performance at elevated temperatures. Based on the structures, thermal denaturation data and theoretical calculations, we provide a suggestion for the structural basis of the improved stability. Read More

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https://linkinghub.elsevier.com/retrieve/pii/S00086215183022
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http://dx.doi.org/10.1016/j.carres.2018.08.009DOI Listing
November 2018
18 Reads