10,190 results match your criteria Carbohydrate research[Journal]


Mass spectrometry-based identification of carbohydrate anomeric configuration to determine the mechanism of glycoside hydrolases.

Carbohydr Res 2019 Mar 14;476:53-59. Epub 2019 Mar 14.

Institute of Atomic and Molecular Sciences, Academia Sinica, P. O. Box 23-166, Taipei, 10617, Taiwan; Department of Chemistry, National Tsing Hua University, Hsinchu, 30013, Taiwan. Electronic address:

A rapid mass spectrometry method for determining the anomeric configuration of the sugar at the reducing end of an oligosaccharide was demonstrated. The method was employed to identify the nascent anomeric configuration (i.e. Read More

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http://dx.doi.org/10.1016/j.carres.2019.03.004DOI Listing

Isolation and characterization of a high molecular mass β-glucan from Lactobacillus fermentum Lf2 and evaluation of its immunomodulatory activity.

Carbohydr Res 2019 Mar 9;476:44-52. Epub 2019 Mar 9.

Department of Chemical Sciences, University of Huddersfield, Queensgate, Huddersfield, HD1 3DH, United Kingdom. Electronic address:

When grown in a semi-defined medium, L. fermentum Lf2 synthesizes significant quantities (∼2 g/L) of two exopolysaccharides (EPS). The two EPS were separated by preparative size exclusion chromatography to give a high molecular mass β-glucan (1. Read More

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http://dx.doi.org/10.1016/j.carres.2019.03.003DOI Listing

A metal free mild and green approach for tandem opening of 4,6-O-benzylidene acetals to their corresponding 6-O-acetyl derivatives: Application in the synthesis of a trisaccharide using one-pot glycosylation reactions.

Carbohydr Res 2019 Mar 14;476:36-43. Epub 2019 Mar 14.

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

An efficient and high yielding reaction for tandem opening of 4,6-O-benzylidene derivatives (gluco, galacto, manno, 2-phthalimido-2-deoxy glucosides) to their corresponding 6-O-acetyl derivatives has been established under metal free condition using 60% solution of aqueous acetic acid (v/v). The reaction is equally pertinent for large scale synthesis and also for disaccharide glycosides. Its application for the construction of a building block towards synthesis of a trisaccharide part related to Pseudomonas aeruginosa utilizing one-pot glycosylation reactions has also been described. Read More

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http://dx.doi.org/10.1016/j.carres.2019.03.002DOI Listing

Advances in chemical modifications of starches and their applications.

Carbohydr Res 2019 Mar 2;476:12-35. Epub 2019 Mar 2.

State Key Laboratory of Chemical Engineering, College of Chemical and Biological Engineering, Zhejiang University, Hangzhou, 310027, People's Republic of China.

Starch is a homopolysaccharide made up of glucose units which are linked together via a glycosidic linkage. This biopolymer is well known for its low cost, biodegradability, renewability and easy availability. In spite of all these beauties, starch has some problems with their solubility in water, retrogradation, loss of viscosity due to rupturing of glucosidic bond when subjected to treatment and absence of some groups of primary importance like different functional groups especially carboxylic group, ester group, ether group and amino group. Read More

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http://dx.doi.org/10.1016/j.carres.2019.02.007DOI Listing

Total synthesis of scutellarin and apigenin 7-O-β-d-glucuronide.

Carbohydr Res 2019 Feb 19;475:69-73. Epub 2019 Feb 19.

The National Research Center for Carbohydrate Synthesis, Jiangxi Normal University, 99 Ziyang Avenue, Nanchang 330022, China. Electronic address:

A general protocol for direct glucuronic linkages formation featuring Au(I)-catalyzed appropriately protected glucuronyl o-alkynylbenzoate-involved glycosylation reaction, as well as a concise approach for easy access of scutellarein prominent for the mild and efficient hydroxyl group installation via borylation-oxidation sequence from flavanone derivative, has been established, based on which a novel route for scutellarin derivatives preparation has been devised. The developed strategies, among which the stepwise deprotection process was also included, guarantee the high whole synthetic efficiency, and definitely will find broad application in diversity-oriented synthesis of bioactive flavonoid glycosides. Read More

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http://dx.doi.org/10.1016/j.carres.2019.02.005DOI Listing
February 2019

Structural analysis of holothurian fucosylated chondroitin sulfates: Degradation versus non-destructive approach.

Carbohydr Res 2019 Mar 1;476:8-11. Epub 2019 Mar 1.

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

Fucosylated chondroitin sulfates (FCS) are unique glycosaminoglycans isolated from the body walls of sea cucumbers (holothuria). These biopolymers are composed of a chondroitin core [→4)-β-d-GlcA-(1 → 3)-β-d-GalNAc-(1→] bearing fucosyl branches and the sulfate groups. Fucosyl substituents prevent enzymatic degradations of FCS by chondroitinases, which are effectively used in the structural analysis of vertebrate chondroitin sulfates, and hence, several non-enzymatic approaches to structural elucidation of FCS have been developed. Read More

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http://dx.doi.org/10.1016/j.carres.2019.02.008DOI Listing

Chemical synthesis of the 4-amino-4,6-dideoxy-d-glucose containing pentasaccharide repeating unit of the O-specific polysaccharide from Aeromonas hydrophila strain K691 in the form of its 2-aminoethyl glycoside.

Carbohydr Res 2019 Mar 5;476:1-7. Epub 2019 Mar 5.

Sweet Lab, Department of Chemical Sciences, Indian Institute of Science Education and Research (IISER) Kolkata, Mohanpur, Nadia, 741246, India. Electronic address:

Chemical synthesis of the pentasaccharide repeating unit of the O-specific polysaccharide from Aeromonas hydrophilastrain K691 is reported. Synthesis of the pentasaccharide is accomplished by using a common disaccharide in sequence and finally attaching the rare sugar unit. The target structure was made in the form of its 2-aminoethyl glycoside which is essential for further glycconjugate formation. Read More

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http://dx.doi.org/10.1016/j.carres.2019.02.009DOI Listing

New lectin ligands: Testing of Amadori rearrangement products with a series of mannoside-specific lectins.

Carbohydr Res 2019 Feb 19;475:65-68. Epub 2019 Feb 19.

Glycogroup, Institute of Organic Chemistry, Graz University of Technology, Stremayrgasse 9, A-8010, Graz, Austria. Electronic address:

1-(N-Phenyl)amino-1-deoxy-α-D-manno-hept-2-ulose (2) and two multivalent BSA-based structures 7 and 8, d-manno-configured C-glycosyl-type compounds derived from an Amadori rearrangement, were evaluated as ligands for mannoside-specific lectins of various sources. The determination of the concentration corresponding to 50% of inhibition (IC) is described. Multivalency turned out to effectively influence ligand selectivity and lectin binding. Read More

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http://dx.doi.org/10.1016/j.carres.2019.01.010DOI Listing
February 2019

Effect of modified di- and trisaccharides on hyaluronidase activity assessed by capillary electrophoresis-based enzymatic assay.

Carbohydr Res 2019 Feb 23;475:56-64. Epub 2019 Feb 23.

Institut de Chimie Organique et Analytique, Université d'Orléans, CNRS FR 2708, UMR 7311, Orléans, France. Electronic address:

The activity of eukaryote hydrolase-type of hyaluronidases was studied using a miniaturized capillary electrophoresis (CE) assay developed in our laboratory. Few nanoliters of reagents are sufficient and no labeling is required for this assay. The effect of natural and original synthetic effectors of hyaluronidase was evaluated. Read More

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http://dx.doi.org/10.1016/j.carres.2019.02.006DOI Listing
February 2019
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1.929 Impact Factor

Synthesis of di- and trihydroxy proline derivatives from D-glycals: Application in the synthesis of polysubstituted pyrrolizidines and bioactive 1C-aryl/alkyl pyrrolidines.

Carbohydr Res 2019 Feb 20;475:48-55. Epub 2019 Feb 20.

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

Six different types of O-benzyl protected proline derivatives have been synthesized from D-glycals and 2C-formyl-glycals. One of the di-O-benzyl protected proline derivatives has been utilized for the synthesis of polysubstituted pyrrolizidines via [3 + 2] cycloaddition in a stereoselective manner. Further, we also report on the stereoselective synthesis of biologically active 1C-aryl/alkyl pyrrolidines i. Read More

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http://dx.doi.org/10.1016/j.carres.2019.02.004DOI Listing
February 2019
1.929 Impact Factor

Impact of branching on the conformational heterogeneity of the lipopolysaccharide from Klebsiella pneumoniae: Implications for vaccine design.

Carbohydr Res 2019 Feb 18;475:39-47. Epub 2019 Feb 18.

University of Maryland Computer-Aided Drug Design Center, Department of Pharmaceutical Sciences, School of Pharmacy, University of Maryland, Baltimore, MD, 21201, United States. Electronic address:

Resistance of Klebsiella pneumoniae (KP) to antibiotics has motivated the development of an efficacious KP human vaccine that would not be subject to antibiotic resistance. Klebsiella lipopolysaccharide (LPS) associated O polysaccharide (OPS) types have provoked broad interest as a vaccine antigen as there are only 4 that predominate worldwide (O1, O2a, O3, O5). Klebsiella O1 and O2 OPS are polygalactans that share a common D-Gal-I structure, for which a variant D-Gal-III was recently discovered. Read More

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http://dx.doi.org/10.1016/j.carres.2019.02.003DOI Listing
February 2019
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On the effect of intramolecular H-bonding in the configurational assessment of polyhydroxylated compounds with computational methods. The hyacinthacines case.

Carbohydr Res 2019 Feb 28;474:72-79. Epub 2019 Jan 28.

Instituto de Química de Rosario, Facultad de Ciencias Bioquímicas y Farmacéuticas, Universidad Nacional de Rosario - CONICET, Suipacha 531, S2002LRK, Rosario, Argentina. Electronic address:

Hyacinthacines are important members of the pyrrolizidine family, with several compounds having ambiguous, revised or unverified structures. Herein we thoroughly explored the performance DP4 and DP4+ for the in silico stereoassignment of hyacinthacines A1, A2 and five synthetic isomers. The results suggested that the quality of the predictions strongly depended on the conformational landscape provided by DFT energies, with five compounds correctly assigned. Read More

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http://dx.doi.org/10.1016/j.carres.2019.01.011DOI Listing
February 2019
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Hydrolysis and interactions of d-cellobiose with polycarboxylic acids.

Carbohydr Res 2019 Feb 12;475:34-38. Epub 2019 Feb 12.

Department of Chemistry, Prairie View A&M University, Prairie View, TX, 77446, USA.

The hydrolysis of cellulose model compound d-cellobiose was studied with a series of eight common polycarboxylic acids and two monocarboxylic acids in aqueous medium using 0.500 mmol -COOH/L at 170 °C. The maleic acid showed the highest catalytic activity with turnover frequency (TOF) of 29. Read More

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http://dx.doi.org/10.1016/j.carres.2019.02.002DOI Listing
February 2019

Structural investigation of α-l-fucosidase from the pancreas of Patiria pectinifera, based on molecular cloning.

Carbohydr Res 2019 Feb 7;475:27-33. Epub 2019 Feb 7.

Department of Applied Chemistry and Biochemistry, National Institute of Technology, Fukushima College, 30 Nagao, Iwaki, Fukushima, 970-8034, Japan. Electronic address:

An α-l-fucosidase (Pap-Alf) was purified from the pancreas of a starfish Patiria pectinifera by ammonium sulfate precipitation followed by several column chromatographies. The molecular mass of the purified enzyme was estimated to be 52.6 kDa by SDS-PAGE, although gel filtration analysis of the native enzyme suggests it exists as a homodimer in solution. Read More

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http://dx.doi.org/10.1016/j.carres.2019.02.001DOI Listing
February 2019
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Probing deoxysugar conformational preference: A comprehensive computational study investigating the effects of deoxygenation.

Carbohydr Res 2018 Dec 12;475:17-26. Epub 2018 Dec 12.

Department of Chemistry, Indiana University, Bloomington, IN, 47405, USA. Electronic address:

Deoxysugars are intrinsic components in a number of antibiotics, antimicrobials, and therapeutic agents that often dictate receptor binding, improve efficacy, and provide a diverse toolbox in modifying glycoconjugate function due to an extensive number of unique isomers and inherent conformational flexibility. Hence, this work provides a comprehensive examination of the conformational effects associated with deoxygenation of the pyranose ring. Both the location and degree of deoxygenation were evaluated by interrogating the energetic landscape for a number of mono- and dideoxyhexopyranose derivatives using DFT methods (M05-2X/cc-pVTZ(-f)). Read More

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http://dx.doi.org/10.1016/j.carres.2018.12.003DOI Listing
December 2018

Development of a novel nanoprobe from alginate functionlized gold nanoparticles and 3-(dansylamino)phenylboronic acid for glucose detection and enhanced 4-nitrophenol reduction.

Carbohydr Res 2019 Feb 7;475:11-16. Epub 2019 Feb 7.

Department of Environmental Engineering, North China Institute of Science and Technology, PO Box 206, Yanjiao, Beijing, 101601, PR China. Electronic address:

Gold nanoparticles (AuNPs) were prepared by a solvothermal method using sodium alginate (SA) as both, the reductant and stabilizer. The formation of SA-AuNPs was confirmed by UV-Vis spectroscopy, transmission electron microscopy, X-ray diffractometry, and X-ray photoelectron spectroscopy. SA-AuNPs were functionalized with fluorescent 3-(dansylamino)phenylboronic acid (DAPB) moieties, through interactions between boronic acids and diol groups. Read More

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http://dx.doi.org/10.1016/j.carres.2019.01.014DOI Listing
February 2019

Structure elucidation and gene cluster characterization of the O-antigen of Vibrio cholerae O14.

Carbohydr Res 2019 Feb 21;474:67-71. Epub 2019 Jan 21.

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

The O-polysaccharide (O-antigen) of Vibrio cholerae O14 was studied using chemical analyses and 1D and 2D NMR spectroscopy. The following structure of the repeating unit of the O-antigen was established: where GlcpN(SHb) indicates 2-deoxy-2-[(S)-3-hydroxybutanoylamino]-d-glucose. We found that Vibrio cholerae O14 is similar to that of O-polysaccharide of Azospirillum brasilense S17, which has been reported earlier. Read More

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https://linkinghub.elsevier.com/retrieve/pii/S00086215183057
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http://dx.doi.org/10.1016/j.carres.2019.01.007DOI Listing
February 2019
3 Reads

Characterization of the 6-O-acetylated lipoglucuronomannogalactan a novel Cryptococcus neoformans cell wall polysaccharide.

Carbohydr Res 2019 Jan 29;475:1-10. Epub 2019 Jan 29.

Laboratório de Glicobiologia, Instituto de Biofísica Carlos Chagas Filho, Universidade Federal do Rio de Janeiro, Rio de Janeiro, 21942-902, Brazil. Electronic address:

Glucuronoxylomannogalactans (GXMGals) are characteristic capsular polysaccharides produced by the opportunistic fungus C. neoformans, which are implicated in cryptococcal virulence, via impairment of the host immune response. We determined for the first time the structure of a lipoglucuronomannogalactan (LGMGal), isolated from the surface of a mutant C. Read More

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http://dx.doi.org/10.1016/j.carres.2019.01.012DOI Listing
January 2019
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N-glycans in Toxicodendron vernicifluum lacquer laccase.

Carbohydr Res 2019 Feb 14;474:57-66. Epub 2019 Jan 14.

Department of Bio and Environmental Chemistry, Kitami Institute of Technology, 165 Koen-cho, Kitami, Hokkaido, 090-8507, Japan. Electronic address:

The N-glycans in Toxicodendron vernicifluum (Rhus vernicifera) lacquer laccase was elucidated for the first time through a combination of enzymatic digestion and subsequent mass spectrometry measurements using LC-MS/MS and MALDI-TOF MS. Lacquer laccase was isolated from a Japanese lacquer acetone powder from consecutive Sephadex C-50 and DEAE A-50 column chromatography. Trypsin and chymotrypsin digestions of the lacquer laccase resulted in a mixture of peptides and N-glycopeptides, which were treated with peptide-N-glycosidases and then N-(aminooxyacetyl)tryptophanylarginine methyl ester (aoWR) to give the aoWR-labelled N-glycans. Read More

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http://dx.doi.org/10.1016/j.carres.2018.12.001DOI Listing
February 2019
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Stereoselective trimethylsilylation of α- and β-galactopyranoses.

Carbohydr Res 2019 Feb 30;474:51-56. Epub 2019 Jan 30.

Graduate School of Engineering, Tokai University, 4-1-1 Kitakaname, Hiratsuka, Kanagawa, 259-1292, Japan; Department of Applied Biochemistry, Tokai University, 4-1-1 Kitakaname, Hiratsuka, Kanagawa, 259-1292, Japan. Electronic address:

Trimethylsilylation of the anomeric hydroxyl groups of tetra-O-benzyl and tetra-O-acetyl galactopyranoses was investigated. Stereoselective formation of β-trimethylsilyl glycoside (β-TMS glycoside) of benzyl protected compound was achieved using N-trimethylsilyl diethylamine. In the course of the investigation of the selective synthesis of TMS galactosides using TMS-imidazole, we observed the formation of an intermediate, which was converted predominantly into α-TMS glycoside after silica gel column chromatography. Read More

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http://dx.doi.org/10.1016/j.carres.2019.01.013DOI Listing
February 2019

Synthesis of neuraminidase-resistant sialoside-modified three-way junction DNA and its binding ability to various influenza viruses.

Carbohydr Res 2019 Feb 21;474:43-50. Epub 2019 Jan 21.

Graduate School of Human Development and Environment, Kobe University, 3-11 Tsurukabuto, Kobe, Hyogo 657-8501, Japan. Electronic address:

Natural sialic acid-modified compounds are capable of targeting influenza virus hemagglutinin (HA). However, these compounds have limited inhibitory effect because natural O-glycoside bond in these compounds are prone to be cleaved by neuraminidase (NA) on the surface of viruses. In this study, we synthesized NA-resistant sialoside that included unnatural S-glycoside bonds and modified this sialoside on a three-way junction (3WJ) DNA to display complementary distribution to its binding sites on a HA trimer. Read More

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http://dx.doi.org/10.1016/j.carres.2019.01.008DOI Listing
February 2019

A versatile de novo synthesis of legionaminic acid and 4-epi-legionaminic acid starting from d-serine.

Carbohydr Res 2019 Feb 23;474:34-42. Epub 2019 Jan 23.

AG Schmid, Institute of Organic Chemistry, University of Vienna, Währinger Straße 38, A-1090, Vienna, Austria.

Legionaminic acid and 4-epi-legionaminic acid are 5,7-diacetamido nonulosonic acids and are assumed to play a crucial role in the virulence of Legionella pneumophila, the causative agent of Legionnaires' disease. Moreover, they are ideal target motifs for the development of vaccines and pathogen detection. Herein, we present a versatile de novo synthesis of legionaminic acid and 4-epi-legionaminic acid. Read More

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https://linkinghub.elsevier.com/retrieve/pii/S00086215183073
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http://dx.doi.org/10.1016/j.carres.2019.01.009DOI Listing
February 2019
5 Reads

Ligand-controlled, transition-metal catalyzed site-selective modification of glycosides.

Carbohydr Res 2019 Feb 22;474:16-33. Epub 2019 Jan 22.

Department of Emergency, State Key Laboratory of Biotherapy and Cancer Center, West China Hospital and School of Chemical Engineering, Sichuan University, No. 17 Renmin Nan Road, Chengdu, 610041, China. Electronic address:

Carbohydrates play important roles in many physiological and pathological events. The preparation of the derivatives and conjugates of carbohydrates is often needed to help interrogate and exploit their biological properties. Owning to their structural complexity, one major challenge in the derivatization of carbohydrates is to control site-selectivity, that is, to selectively modify one hydroxyl group in the presence of many others. Read More

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http://dx.doi.org/10.1016/j.carres.2019.01.006DOI Listing
February 2019

ADP-heptose: A new innate immune modulator.

Carbohydr Res 2019 Feb 19;473:123-128. Epub 2018 Dec 19.

Department of Chemistry, Georgia State University, Atlanta, GA, 30303, USA. Electronic address:

Lipopolysaccharide (LPS) is a well-known pathogen-associated molecular pattern (PAMP) produced by gram-negative bacteria. Previous studies showed that a key metabolic intermediate in LPS biosynthesis, d-glycero-β-d-manno-heptose 1,7-bisphosphate (HBP), could activate the NF-κB pathway and trigger the innate immune responses. However, it was unclear whether HBP could be a novel PAMP and its pattern recognition receptor (PRR) is not fully understood. Read More

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http://dx.doi.org/10.1016/j.carres.2018.12.011DOI Listing
February 2019

A unique structural distribution pattern discovered for the cerebrosides from starfish Asterias amurensis.

Carbohydr Res 2019 Feb 24;473:115-122. Epub 2018 Dec 24.

Department of Applied Biochemistry, Tokai University, 4-1-1 Kitakaname, Hiratsuka, Kanagawa, 259-1292, Japan. Electronic address:

Cerebroside is an important family of the mono-glycosylated ceramides involved in the larger family of glycosphingolipid and sulfatide. Cerebroside is synthesized from ceramide by the transfer of glucose from UDP-glucose, and degraded back to ceramide, which plays an important role at the epidermis protecting interior of the body as a barrier. Because cerebroside is regarded as the source molecule of ceramide and is amphiphilic in nature, cerebroside is considered valuable as the ingredient of cosmetic lotion. Read More

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http://dx.doi.org/10.1016/j.carres.2018.12.013DOI Listing
February 2019

Tautomeric and epimeric equilibria of aldo- and ketohexoses studied by the MD simulations and QM calculations.

Carbohydr Res 2019 Feb 11;474:8-15. Epub 2019 Jan 11.

Jerzy Haber Institute of Catalysis and Surface Chemistry, Polish Academy of Sciences, ul. Niezapominajek 8, 30-239, Cracow, Poland. Electronic address:

The article is devoted to the problem of molecular modeling of tautomeric and epimeric equilibria in aqueous solutions of unfunctionalized d-aldo- and d-ketohexoses. We have applied the computational protocol proposed in our previous article [Gaweda, Plazinski, Phys. Chem. Read More

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http://dx.doi.org/10.1016/j.carres.2019.01.004DOI Listing
February 2019
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Characterization of CBM36-containing GH11 endoxylanase NtSymX11 from the hindgut metagenome of higher termite Nasutitermes takasagoensis displaying prominent catalytic activity.

Carbohydr Res 2019 Feb 11;474:1-7. Epub 2019 Jan 11.

Department of Biotechnology, The University of Tokyo, 1-1-1 Yayoi, Bunkyo-ku, Tokyo, 113-8657, Japan. Electronic address:

Symbionts in the gut of termites are expected to be large sources of enzymes involved in lignocellulose degradation, but their biotechnological potential has not been fully explored. In this study, we expressed, purified, and biochemically characterized a glycoside hydrolase family 11 xylanase, NtSymX11, from a symbiotic bacterium of the higher termite, Nasutitermes takasagoensis. NtSymX11 is a multimodular enzyme consisting of a catalytic domain and two tandem carbohydrate-binding modules (CBM36). Read More

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http://dx.doi.org/10.1016/j.carres.2019.01.003DOI Listing
February 2019
3 Reads

Chemo-enzymatic synthesis of p-nitrophenyl β-D-galactofuranosyl disaccharides from Aspergillus sp. fungal-type galactomannan.

Carbohydr Res 2019 Feb 11;473:99-103. Epub 2019 Jan 11.

Graduate School of Environmental and Life Science, Okayama University, Tsushima-naka 1-1-1, Okayama, 700-8530, Japan. Electronic address:

β-d-Galactofuranose (Galf) is a component of polysaccharides and glycoconjugates. There are few reports about the involvement of galactofuranosyltransferases and galactofuranosidases (Galf-ases) in the synthesis and degradation of galactofuranose-containing glycans. The cell walls of filamentous fungi in the genus Aspergillus include galactofuranose-containing polysaccharides and glycoconjugates, such as O-glycans, N-glycans, and fungal-type galactomannan, which are important for cell wall integrity. Read More

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https://linkinghub.elsevier.com/retrieve/pii/S00086215183073
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http://dx.doi.org/10.1016/j.carres.2019.01.005DOI Listing
February 2019
6 Reads

Structural analysis of a novel lipooligosaccharide (LOS) from Rhodobacter azotoformans.

Carbohydr Res 2019 Feb 7;473:104-114. Epub 2019 Jan 7.

Department of Applied Biochemistry, Tokai University, 4-1-1 Kitakaname, Hiratsuka, Kanagawa, 259-1292, Japan. Electronic address:

Lipopolysaccharides (LPS) are components of the Gram-negative bacterial cell surface that stimulate the host innate immune system through the Toll-like receptor (TLR) 4-MD-2 complex. Rhodobacter sp. have been reported to produce LPS that lack endotoxic activity, and instead act as antagonists of other endotoxins. Read More

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https://linkinghub.elsevier.com/retrieve/pii/S00086215183068
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http://dx.doi.org/10.1016/j.carres.2018.12.018DOI Listing
February 2019
7 Reads

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 Feb 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
February 2019
1 Read

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

Carbohydr Res 2019 Feb 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
February 2019
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Recent advances in reagent-controlled stereoselective/stereospecific glycosylation.

Carbohydr Res 2019 Feb 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
February 2019
10 Reads

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

Carbohydr Res 2019 Feb 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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https://linkinghub.elsevier.com/retrieve/pii/S00086215183049
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http://dx.doi.org/10.1016/j.carres.2019.01.001DOI Listing
February 2019
8 Reads

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

Carbohydr Res 2019 Feb 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
February 2019
1 Read
1.929 Impact Factor

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

Carbohydr Res 2019 Feb 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
February 2019
5 Reads
1.929 Impact Factor

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 2019 Feb 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
February 2019
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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 2019 Feb 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
February 2019
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Synthesis of a hexasaccharide repeating unit of the cell wall polysaccharide of Bifidobacterium animalis subsp. lactis LKM512.

Carbohydr Res 2019 Feb 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
February 2019
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Structures of cell-wall glycopolymers of Lactobacillus rhamnosus BIM B-1039.

Carbohydr Res 2019 Jan 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
January 2019
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The characterisation of a galactokinase from Streptomyces coelicolor.

Carbohydr Res 2019 Jan 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
January 2019
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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 2019 Feb 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
February 2019
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Structure of the O-specific polysaccharide from a halophilic bacterium Halomonas ventosae RU5S2EL.

Carbohydr Res 2019 Feb 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
February 2019
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Substrate binding versus escape dynamics in a pH-affected fungal beta-glucosidase revealed by molecular dynamics simulations.

Carbohydr Res 2019 Jan 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
January 2019
3 Reads
1.929 Impact Factor

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

Carbohydr Res 2019 Jan 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
January 2019
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Facile chemoenzymatic synthesis of Lewis a (Le) antigen in gram-scale and sialyl Lewis a (sLe) antigens containing diverse sialic acid forms.

Carbohydr Res 2019 Jan 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
January 2019
11 Reads

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

Carbohydr Res 2019 Jan 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
January 2019
2 Reads

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

Carbohydr Res 2019 Jan 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
January 2019
3 Reads

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
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Strategies for chemoenzymatic synthesis of carbohydrates.

Carbohydr Res 2019 Jan 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
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC6342554PMC
January 2019
2 Reads

Stereoselective synthesis and antiproliferative activity of the isomeric sphinganine analogues.

Carbohydr Res 2019 Jan 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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https://linkinghub.elsevier.com/retrieve/pii/S00086215183052
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http://dx.doi.org/10.1016/j.carres.2018.09.008DOI Listing
January 2019
3 Reads