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Accueil > Les équipes > Glycochimie Organique Biologique et Supramoléculaire (GOBS) > Publications

Publications

publié le , mis à jour le

2014


  • B. Riflade, D. Lachkar, J. Oble, J. Li, S. Thorimbert, B. Hasenknopf, et E. Lacôte, « Pd-Containing Organopolyoxometalates Derived from Dawson Polyoxometalate [P2W15V3O62](9-): Lewis Acidity and Dual Site Catalysis », Organic Letters, vol. 16, nᵒ 15, p. 3860-3863, 2014.
    Résumé : Grafting of a palladium complex to the Dawson vanadotungstate polyanion [P2W15V3O62](9-) via an organic ligand generates a large family of pincer-type hybrid polyoxometalates. The palladium-POM derivatives have dual catalytic properties. Unlike their parent inorganic polyanions, they catalyze allylations while retaining their oxidant character, which leads to single-pot dual site catalysis. This opens a new route for multicatalytic reactions.
    Mots-clés : Allylation, bond, CHEMBIO, complex, cyclization, Functionalization, GOBS, hybrid, oxygenation, Palladium, POLE 1, POLE 3, polyoxotungstate, spectroscopic characterization.

  • M. - P. Santoni, G. S. Hanan, et B. Hasenknopf, « Covalent multi-component systems of polyoxometalates and metal complexes: Toward multi-functional organic-inorganic hybrids in molecular and material sciences », Coordination Chemistry Reviews, vol. 281, p. 64-85, déc. 2014.
    Résumé : The rational design and synthesis of organic-inorganic hybrids in molecular and material sciences lies at the interface of several domains, such as synthetic organic and inorganic chemistry, coordination chemistry and supramolecular chemistry. Efforts to develop these hybrids focus not only on the structural features of the materials, but also on their applications in catalysis, photochemistry, magnetism and medicine. Adequate functionalization of polyoxometalates allows to further complex transition metals leading to multi-component systems that feature the combined intrinsic properties of each component as well as new properties originating from the combination of these components. We will discuss the synthesis and characterization of both molecular and polymeric hybrids, and their potential applications in catalysis, material science and energy-related sciences. (C) 2014 Elsevier B.V. All rights reserved.
    Mots-clés : Coordination chemistry, Coordination complexes and polymers, electron-transfer reactions, GOBS, keggin-type polyoxometalate, langmuir-blodgett-films, magnetic clusters, Multi-functional molecular materials, Organic-inorganic hybrids, Photoactivity, photoelectrochemical cells, photophysical properties, POLE 3, Polyoxometalates, structural-characterization, supramolecular triangles, Synthetic design, thin-films.

  • M. - P. Santoni, A. K. Pal, D. Chartrand, G. S. Hanan, P. Menard-Tremblay, M. - C. Tang, K. Venne, A. Furtos, et B. Hasenknopf, « Palladium(II)-Directed Self-Assembly of a Neutral Molecular Triangle as a Heteroditopic Receptor for Ion Pairs », Inorganic Chemistry, vol. 53, nᵒ 19, p. 10039-10041, oct. 2014.
    Résumé : A molecular triangle, based on the self-assembly of 4,7-phenanthroline by a neutral palladium complex, has been synthesized and characterized by a combination of techniques: H-1 NMR and UV-vis absorption spectroscopies, mass spectrometry, elemental analysis, and gel permeation chromatography. This new neutral metallocavitand has demonstrated the capacity to host both anionic and cationic guests, thus acting as an open-shaped heteroditopic receptor. Density functional theory calculations have shown that (i) there is no overtension in the assembly of the discrete triangle, which is more stable than open-chain oligomers, (ii) the adducts formed between the triangle and some salts (modeled in the gas phase) are thermodynamically stable, and (iii) two types of cavities coexist in the triangle, which host ions and ion pairs. This easily accessible triangular unit extends further the rational design of model nanoarchitectures in host guest chemistry with applications in analytical chemistry and multifunctional molecular materials.
    Mots-clés : 4,7-phenanthroline, anion receptors, complexes, Coordination chemistry, design, GOBS, Metallacycles, metallatriangles, POLE 3, recognition, square, supramolecular triangles.

  • M. - P. Santoni, A. K. Pal, G. S. Hanan, M. - C. Tang, A. Furtos, et B. Hasenknopf, « A light-harvesting polyoxometalate-polypyridine hybrid induces electron transfer as its Re(I) complex dagger », Dalton Transactions, vol. 43, nᵒ 19, p. 6990-6993, 2014.
    Résumé : A derivative of the Dawson polyoxometalate [P2V3W15O62](9)-functionalized with one remote bipyridine coordination site (2) has been synthesized and combined with the neutral {Re(CO)(3)Br} moiety. The new Re-I-hybrid (3) was characterized by various analytical techniques. Hybrid 3 exhibits several redox processes on a wide range of potentials with reductions centered on V(V), W(VI) and the organic ligand in order of decreasing potential. Both units, the polyoxometalate and the transition metal complex, retain their intrinsic properties in the hybrid 3, which displays photosensitization in the UV region with tailing into high-energy visible region.
    Mots-clés : co2, coordination-compounds, GOBS, hydrogen evolution, lysine, organic-compounds, POLE 3, polyoxotungstate, redox derivatives, reduction, visible-light, water.

  • L. Shen, N. Xie, B. Yang, Y. Hu, et Y. Zhang, « Design and total synthesis of Mannich derivatives of marine natural product lamellarin D as cytotoxic agents », European Journal of Medicinal Chemistry, vol. 85, p. 807-817, oct. 2014.
    Résumé : Enlightened by the modification route from Camptothecin (CPT) to Topotecan and based on classical drug design theory, a series of Mannich derivatives of lamellarin D were designed and synthesized in 26-27 steps starting from vanillin and isovanilin. All synthesized compounds were then biologically evaluated for their in vitro anti-cancer activities and Topo I inhibitory activities. The results showed that most target compounds exhibited Topo I inhibitory activities in equivalent level with that of lamellarin D. Compound SL-9 exhibited better Topo I inhibitory activity than that of lamellarin D. Compounds SL-2, SL-3, SL-4, SL-5 and SL-11 exhibited better anti-proliferative activity against HT-29 cells than that of lamellarin D. (C) 2014 Elsevier Masson SAS. All rights reserved.
    Mots-clés : Alkaloids, alpha 20-sulfate, Anti-cancer, camptothecin, cellular internalization, Derivative, GOBS, hiv-1 integrase, Inhibitor, Lamellarin D, Mannich, POLE 3, Structure-activity relationships, substitution, Topo I, topoisomerase-i, unnatural lamellarins, vitro.
  • M. Sollogoub, Y. Bleriot, G. Prencipe, et N. Auberger, « Imino-Sugar C-Glycosides, Preparation and Use Thereof », U.S. Patent EP2734534, Extension CA2842015, US20140296288, WO2013011098, WO20130110982014.


  • D. N. Tran, D. Colesnic, S. Adam de Beaumais, G. Pembouong, F. Portier, Á. A. Queijo, J. Vázquez Tato, Y. Zhang, M. Ménand, L. Bouteiller, et M. Sollogoub, « Cyclodextrin-adamantane conjugates, self-inclusion and aggregation versus supramolecular polymer formation », Organic Chemistry Frontiers, vol. 1, nᵒ 6, p. 703, 2014.

  • S. Xiao, Q. Wang, L. Si, Y. Shi, H. Wang, F. Yu, Y. Zhang, Y. Li, Y. Zheng, C. Zhang, C. Wang, L. Zhang, et D. Zhou, « Synthesis and Anti- HCV Entry Activity Studies of bCyclodextrin- Pentacyclic Triterpene Conjugates », ChemMedChem, vol. 9, nᵒ 5, p. 1060-1070, mai 2014.
    Résumé : In our previous studies, oleanolic acid (OA) and echinocystic acid (EA), isolated from Dipsacus asperoides, were found to have anti-HCV entry properties. The major issue for members of this type of triterpene is their low water solubility. In this study, a series of new water-soluble triazole-bridged -cyclodextrin (CD)-pentacyclic triterpene conjugates were synthesized via click chemistry. Thanks to the attached -CD moiety, all synthesized conjugates showed lower hydrophobicity (AlogP) than their parent compounds. Several conjugates exhibited moderate anti-HCV entry activity. With the exception of per-O-methylated -CD-pentacyclic triterpene conjugates, all other conjugates showed no cytotoxicity based on an alamarBlue assay carried out with HeLa, HepG2, MDCK, and 293T cells. More interestingly, the hemolytic activity of these conjugates disappeared upon the introduction of -CDs. Easy access to such conjugates that combine the properties of -CD and pentacyclic triterpenes may provide a way to obtain a new class of anti-HCV entry inhibitors.
    Mots-clés : aids agents, antiviral agents, betulinic acid, click chemistry, crataegus-sinaica, cyclodextrins, derivatives, echinocystic acid, GOBS, HCV entry inhibitors, hiv activity, inhibitors, moronic acid, oleanolic acid, pentacyclic triterpenes, POLE 3, virus.

  • B. Xu, L. Unione, J. Sardinha, S. Wu, M. Etheve-Quelquejeu, A. Pilar Rauter, Y. Bleriot, Y. Zhang, S. Martin-Santamaria, D. Diaz, J. Jimenez-Barbero, et M. Sollogoub, « gem-Difluorocarbadisaccharides: Restoring the exo-Anomeric Effect. », Angewandte Chemie International Edition, vol. 53, nᵒ 36, p. 9597-602, juill. 2014.
    Résumé : Molecular mimicry is an essential part of the development of drugs and molecular probes. In the chemical glycobiology field, although many glycomimetics have been developed in the past years, it has been considered that many failures in their use are related to the lack of the anomeric effects in these analogues. Additionally, the origin of the anomeric effects is still the subject of virulent scientific debates. Herein, by combining chemical synthesis, NMR methods, and theoretical calculations, we show that it is possible to restore the anomeric effect for an acetal when replacing one of the oxygen atoms by a CF2 group. This result provides key findings in chemical sciences. On the one hand, it strongly suggests the key relevance of the stereoelectronic component of the anomeric effect. On the other hand, the CF2 analogue adopts the natural glycoside conformation, which might provide new avenues for sugar-based drug design. 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
    M

    ots-clés :
    GOBS, POLE 3.


  • W. - J. Xuan, C. Botuha, B. Hasenknopf, et S. Thorimbert, « Addition of carbon nucleophiles to hemiaminals promoted by a Lewis acidic polyoxotungstate », Organic Chemistry Frontiers, vol. 1, nᵒ 9, p. 1091-1095, sept. 2014.
    Mots-clés : CHEMBIO, GOBS, POLE 3.
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  • Y. - Y. Zhao, S. - P. Wu, S. Liu, Y. Zhang, et R. - C. Lin, « Ultra-performance liquid chromatography–mass spectrometry as a sensitive and powerful technology in lipidomic applications », Chemico-Biological Interactions, vol. 220, p. 181-192, 2014.

  • M. Zhong, Y. Zhang, et X. He, « Synthesis and Anticonvulsant Activity of Ethyl 2,2-dimethyl-1-(2-substitutedhydrazinecarboxamido) Cyclopropanecarboxylate Derivatives », Chemical Biology & Drug Design, vol. 84, nᵒ 2, p. 234-241, août 2014.
    Résumé : In this study on the development of new anticonvulsants, fourteen ethyl 2,2-dimethyl-1-(2-substitutedhydrazinecarboxamido) cyclopropanecarboxylate derivatives were synthesized and tested for anticonvulsant activity using the maximal electroshock, subcutaneous pentylenetetrazole screens, which are the most widely employed seizure models for early identification of candidate anticonvulsants. Their neurotoxicity was determined applying the rotorod test. Two compounds 6f and 6k showed promising anticonvulsant activities in both models employed for anticonvulsant evaluation. The most active compound 6k showed the maximal electroshock-induced seizures with ED50 value of 9.2 mg/kg and TD50 value of 387.5 mg/kg after intraperitoneally injection to mice, which provided compound 6k with a protective index (TD50/ED50) of 42.1 in the maximal electroshock test.
    Mots-clés : acids, anticonvulsant activity, antiepileptic drugs, discovery, epilepsy, Ethyl 2,2-dimethyl-1-(2-substitutedhydrazinecarboxamido) cyclopropanecarboxylate, GOBS, MES test, POLE 3, scPTZ test, thioureas.

  • Y. Zhou, H. - Y. Zhao, K. - L. Han, Y. Yang, B. - B. Song, Q. - N. Guo, Z. - C. Fan, Y. - M. Zhang, Y. - O. Teng, et P. Yu, « 5-(2-Carboxyethenyl) isatin derivative induces G(2)/M cell cycle arrest and apoptosis in human leukemia K562 cells », Biochemical and Biophysical Research Communications, vol. 450, nᵒ 4, p. 1650-1655, août 2014.
    Résumé : Our previous study successfully identified that the novel isatin derivative (E)-methyl 3-(1-(4-methoxy-benzyl)-2,3-dioxoindolin-5-yl) acrylate (HKL 2H) acts as an anticancer agent at an inhibitory concentration (IC50) level of 3 nM. In this study, the molecular mechanism how HKL 2H induces cytotoxic activity in the human chronic myelogenous leukemia K562 cells was investigated. Flow cytometric analysis showed that the cells were arrested in the G(2)/M phase and accumulated subsequently in the sub-G(1) phase in the presence of HKL 2H. HKL 2H treatment down-regulated the expressions of CDK1 and cyclin B but up-regulated the level of phosphorylated CDK1. Annexin-V staining and the classic DNA ladder studies showed that HKL 2H induced the apoptosis of K562 cells. Our study further showed that HKL 2H treatment caused the dissipation of mitochondrial membrane potential, activated caspase-3 and lowered the Bcl-2/Bax ratio in K562 cells, suggesting that the HKL 2H-causing programmed cell death of K562 cells was caused via the mitochondrial apoptotic pathway. Taken together, our data demonstrated that HKL 2H, a 5-(2-carboxyethenyl) isatin derivative, notably induces G(2)/M cell cycle arrest and mitochondrial-mediated apoptosis in K562 cells, indicating that this compound could be a promising anticancer candidate for further investigation. (C) 2014 Elsevier Inc. All rights reserved.
    Mots-clés : anticancer agents, Apoptosis, caspase-3 inhibitors, Cell cycle, GOBS, Isatin derivatives, mitochondria, POLE 3, su11248, sulfonamide analogs, vitro cytotoxicity evaluation.

  • Z. - Y. Zhu, W. Pang, Y. - Y. Li, X. - R. Ge, L. - J. Chen, X. - C. Liu, Q. Lv, G. - L. Dong, A. - J. Liu, et Y. Zhang, « Effect of ultrasonic treatment on structure and antitumor activity of mycelial polysaccharides from Cordyceps gunnii », Carbohydrate Polymers, vol. 114, p. 12-20, déc. 2014.
    Résumé : Taking mycelial polysaccharides from Cordyceps gunnii (C. gunnii) as the study subject, the effect of ultrasonic power, time and concentration of polysaccharides on antitumor activity of the polysaccharides was investigated. The ultrasonic processing condition of the polysaccharides was optimized by using orthogonal test design, and determined to be 400 W, 15 min and 1 g/L. The change of structures of polysaccharides before and after ultrasonic treatment was also studied. Results show that ultrasonic treatment did not change the characteristic attribute of polysaccharides from C gunnii. The composition of monosaccharide residues and the category of glycosidic bond have not been changed. But the molecular weight and intrinsic viscosity was reduced, and the alpha-helicity was enhanced after ultrasonic treatment. It was possible that ultrasonic treatment is an effective way for enhancing antitumor activity of polysaccharides. (C) 2014 Elsevier Ltd. All rights reserved.
    Mots-clés : C. gunnii, GOBS, Mycelial polysaccharide, POLE 3, structure, sugars, Ultrasonic, Antitumor activity.

  • Z. - Y. Zhu, W. - X. Wang, Z. -qian Wang, L. - J. Chen, J. - Y. Zhang, X. -cui Liu, S. -ping Wu, et Y. -min Zhang, « Synthesis and antitumor activity evaluation of chrysin derivatives », European Journal of Medicinal Chemistry, vol. 75, p. 297-300, mars 2014.
    Résumé : A series of 5,7-disubstituted chrysin, 7-monosubstituted chrysin, 5-monosubstituted chrysin derivatives were synthesized by alkylation, acetylation, benzoylation, carboxymethylation, and evaluated on their antitumor activity of H22 cells in the search for potential antitumor agents. Among them, compound 3 (5,7-diacetyl chrysin) displayed the most potent antitumor activity with IC50 value of 141 mu M. Moreover, there is significant up-regulation of G2 in cell cycle of H22. (C) 2014 Elsevier Masson SAS. All rights reserved.
    Mots-clés : Active sites, Antitumor agents, Chrysin derivatives, complex, GOBS, h22, Inhibition of cell division, POLE 3.

  • Z. - Y. Zhu, J. - Y. Zhang, L. - J. Chen, X. - C. Liu, Y. Liu, W. - X. Wang, et Y. - M. Zhang, « Comparative evaluation of polysaccharides isolated from Astragalus, oyster mushroom, and yacon as inhibitors of alpha-glucosidase », Chinese Journal of Natural Medicines, vol. 12, nᵒ 4, p. 290-293, avr. 2014.
    Résumé : The incidence of diabetes has increased considerably, and become the third serious chronic disease following cancer and cardiovascular diseases. Though acarbose, metformin, and 1-deoxynojirimycin have good efficacy for clinical application as hypoglycemic drugs, their expensive costs and some degree of side effects have limited their clinical application. Recently, increasing attention has concentrated on the polysaccharides from natural plant and animal sources for diabetes. In order to illustrate the pharmaceutical activity of polysaccharides as natural hypoglycemic agents, polysaccharides isolated from Astragalus, oyster mushroom, and Yacon were evaluated for their inhibitory effects on alpha-glucosidase. Polysaccharides were extracted and purified from Astragalus, Oyster mushroom, and Yacon with hot water at 90 degrees C for 3 h, respectively. The total sugar content of the polysaccharide was determined by the phenol-sulfuric acid method. The alpha-glucosidase inhibitory activity was measured by the glucose oxidase method. The results exhibited that the inhibitory effects on alpha-glucosidase were in decreasing order, Astragalus > oyster mushroom > Yacon. The alpha-glucosidase inhibition percentage of Astragalus polysaccharide and oyster mushroom polysaccharide were over 40% at the polysaccharide concentration of 0.4 mg.mL(-1). The IC50 of Astragalus polysaccharide and oyster mushroom polysaccharide were 0.28 and 0.424 mg.mL(-1), respectively. The information obtained from this work is beneficial for the use polysaccharides as a dietary supplement for health foods and therapeutics for diabetes.
    Mots-clés : alpha-Glucosidase, Astragalus, Diabetes, entamoeba-histolytica, GOBS, Inhibition activity, Oyster mushroom, Yacon, POLE 3, Polysaccharide, purification.

2013


  • M. Fonvielle, D. Mellal, D. Patin, M. Lecerf, D. Blanot, A. Bouhss, M. Santarem, D. Mengin-Lecreulx, M. Sollogoub, M. Arthur, et M. Etheve-Quelquejeu, « Efficient Access to Peptidyl-RNA Conjugates for Picomolar Inhibition of Non-ribosomal FemXWv Aminoacyl Transferase », Chemistry-a European Journal, vol. 19, nᵒ 4, p. 1357-1363, janv. 2013.
    Résumé : PeptidylRNA conjugates have various applications in studying the ribosome and enzymes participating in tRNA-dependent pathways such as Fem transferases in peptidoglycan synthesis. Herein a convergent synthesis of peptidylRNAs based on HuisgenSharpless cycloaddition for the final ligation step is developed. Azides and alkynes are introduced into tRNA and UDP-MurNAc-pentapeptide, respectively. Synthesis of 2'-azido RNA helix starts from 2'-azido-2'-deoxyadenosine that is coupled to deoxycytidine by phosphoramidite chemistry. The resulting dinucleotide is deprotected and ligated to a 22-nt RNA helix mimicking the acceptor arm of Ala-tRNAAla by T4 RNA ligase. For alkyne UDP-MurNAc-pentapeptide, meso-cystine is enzymatically incorporated into the peptidoglycan precursor and reduced, and L-Cys is converted to dehydroalanine with O-(mesitylenesulfonyl)hydroxylamine. Reaction of but-3-yne-1-thiol with dehydroalanine affords the alkyne-containing UDP-MurNAc-pentapeptide. The CuI-catalyzed azide alkyne cycloaddition reaction in the presence of tris[(1-hydroxypropyl-1H-1,2,3-triazol-4-yl)methyl]amine provided the peptidyl-RNA conjugate, which was tested as an inhibitor of non-ribosomal FemXWv aminoacyl transferase. The bi-substrate analogue was found to inhibit FemXWv with an IC50 of (89+/-9) pM, as both moieties of the peptidylRNA conjugate contribute to high-affinity binding.
    Mots-clés : alanyl, biosynthesis, cell-wall synthesis, click chemistry, escherichia-coli, GOBS, inhibitors, ligase murm, ligation, mimics, peptidoglycan, peptidyl-RNA conjugates, POLE 3, rna, streptococcus-pneumoniae, transferases, udp-murnac-pentapeptide.


  • S. Guieu et M. Sollogoub, « Advances in Cyclodextrin Chemistry », in Modern Synthetic Methods in Carbohydrate Chemistry, D. B. Werz et S. Vidal, Éd. Wiley-VCH Verlag GmbH & Co. KGaA, 2013, p. 241-283.
    Résumé : Cyclodextrins are a class of cyclic oligomers composed of glucopyranosidic units in the 4C1 conformation, linked in an α-1,4 manner (Figure 48). They were isolated by Villiers [1] in 1891, but their structure was elucidated only in 1942 [2]. They are obtained by enzymatic degradation of starch, using cyclodextrin glucosyltransferase (CGTase), as a mixture of α-cyclodextrin 1, β-cyclodextrin 2, and γ-cyclodextrin 3, possessing six, seven, or eight glucosides, respectively, and other oligomers [3]. Industrially, they are separated by selective precipitation in yields ranging from 40 to 60%.
    Mots-clés : bulky protecting groups, capping reagents, cyclodextrins, differentiation, diisobutylaluminum hydride, Functionalization, GOBS, POLE 3, regioselective deprotections, regioselective protections, regioselectivity, selectivity.


  • M. Guitet, F. Marcelo, S. A. de Beaumais, Y. Zhang, J. Jiménez-Barbero, S. Tilloy, E. Monflier, M. Ménand, et M. Sollogoub, « Diametrically Opposed Carbenes on an α-Cyclodextrin: Synthesis, Characterization of Organometallic Complexes and Suzuki–Miyaura Coupling in Ethanol and in Water », European Journal of Organic Chemistry, vol. 2013, nᵒ 18, p. 3691–3699, 2013.
    Résumé : Two carbene-based ligands have been attached to perbenzylated and permethylated cyclodextrins. Their palladium complexes were synthesized, characterized and used as catalysts in Suzuki–Miyaura coupling reactions both in ethanol and water.
    Mots-clés : Carbene ligands, cyclodextrins, GOBS, homogeneous catalysis, nitrogen heterocycles, Palladium, POLE 3.


  • M. Guitet, P. Zhang, F. Marcelo, C. Tugny, J. Jiménez-Barbero, O. Buriez, C. Amatore, V. Mouriès-Mansuy, J. - P. Goddard, L. Fensterbank, Y. Zhang, S. Roland, M. Ménand, et M. Sollogoub, « NHC-Capped Cyclodextrins (ICyDs): Insulated Metal Complexes, Commutable Multicoordination Sphere, and Cavity-Dependent Catalysis », Angewandte Chemie International Edition, vol. 52, nᵒ 28, p. 7213–7218, 2013.
    Mots-clés : cavitands, COS, cyclodextrins, Electrochemistry, GOBS, homogeneous catalysis, MACO, N-heterocyclic carbenes, POLE 1, POLE 3.


  • J. D. Howe, N. Smith, M. J. - R. Lee, N. Ardes-Guisot, B. Vauzeilles, J. Désiré, A. Baron, Y. Blériot, M. Sollogoub, D. S. Alonzi, et T. D. Butters, « Novel imino sugar α-glucosidase inhibitors as antiviral compounds », Bioorganic & Medicinal Chemistry, vol. 21, nᵒ 16, p. 4831-4838, 2013.
    Résumé : Abstract Deoxynojirimycin (DNJ) based imino sugars display antiviral activity in the tissue culture surrogate model of Hepatitis C (HCV), bovine viral diarrhoea virus (BVDV), mediated by inhibition of ER α-glucosidases. Here, the antiviral activities of neoglycoconjugates derived from deoxynojirimycin, and a novel compound derived from deoxygalactonojirimycin, by click chemistry with functionalised adamantanes are presented. Their antiviral potency, in terms of both viral infectivity and virion secretion, with respect to their effect on α-glucosidase inhibition, are reported. The distinct correlation between the ability of long alkyl chain derivatives to inhibit ER α-glucosidases and their anti-viral effect is demonstrated. Increasing alkyl linker length between DNJ and triazole groups increases α-glucosidase inhibition and reduces the production of viral progeny RNA and the maturation of the envelope polypeptide. Disruption to viral glycoprotein processing, with increased glucosylation on BVDV E2 species, is representative of α-glucosidase inhibition, whilst derivatives with longer alkyl linkers also show a further decrease in infectivity of secreted virions, an effect proposed to be distinct from α-glucosidase inhibition.
    Mots-clés : Bovine viral diarrhea virus, Endoplasmic reticulum, Glucosidases, GOBS, Imino sugars, Neoglycoconjugates, POLE 3.


  • U. Jacquemard, P. Harpainter, et S. Roland, « Introduction of bulky tert-butyl substituents on the core of N,N′-diaryl N-heterocyclic carbenes through the corresponding vicinal diamines », Tetrahedron Letters, vol. 54, nᵒ 35, p. 4793-4795, 2013.
    Résumé : Abstract Highly bulky N,N′-diaryl imidazolinium salts substituted by one or two tert-butyl groups on the heterocyclic backbone and the corresponding silver N-heterocyclic carbene complexes are obtained by the addition of tert-butyl magnesium chloride or tert-butyl lithium on symmetrical 1,2-bisimines derived from 2,6-diisopropylaniline, 2,6-diethylaniline and 2,4,6-trimethylaniline.
    Mots-clés : Carbene ligands, Chiral ligands, GOBS, Imidazoliniums, POLE 3, Silver complexes, Vicinal diamines.


  • I. k Ahmed, R. Farha, Z. Huo, C. Allain, X. Wang, H. Xu, M. Goldmann, B. Hasenknopf, et L. Ruhlmann, « Porphyrin–polyoxometalate hybrids connected via a Tris-alkoxo linker for the generation of photocurrent », Electrochimica Acta, vol. 110, p. 726-734, 2013.


  • E. Leclerc, X. Pannecoucke, M. Ethève-Quelquejeu, et M. Sollogoub, « Fluoro-C-glycosides and fluoro-carbasugars, hydrolytically stable and synthetically challenging glycomimetics », Chemical Society Reviews, vol. 42, nᵒ 10, p. 4270-4283, avr. 2013.
    Résumé : Fluoro-C-glycosides and fluoro-carbasugars are a particular subclass of hydrolytically stable glycomimetics that are expected to have different, hopefully improved properties thanks to the stereoelectronic features of the fluoroalkyl moiety. This review summarizes the studies devoted to the synthesis of such Carbohydrate chemistry
    Mots-clés : GOBS, POLE 3.

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  • J. Liang, J. He, S. Zhu, W. Zhao, Y. Zhang, Y. Ito, et W. Sun, « Preparation of Main Iridoid Glycosides in Fructus Corni by Macroporous Resin Column Chromatography and Countercurrent Chromatography », Journal of Liquid Chromatography & Related Technologies, vol. 36, nᵒ 8, p. 983-999, mars 2013.
    Résumé : Loganin, sweroside, and morroniside, three main iridoid glycosides from Fructus Corni were successfully separated by macroporous resin column chromatography and countercurrent chromatography (CCC). In the first step, D101 macroporous resin was selected for cleaning-up, water was used to elute the column to remove the undesired constituents and then 50% aqueous ethanol was used to elute the targets. The total content of three iridoid glycosides was 51.1% in this process. In the second step, the obtained crude sample was then isolated by CCC using a two-phase solvent system composed of dichloromethane-methanol-n-butanol-water-acetic acid (5:5:2:4:0.1, v/v/v/v/v). From 100mg of a crude sample, 12.6mg of loganin, 5.9mg of sweroside, and 28.5mg of morroniside were obtained with purities of 98.6%, 97.3%, and 99.1% and total recoveries of 90.4%, 91.8%, and 89.1%, respectively, after a two-step purification. The HPLC quantitative analysis and response surface methodology were used for optimization of the separation condition and the target compounds were identified by ESI-MS, 1H NMR, and 13C NMR.
    Mots-clés : cells, constituents, countercurrent chromatography, Fructus Corni, GOBS, hsccc, inflammation, loganin, macroporous resin column chromatography, mice, morroniside, officinalis, POLE 3, purification, scopolamine, sweroside.

  • X. Ling, N. Schaeffer, S. Roland, et M. - P. Pileni, « Nanocrystals: Why Do Silver and Gold N-Heterocyclic Carbene Precursors Behave Differently? », Langmuir, vol. 29, nᵒ 41, p. 12647-12656, oct. 2013.
    Résumé : Synthesizing stable Au and Ag nanocrystals of narrow size distribution from metal-N-heterocyclic carbene (NHC) complexes remains a challenge, particularly in the case of Ag and when NHC ligands with no surfactant-like properties are used. The formation of nanocrystals by one-phase reduction of metal-NHCs (metal = Au, Ag) bearing common NHC ligands, namely 1,3-diethylbenzimidazol-2-ylidene.(L-1), 1,3-bis(mesityl)imidazol-2-ylidene (L-2), and 1,3-bis(2,6-(Pr2C6H3)-Pr-i)imidazol-2-ylidene (L-3), is presented herein. We show that both Au and Ag nanocrystals displaying narrow size distribution can be formed by reduction with amine boranes. The efficiency of the process and the average size and size distribution of the nanocrystals markedly depend on the nature of the metal and NHC ligand, on the sequence in the reactant addition (i.e., presence or absence of thiol during the reduction step), and on the presence or absence of oxygen. Dodecanethiol was introduced to produce stable nanocrystals associated with narrow size distributions. A specific reaction is observed with Ag NHCs in the presence of thiols whereas Au-NHCs remain unchanged. Therefore, different organometallic species are involved in the reduction step to produce the seeds. This can be correlated to the lack of effect of NHCs on Ag nanocrystal size. In contrast, alteration of Au nanocrystal average size can be achieved with a NHC ligand of great steric bulk (L-3). This demonstrates that a well-defined route for a given metal cannot be extended to another metal.
    Mots-clés : catalysis, chemistry, complexes, GOBS, Heterocycles, layered structure, metal nanoparticles, nucleation, phase synthesis, POLE 3, size, solid-state, system.


  • K. Micoine, M. Malacria, E. Lacôte, S. Thorimbert, et B. Hasenknopf, « Regioselective Double Organic Functionalization of Polyoxotungstates through Electrophilic Addition of Aromatic Isocyanates to [P2W17O61(SnR)]7– », European Journal of Inorganic Chemistry, vol. 2013, nᵒ 10-11, p. 1737–1741, 2013.
    Résumé : The direct attachment of several different organic molecules to a single polyoxometalate remains a challenge in the field of functionalized polyoxometalates. In this paper, we show that an organotin-functionalized Dawson-type polyoxotungstate [P2W17O61(SnR)]7– reacts with aromatic isocyanates ArNCO to yield new doubly functionalized compounds [P2W17O61(SnR)(CONHAr)]6–. Both organic moieties, Ar and R, can be varied independently; we have tested nine Ar and three R groups. Therefore, this synthetic methodology represents a way to graft two distinct functional molecules directly onto a polyoxometalate.
    Mots-clés : CHEMBIO, COS, Electrophilic addition, GOBS, Heterocycles, MACO, organic–inorganic hybrid composites, POLE 1, POLE 3, Polyoxometalates, SUPRA, synthesis design, Tungsten.


  • B. Riflade, J. Oble, L. Chenneberg, E. Derat, B. Hasenknopf, E. Lacôte, et S. Thorimbert, « Hybrid polyoxometalate palladacycles: DFT study and application to the Heck reaction », Tetrahedron, vol. 69, nᵒ 27–28, p. 5772-5779, 2013.
    Résumé : The phosphovanadotungstate polyanion [P2W15V3O62]9− is a powerful support to stabilize palladacycles conjugated to the inorganic framework via an organic ligand. The insertion can be directed toward sp2 or sp3 C–H insertion upon appropriate choice of the substitution pattern on the organic ligand. DFT modeling indicates that the strong withdrawing effect of the POM transmitted through the conjugated carbonyl was responsible for this easy insertion. The palladacycles led to the formation of stilbene via a Mizoroki–Heck reaction. However it is likely that the POMs act as Pd-reservoirs for the formation of nanoparticles.
    Mots-clés : catalysis, CHEMBIO, COS, C–H insertion, GOBS, Heck reaction, Heterocycles, Hybrid polyoxometalate, MACO, Palladacycles, POLE 1, POLE 3, SSO, SUPRA.


  • C. s Allain, D. Schaming, N. Karakostas, M. Erard, J. - P. Gisselbrecht, S. Sorgues, I. Lampre, L. Ruhlmann, et B. Hasenknopf, « Synthesis, electrochemical and photophysical properties of covalently linked porphyrin–polyoxometalates », Dalton Transactions, vol. 42, nᵒ 8, p. 2745-2754, janv. 2013.
    Résumé : Two covalently linked porphyrin–polyoxometalate hybrids have been prepared: an Anderson-type hexamolybdate [N(C4H9)4]3[MnMo6O18{(OCH2)3CNHCO(ZnTPP)}2] with two pendant zinc(ii)-tetraphenylporphyrins, and a Dawson-type vanadotungstate [N(C4H9)4]5H[P2V3W15O59{(OCH2)3CNHCO(ZnTPP)}] with one porphyrin. Electroch
    Mots-clés : GOBS, POLE 3, SUPRA.

  • M. - P. Santoni, F. Nastasi, S. Campagna, G. S. Hanan, B. Hasenknopf, et I. Ciofini, « Understanding the redox properties of dinuclear ruthenium(II) complexes by a joint experimental and theoretical analysis », Dalton Transactions, vol. 42, nᵒ 15, p. 5281-5291, 2013.
    Résumé : A combined experimental and theoretical approach has been used to investigate the redox properties of two dinuclear Ru(II) complexes, 2a and 2b, containing the planar dpt-ph-dpt bridging ligand (dpt-ph-dpt = 1 '', 4 ''-bis(2,4-dipyrid-2'-yl-1,3,5-triazin-6-yl) benzene). The redox properties of the free bridging ligand and the X-ray structure of 2a have also been reported, together with the X-ray structure of a related mononuclear compound, for comparison purposes. The photophysical processes of 2a and 2b have also been studied by pump-probe transient absorption spectroscopy. Compounds 2a and 2b are able to reversibly collect six and eight electrons, respectively, upon electrochemical reduction at mild potentials (>-2.0 V vs. SCE). A detailed assignment of the various reduction processes to specific subunits of the dinuclear arrays has been made possible by calculation of the HOMOs and LUMOs of native and bireduced species. For example, computation allowed us to clarify the redox behavior of 2b: the first reduction processes of this compound occur at almost coincident potentials, with successive electrons added on the same subunit (namely, the bridging ligand). Charge redistribution towards the other subunits of the molecular framework upon second reduction, revealed by calculation performed on the bireduced species, is the key to interpreting this peculiar behavior. Inter-ligand electron hopping interconverts the MLCT state involving the peripheral ligand to that of the (lower-lying) MLCT state that involves the bridging ligand. This process is faster than 350 fs in 2a, where its driving force is higher than 0.2 eV, whereas it occurs with a time constant of about 6 ps in 2b, having a smaller driving force for the process. Both compounds decay to the ground state, with MLCT emission on the nanosecond time scale, however a faster component of such decay is kinetically evidenced, indicating a process of about 200-250 ps in both cases, which is tentatively assigned to relatively slow diffusive solvent dynamics.
    Mots-clés : absorption-spectra, artificial photosynthesis, electrochemical oxidation, electron-transfer, energy-gap law, GOBS, photocatalytic hydrogen-production, photophysical properties, POLE 3, SUPRA, transfer excited-states, transition-metal-complexes, tridentate ligands.


  • M. Sollogoub, « Site-Selective Heterofunctionalization of Cyclodextrins: Discovery, Development, and Use in Catalysis », Synlett, vol. 24, nᵒ 20, p. 2629-2640, oct. 2013.


  • S. Xiao, M. Yang, F. Yu, L. Zhang, D. Zhou, P. Sinaÿ, et Y. Zhang, « Synthesis of four mono-functionalized α-cyclodextrin derivatives for further confirming DIBAL-H-promoted bis-de-O-methylation mechanism », Tetrahedron, vol. 69, nᵒ 20, p. 4053-4060, 2013.
    Résumé : Abstract In our previous studies, a mechanism for DIBAL-H promoted regioselective bis-de-O-methylation of per-O-methylated cyclodextrin (CD) was proposed based on per-O-methylated β-CDs. As a further step to this work, four per-O-methylated α-CD derivatives (6, 7, 11, and 18) with mono functional group at the secondary rim have been designed and synthesized. Using DIBAL-H as a chemical ‘scalpel’, we found that (1) only the O-methyl at C-2A of 6 could be easily removed and (2) the O-methyl at C 3 B could be firstly regioselectively removed slowly, followed by a rapid removal of the second O-methyl at C 2 A to provide 3. Combined with our previous studies, we think that not only O-3B-methyl but also O-2A and O-3B are necessary for the formation of ‘tweezers’ during DIBAL-H promoted bis-de-O-methylation reaction of per-O-methylated CD.
    Mots-clés : DIBAL-H, GOBS, Mechanism, POLE 3, Synthesis, α-Cyclodextrin.


  • M. z de Person, A. Coffre, R. Skanji, M. Ben Messaouda, M. Abderraba, Y. Zhang, et F. Moussa, « Mechanism and number of adducts of photo-addition of glycine methyl-ester to [60] fullerene », Tetrahedron, vol. 69, nᵒ 33, p. 6826-6831, 2013.
    Résumé : Abstract Recently, it has been shown that visible light irradiation of a mixture of C60 and glycine methyl-ester in the presence of oxygen is a direct route to sequentially synthesize higher FP poly-adducts. However, the involved mechanism and the maximum number of pyrrolidine adducts per C60 molecule remained to be ascertained. Using high resolution mass spectrometry and HPLC–MS, we show here that the most probable mechanism involves a first step of azomethine ylide (AMY) formation followed by its [2+3] cyclo-addition to C60, and that the hexakis-adduct is the highest FP poly-adduct (FPPA) obtained under these conditions. Some FPPA and AMY dimers are also identified in the final mixture.
    Mots-clés : Azomethine ylide, Dimers, Fullerenes, GOBS, HPLC–MS, Photo-addition, POLE 3, Pyrrolidines.


  • E. Zaborova, M. Guitet, G. Prencipe, Y. Blériot, M. Ménand, et M. Sollogoub, « An “Against the Rules” Double Bank Shot with Diisobutylaluminum Hydride To Allow Triple Functionalization of α-Cyclodextrin », Angewandte Chemie International Edition, vol. 52, nᵒ 2, p. 639–644, 2013.
    Mots-clés : concave cycles, Cyclodextrin, GOBS, heterofunctionalization, mechanistic studies, POLE 3, selectivity.


  • X. Zhang, Y. Ito, J. Liang, Q. Su, Y. Zhang, J. Liu, et W. Sun, « Preparative isolation and purification of five steroid saponins from Dioscorea zingiberensis C.H.Wright by counter-current chromatography coupled with evaporative light scattering detector », Journal of Pharmaceutical and Biomedical Analysis, vol. 84, p. 117-123, oct. 2013.
    Résumé : A counter-current chromatography (CCC) method was successfully applied to separate and purify steroid saponins from the traditional Chinese medicine Dioscorea zingiberensis C.H.Wright for the first time. Ethyl acetate–n-butanol–methanol–water (4:1:2:4, v/v) was used as the two-phase solvent system, and evaporative light scattering detector (ELSD) was used as the detector in this method. The method separated in a single run the following five steroid saponins: 26-O-β-d-glucopyranosyl-(25R)-furost-5-en-3β, 22ζ, 26-triol-3-O-[β-d-glucopyranosyl-(1 → 3)-β-d-glucopyranol-(1 → 4)-α-l-rhamnopyranosyl-(1 → 2)]-β-d-glucopyranoside (Compound A); 26-O-β-d-glucopyranosyl-(25R)-furost-5-en-3β, 22ζ, 26-triol-3-O-[β-d-glucopyranosyl(1 → 3)-α-l-rhamnopyranosyl(1 → 2)]-β-d-glucopyranoside (Compound B); 26-O-β-d-glucopyranosyl-(25R)-furost-5-en-3β, 22ζ, 26-triol-3-O-[α-l-rhamnopyranosyl(1 → 4)]-β-d-glucopyranoside (Compound C); 26-O-β-d-glucopyranosyl-(25R)-furost-5, 20(22)-diene-3β, 26-diol-3-O-{α-l-rhamnopyranosyl-(1 → 4)-[β-d-glucopyranosyl-(1 → 3)-β-d-glucopyranosyl-(1 → 2)]}-β-d-glucopyranoside (Compound D); and 26-O-β-d-glucopyranosyl-(25R)-furost-5, 20(22)-diene-3β, 26-diol-3-O-[β-d-glucopyranosyl-(1 → 4)-α-l-rhamnopyranosyl(1 → 2)]-β-d-glucopyranoside (Compound E). Their structural identification of the five steroid saponins was performed by means of ESI-MS, and 13C NMR.
    Mots-clés : counter-current chromatography, Dioscorea zingiberensis C.H. Wright, Evaporative light scattering detector, GOBS, POLE 3, Steroid saponins, traditional chinese medicine.


  • W. Zhao, C. Sun, J. He, L. Chen, Y. Zhang, et W. Sun, « The possible mechanisms of Picrasma quassiodes (D. Don) Benn. in the treatment of colitis induced by 2,4,6-trinitrobenzene sulfonic acid in mice », Journal of Ethnopharmacology, vol. 145, nᵒ 2, p. 424-430, 2013.


  • W. Zhao, J. Yu, Q. Su, J. Liang, L. Zhao, Y. Zhang, et W. Sun, « Antihypertensive effects of extract from Picrasma quassiodes (D. Don) Benn. in spontaneously hypertensive rats », Journal of Ethnopharmacology, vol. 145, nᵒ 1, p. 187-192, 2013.

2012



  • G. a Izzet, M. Ménand, B. Matt, S. Renaudineau, L. - M. Chamoreau, M. Sollogoub, et A. Proust, « Cyclodextrin-Induced Auto-Healing of Hybrid Polyoxometalates », Angewandte Chemie International Edition, vol. 51, nᵒ 2, p. 487–490, 2012.
    Mots-clés : auto-healing, cyclodextrins, E-POM, GOBS, Host–guest systems, POLE 2, POLE 3, Polyoxometalates, POM.


  • L. Amorim, F. Marcelo, J. Désiré, M. Sollogoub, J. Jiménez-Barbero, et Y. Blériot, « Synthesis and conformational analysis of bicyclic mimics of α- and β-d-glucopyranosides adopting the biologically relevant 2,5B conformation », Carbohydrate Research, vol. 361, p. 219-224, nov. 2012.
    Résumé : The synthesis of three conformationally locked d-glucopyranoside analogs displaying the hydroxyl pattern of the parent sugar is described. A two carbon bridge connecting the C-2 and C-5 atoms of the pyranose ring allows a torsion of the sugar ring toward a 2,5B conformation as confirmed by conformational analysis. This conformation is strongly believed to be adopted by the oxacarbenium ion-like transition state of several inverting glucosidases.
    Mots-clés : Bicycle, Boat conformation, Glucopyranose, Glycosidase, GOBS, POLE 3.


  • J. Deschamp, M. Mondon, S. Nakagawa, A. Kato, D. S. Alonzi, T. D. Butters, Y. Zhang, M. Sollogoub, et Y. Blériot, « Towards a stable noeuromycin analog with a d-manno configuration: Synthesis and glycosidase inhibition of d-manno-like tri- and tetrahydroxylated azepanes », Bioorganic & Medicinal Chemistry, vol. 20, nᵒ 2, p. 641-649, janv. 2012.
    Résumé : Noeuromycin is a highly potent albeit unstable glycosidase inhibitor due to its hemiaminal function. While stable d-gluco-like analogs have been reported, no data are available for d-manno-like structures. A series of tri- and tetrahydroxylated seven-membered iminosugars displaying either a d-manno-or a l-gulo-like configuration, were synthesized from methyl α-d-mannopyranoside using a reductive amination-mediated ring expansion as the key step. Screening towards a range of commercial glycosidases demonstrated their potency as competitive glycosidase inhibitors while cellular assay showed selective albeit weak glycoprotein processing mannosidase inactivation.
    Mots-clés : Azepane, Glycosidase, GOBS, Iminosugar, Inhibition, POLE 3, Sugar mimic.

  • V. Dubee, M. Arthur, H. Fief, S. Triboulet, J. - L. Mainardi, L. Gutmann, M. Sollogoub, L. B. Rice, M. Etheve-Quelquejeu, et J. - E. Hugonnet, « Kinetic Analysis of Enterococcus faecium L,D-Transpeptidase Inactivation by Carbapenems », Antimicrobial Agents and Chemotherapy, vol. 56, nᵒ 6, p. 3409-3412, juin 2012.
    Résumé : Bypass of classical penicillin-binding proteins by the L,D-transpeptidase of Enterococcus faecium (Ldt(fm)) leads to high-level ampicillin resistance in E. faecium mutants, whereas carbapenems remain the lone highly active beta-lactams. Kinetics of Ldt(fm) inactivation was determined for four commercial carbapenems and a derivative obtained by introducing a minimal ethyl group at position 2. We show that the bulky side chains of commercial carbapenems have both positive and negative effects in preventing hydrolysis of the acyl enzyme and impairing drug binding.
    Mots-clés : antibiotics, biosynthesis, clavulanate, GOBS, meropenem, mycobacterium-tuberculosis, peptidoglycan cross-linking, POLE 3, resistance, transpeptidase.

  • N. Dupre, C. Brazel, L. Fensterbank, M. Malacria, S. Thorimbert, B. Hasenknopf, et E. Lacôte, « Self-Buffering Hybrid Gold-Polyoxometalate Catalysts for the Catalytic Cyclization of Acid-Sensitive Substrates », Chemistry-a European Journal, vol. 18, nᵒ 41, p. 12962-12965, 2012.
    Mots-clés : allenes, asymmetric enamine catalysts, carbene nhc complexes, CHEMBIO, COS, Cycloisomerization, epoxidation, GOBS, Gold, Heterocycles, heteropoly compounds, highly efficient, Hydroamination, intercluster compound, MACO, organic-inorganic hybrid composites, oxidation, POLE 1, POLE 3, Polyoxometalates, polyoxotungstates, protonation, SUPRA.


  • L. Eloy, A. - S. Jarrousse, M. - L. Teyssot, A. Gautier, L. Morel, C. Jolivalt, T. Cresteil, et S. Roland, « Anticancer Activity of Silver–N-Heterocyclic Carbene Complexes: Caspase-Independent Induction of Apoptosis via Mitochondrial Apoptosis-Inducing Factor (AIF) », ChemMedChem, vol. 7, nᵒ 5, p. 805–814, 2012.
    Résumé : Fourteen silver(I) complexes bearing N-heterocyclic carbene (NHC) ligands were prepared and evaluated for anticancer activity. Some of these were found to exhibit potent antiproliferative activity toward several types of human cancer cell lines, including drug-resistant cell lines, with IC50 values in the nanomolar range. An initial investigation into the mechanism of cell death induced by this family of silver(I) complexes was carried out. Cell death was shown to result from the activation of apoptosis without involvement of primary necrosis. In HL60 cells, silver–NHCs induce depolarization of the mitochondrial membrane potential (ΔΨm) and likely allow the release of mitochondrial proteins to elicit early apoptosis. This effect is not related to the overproduction of reactive oxygen species (ROS). In addition, apoptosis is not associated with the activation of caspase-3, but is triggered by the translocation of apoptosis-inducing factor (AIF) and caspase-12 from mitochondria and the endoplasmic reticulum, respectively, into the nucleus to promote DNA fragmentation and ultimately cell death. No modification in cell-cycle distribution was observed, indicating that silver–NHCs are not genotoxic. Finally, the use of a fluorescent complex showed that silver–NHCs target mitochondria. Altogether, these results demonstrate that silver–NHCs induce cancer cell death independent of the caspase cascade via the mitochondrial AIF pathway.
    Mots-clés : apoptosis-inducing factor, cancer, Carbene ligands, CHEMBIO, GOBS, Heterocycles, mode of action, POLE 3, silver.


  • Z. Guan, L. - H. Zhang, P. Sinaÿ, et Y. Zhang, « Study on Metal-Induced Reactions of α-Diazocarbonyl Glucosides », Journal of Organic Chemistry, vol. 77, nᵒ 20, p. 8888-8895, oct. 2012.
    Résumé : Conversions of diazocarbonyl carbohydrate compounds catalyzed by a series of rhodium and copper catalysts in conventional heating or microwave conditions were investigated. C?H insertion product was obtained in the presence of Rh2(OAc)4. Intermolecular reaction

    s rather than intramolecular reactions occurred in the presence of copper catalysts.
    Mots-clés : GOBS, POLE 3.


  • M. Guitet, S. A. de Beaumais, Y. Blériot, B. Vauzeilles, Y. Zhang, M. Ménand, et M. Sollogoub, « Cyclodextrins selectively modified on both rims using an O-3-debenzylative post-functionalisation, a consequence of the Sorrento meeting », Carbohydrate Research, vol. 356, p. 278-281, 2012.
    Résumé : A de-O-benzylation reaction induced by I2–Et3SiH and developed by Iadonisi et al. on mono- and disaccharides was applied to per- or polybenzylated α-cyclodextrins to furnish compounds deprotected at position 3 of all sugar units. This methodology allows the straightforward post-functionalisation of the secondary rim of cyclodextrins already functionalised on their primary rim.
    Mots-clés : Chemoselective, Cyclodextrin, Deprotection, GOBS, POLE 3, Post-functionalisation, Regioselective.


  • H. Li, Y. Zhang, S. Favre, P. Vogel, M. Sollogoub, et Y. Blériot, « Synthesis of branched seven-membered 1-N-iminosugars and their evaluation as glycosidase inhibitors », Carbohydrate Research, vol. 356, p. 110-114, 2012.
    Résumé : Four branched tetra- and pentahydroxylated azepanes have been synthesized from a common azepane precursor through dihydroxylation followed by deoxygenation. They have been assayed as glycosidase inhibitors on a panel of 22 glycosidases and one methylated azepane displayed selective, competitive, and moderate inhibition toward bovine kidney α-l-fucosidase.
    Mots-clés : Azepane, Glycosidase, GOBS, Iminosugar, Inhibitor, POLE 3.

  • J. Liang, J. He, S. Zhu, W. Zhao, Y. Zhao, Y. Zhang, et W. Sun, « An Expeditious Method Combining Multi-Components Determination And Fingerprinting Based On Ultra Performance Liquid Chromatography-Photo Diode Array-Tandem Mass Spectrometry And Chemometrics: Application For Authentication And Quality Evaluation Of Cornus Officinalis Sieb. Et Zucc », Analytical Letters, vol. 45, nᵒ 15, p. 2109-2124, 2012.
    Résumé : Selective and efficient analytical methods for authentication and quality evaluation of herbal medicines are significant and necessary. An expeditious method combining multi-components determination and fingerprinting based on ultra-performance liquid chromatography-photo diode array-tandem mass spectrometry (UPLC-PDA -MS/MS) and chemometrics for authentication and quality evaluation of Cornus Officinalis Sieb. et Zucc was developed. Tandem mass spectrometer operating in multiple reaction monitoring (MRM) was used for determination of three characteristic constituents (morroniside, sweroside, and loganin) in C. Officinalis. Meanwhile, UPLC fingerprint of C. Officinalis was established and the data set was submitted for classification to a suite of chemometrics method. Combing main biologically active components content level and chemometrics analysis, the effects of cultivation area, harvesting, and storage time on the quality of C. Officinalis were investigated. The study reveals that multi-components determination coupled with fingerprinting could be applied for authentication and quality evaluation of C. Officinalis which is accurate, efficient, and reliable.
    Mots-clés : Chemometrics, Cornus Officinalis Sieb. et Zucc, Fingerprint, fructus, GOBS, hplc, inflammation, loganin, mice, morroniside, Multi-components determination, POLE 3, Quality evaluation, uplc-ms/ms, uplc-pda-ms/ms.


  • J. Pérez-Castells, M. Fontanella, A. Ardá, F. J. Canãda, M. Sollogoub, Y. Blériot, et J. Jiménez-Barbero, « Conformational analysis of seven-membered 1-N-iminosugars by NMR and molecular modelling », New Journal of Chemistry, vol. 36, nᵒ 4, p. 1008-1013, avr. 2012.
    Résumé : The conformational analysis of a series of tri- and tetrahydroxyazepanes 1–6 designed as noeuromycin mimics has been carried out using 1H NMR spectroscopy assisted by molecular mechanics, molecular dynamics and Monte Carlo calculations. A marked flexibility for these compounds has been found. Superimposition
    Mots-clés : GOBS, POLE 3.


  • H. Qu, Y. Zhang, X. Chai, et W. Sun, « Isoforsythiaside, an antioxidant and antibacterial phenylethanoid glycoside isolated from Forsythia suspensa », Bioorganic Chemistry, vol. 40, p. 87-91, 2012.
    Résumé : The isolation, structural elucidation, antioxidant effect and antibacterial activity of isoforsythiaside, a novel phenylethanoid glycoside isolated from Forsythia suspensa, were described. The antioxidant activity was estimated using the 1-diphenyl-2-picrylhydrazyl scavenging activity method and the in vitro antimicrobial activity was evaluated by the microtitre plate method. The results showed that this compound had strong activities. Owing to these properties, the study can be further extended to exploit for the possible application of isoforsythiaside as the alternative antioxidants and antibacterial agents from natural origin.
    Mots-clés : Antibacterial, Antioxidant, Forsythia suspensa, Forsythiaside, GOBS, Isoforsythiaside, POLE 3, Structural elucidation.

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