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2023



  • M. Barbazanges, Y. Gimbert, et L. Fensterbank, « Gold-Catalyzed Addition of Propargyl Acetates to Olefins via O-Acyl Migration/Cyclopropanation Sequence: Insight into the Diastereoselective Formation of the Alkene », The Journal of Organic Chemistry, vol. 88, nᵒ 5, p. 3297-3302, mars 2023.
    Résumé : This article discloses a study on the well-known addition of propargyl acetates to olefins via an O-acyl migration/cyclopropanation sequence. Herein, we show that the stereochemical outcome of the olefin is strongly dependent on the gold catalyst and reaction parameters (concentration, temperature, and alkene partner equivalents); the E- and Z-isomers can be selectively formed by the judicious choice of reaction conditions.
    Mots-clés : CSOB, MACO, POLE 1, POLE 3.
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  • A. Beghennou, G. Gontard, H. Dossmann, K. Passador, S. Thorimbert, V. Corcé, et C. Botuha, « 1,6-Naphthyridin-7(6H)-ones: synthesis and optical properties », Organic & Biomolecular Chemistry, vol. 21, p. 2976-2982, mars 2023.
    Résumé : Efficient synthesis of original 1,6-naphthyridin-7(6H)-ones and their optical properties are described. Their powerful fluorescence properties including dual fluorescence, solvatochromism, acidochromism, large Stokes shifts and high quantum yields, suitable for biological applications or as luminescent devices in materials science, are evidenced.
    Mots-clés : CHEMBIO, CSOB, POLE 3.
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  • A. Mamontov, L. Chang, H. Dossmann, B. Bertrand, L. Dechoux, et S. Thorimbert, « Iron Catalyzed Dearomatization of Pyridines into Annelated Azepine Derivatives in a One-Step, Three-Component Reaction », Organic Letters, vol. 25, nᵒ 1, p. 256-260, 2023.
    Résumé : Commercially available Fe(TTP)Cl catalyzes three-component dearomative formal cycloaddition reactions between pyridines, diazo compounds, and coumalates. Diversely substituted annelated seven-membered N-heterocycles could be generated in less than 10 min in one step at room temperature. The reaction is compatible to gram scale. The extension to benzimidazoles in place of pyridines has been successfully demonstrated. The mechanism of this reaction has been carefully examined by computational studies that corroborate the observed regioselectivities.
    Mots-clés : CHEMBIO, CSOB, POLE 3.
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2022



  • P. Bayat, D. Gatineau, D. Lesage, A. Martinez, et R. B. Cole, « Benchmarking higher energy collision dissociation (HCD) by investigation of binding energies of gas‐phase host–guest complexes of hemicryptophane cages », Journal of Mass Spectrometry, vol. 57, nᵒ 9, p. e4879, 2022.


  • A. I. Carbajo‐Gordillo, J. López‐Fernández, J. M. Benito, J. L. Jiménez Blanco, M. L. Santana‐Armas, G. Marcelo, C. Di Giorgio, C. Przybylski, C. Ortiz Mellet, C. Tros de Ilarduya, F. Mendicuti, et J. M. García Fernández, « Enhanced Gene Delivery Triggered by Dual pH/Redox Responsive Host‐Guest Dimerization of Cyclooligosaccharide Star Polycations », Macromolecular Rapid Communications, vol. 43, nᵒ 11, p. 2200145, 2022.


  • A. Delvaux, E. Rathahao-Paris, et S. Alves, « Different ion mobility-mass spectrometry coupling techniques to promote metabolomics », Mass Spectrometry Reviews, vol. 41, nᵒ 5, p. 695-721, 2022.
    Résumé : Metabolomics has become increasingly popular in recent years for many applications ranging from clinical diagnosis, human health to biotechnological questioning. Despite technological advances, metabolomic studies are still currently limited by the difficulty of identifying all metabolites, a class of compounds with great chemical diversity. Although lengthy chromatographic analyses are often used to obtain comprehensive data, many isobar and isomer metabolites still remain unresolved, which is a critical point for the compound identification. Currently, ion mobility spectrometry is being explored in metabolomics as a way to improve metabolome coverage, analysis throughput and isomer separation. In this review, all the steps of a typical workflow for untargeted metabolomics are discussed considering the use of an ion mobility instrument. An overview of metabolomics is first presented followed by a brief description of ion mobility instrumentation. The ion mobility potential for complex mixture analysis is discussed regarding its coupling with a mass spectrometer alone, providing gas-phase separation before mass analysis as well as its combination with different separation platforms (conventional hyphenation but also multidimensional ion mobility couplings), offering multidimensional separation. Various instrumental and analytical conditions for improving the ion mobility separation are also described. Finally, data mining, including software packages and visualization approaches, as well as the construction of ion mobility databases for the metabolite identification are examined.
    Mots-clés : CSOB, hyphenated method, Ion mobility-mass spectrometry, metabolomics, multidimensional data, POLE 3.
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  • L. J. P. Dufour, A. M. Herrmann, J. Leloup, C. Przybylski, L. Foti, L. Abbadie, et N. Nunan, « Potential energetic return on investment positively correlated with overall soil microbial activity », Soil Biology and Biochemistry, vol. 173, p. 108800, 2022.


  • M. S. M. Holmsen, C. Blons, A. Amgoune, M. Regnacq, D. Lesage, E. D. Sosa Carrizo, P. Lavedan, Y. Gimbert, K. Miqueu, et D. Bourissou, « Mechanism of Alkyne Hydroarylation Catalyzed by (P,C)-Cyclometalated Au(III) Complexes », Journal of the American Chemical Society, vol. 144, nᵒ 49, p. 22722-22733, déc. 2022.


  • A. Hueber, Y. Gimbert, G. Langevin, J. - M. Galano, A. Guy, T. Durand, N. Cenac, J. Bertrand-Michel, et J. - C. Tabet, « Identification of bacterial lipo-amino acids: origin of regenerated fatty acid carboxylate from dissociation of lipo-glutamate anion », Amino Acids, vol. 54, nᵒ 2, p. 241-250, 2022.
    Résumé : Abstract The identification of bacterial metabolites produced by the microbiota is a key point to understand its role in human health. Among them, lipo-amino acids (LpAA), which are able to cross the epithelial barrier and to act on the host, are poorly identified. Structural elucidation of few of them was performed by high-resolution tandem mass spectrometry based on electrospray combined with selective ion dissociations reach by collision-induced dissociation (CID). The negative ions were used for their advantages of yielding only few fragment ions sufficient to specify each part of LpAA with sensitivity. To find specific processes that help structural assignment, the negative ion dissociations have been scrutinized for an LpAA: the N -palmitoyl acyl group linked to glutamic acid (C16Glu). The singular behavior of [C16Glu-H]¯ towards CID showed tenth product ions, eight were described by expected fragment ions. In contrast, instead of the expected product ions due to CONH-CH bond cleavage, an abundant complementary dehydrated glutamic acid and fatty acid anion pair were observed. Specific to glutamic moiety, they were formed by a stepwise dissociation via molecular isomerization through ion–dipole formation prior to dissociation. This complex dissociated by partner splitting either directly or after inter-partner proton transfer. By this pathway, surprising regeneration of deprotonated fatty acid takes place. Such regeneration is comparable to that occurred from dissociation to peptides containing acid amino-acid. Modeling allow to confirm the proposed mechanisms explaining the unexpected behavior of this glutamate conjugate.
    Mots-clés : CSOB, POLE 3.
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  • A. Hueber, M. Green, J. Ujma, K. Richardson, Y. Gimbert, N. Cenac, J. Bertrand-Michel, et J. - C. Tabet, « Energy-Resolved Ion Mobility Spectrometry: Composite Breakdown Curves for Distinguishing Isomeric Product Ions », Journal of the American Society for Mass Spectrometry, vol. 34, nᵒ 1, p. 36-47, déc. 2022.


  • A. Hueber, C. Petitfils, P. Le Faouder, G. Langevin, A. Guy, J. - M. Galano, T. Durand, J. - F. Martin, J. - C. Tabet, N. Cenac, et J. Bertrand-Michel, « Discovery and quantification of lipoamino acids in bacteria », Analytica Chimica Acta, vol. 1193, p. 339316, 2022.


  • M. Ndour, J. - P. Bonnet, S. Cavalaglio, T. Lombard, M. Courty, L. Aymard, C. Przybylski, et V. Bonnet, « The formulation of a CMC binder/silicon composite anode for Li-ion batteries: from molecular effects of ball milling on polymer chains to consequences on electrochemical performances », Materials Advances, vol. 3, nᵒ 23, p. 8522-8533, 2022.
    Résumé : The semi-synthetic polysaccharide carboxymethylcellulose (CMC) is one of the most studied and effective polymer binders for silicon-based anodes in Li-ion batteries. , The semi-synthetic polysaccharide carboxymethylcellulose (CMC) is one of the most studied and effective polymer binders for silicon-based anodes in Li-ion batteries. The formulation of the corresponding composite negative electrode with an appropriate mixture of electroactive silicon, a CMC binder and a carbon additive is mandatory to ensure a good electrical conductivity. Blending is commonly realized by a highly energetic ball milling treatment of these three aforementioned components. This type of mixing reduces the size of the obtained particles and can also potentially agglomerate them. Morever, it allows the formation of a nanostructured mixture which is essential for both the silicon activation and to achieve good electrochemical performance. However, such strong treatment can also cause a significant degradation of the polymer chains, as we have recently demonstrated for polyacrylic acid (PAA). In the present work, the structural and chemical effects of this mechanical grinding on three commercial CMCs ranging from 90 to 700 kg mol −1 were investigated. All the polymers were characterized using SEC-MALLS, FTIR spectroscopy, MALDI-TOF mass spectrometry and TGA-MS thermal analysis. In all cases, a huge average molecular weight decrease was noticed, leading to the appearance of a bimodal distribution with low (52–72 kg mol −1 ) to very low molecular weight populations (1–1.8 kg mol −1 ). From these results, two formulations of a negative electrode were compared, one with ball milling of the three compounds and another one including only ball milling steps for silicon and carbon. After the correlation of the characteristics of this negative electrode composite with the electrochemical results, it was demonstrated that a high number of functions for supramolecular or covalent linkages are keypoints of the herein anode performance. Low molecular weight CMC derivatives (about 64 kg mol −1 ) obtained by ball milling treatment led to higher stability of the electrode.
    Mots-clés : CSOB, POLE 3.
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  • N. Paulhe, C. Canlet, A. Damont, L. Peyriga, S. Durand, C. Deborde, S. Alves, S. Bernillon, T. Berton, R. Bir, A. Bouville, E. Cahoreau, D. Centeno, R. Costantino, L. Debrauwer, A. Delabrière, C. Duperier, S. Emery, A. Flandin, U. Hohenester, D. Jacob, C. Joly, C. Jousse, M. Lagree, N. Lamari, M. Lefebvre, C. Lopez-Piffet, B. Lyan, M. Maucourt, C. Migne, M. - F. Olivier, E. Rathahao-Paris, P. Petriacq, J. Pinelli, L. Roch, P. Roger, S. Roques, J. - C. Tabet, M. Tremblay-Franco, M. Traïkia, A. Warnet, V. Zhendre, D. Rolin, F. Jourdan, E. Thévenot, A. Moing, E. Jamin, F. Fenaille, C. Junot, E. Pujos-Guillot, et F. Giacomoni, « PeakForest: a multi-platform digital infrastructure for interoperable metabolite spectral data and metadata management », Metabolomics, vol. 18, nᵒ 6, p. 40, 2022.
    Résumé : Abstract Introduction Accuracy of feature annotation and metabolite identification in biological samples is a key element in metabolomics research. However, the annotation process is often hampered by the lack of spectral reference data in experimental conditions, as well as logistical difficulties in the spectral data management and exchange of annotations between laboratories. Objectives To design an open-source infrastructure allowing hosting both nuclear magnetic resonance (NMR) and mass spectra (MS), with an ergonomic Web interface and Web services to support metabolite annotation and laboratory data management. Methods We developed the PeakForest infrastructure, an open-source Java tool with automatic programming interfaces that can be deployed locally to organize spectral data for metabolome annotation in laboratories. Standardized operating procedures and formats were included to ensure data quality and interoperability, in line with international recommendations and FAIR principles. Results PeakForest is able to capture and store experimental spectral MS and NMR metadata as well as collect and display signal annotations. This modular system provides a structured database with inbuilt tools to curate information, browse and reuse spectral information in data treatment. PeakForest offers data formalization and centralization at the laboratory level, facilitating shared spectral data across laboratories and integration into public databases. Conclusion PeakForest is a comprehensive resource which addresses a technical bottleneck, namely large-scale spectral data annotation and metabolite identification for metabolomics laboratories with multiple instruments. PeakForest databases can be used in conjunction with bespoke data analysis pipelines in the Galaxy environment, offering the opportunity to meet the evolving needs of metabolomics research. Developed and tested by the French metabolomics community, PeakForest is freely-available at https://github.com/peakforest .
    Mots-clés : CSOB, POLE 3.
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  • C. Przybylski et V. Bonnet, « Probing topology of supramolecular complexes between cyclodextrins and alkali metals by ion mobility-mass spectrometry », Carbohydrate Polymers, vol. 297, p. 120019, 2022.


  • E. Rathahao‐Paris, A. Delvaux, M. Li, B. Guillon, E. Venot, F. Fenaille, K. Adel‐Patient, et S. Alves, « Rapid structural characterization of human milk oligosaccharides and distinction of their isomers using trapped ion mobility spectrometry time‐of‐flight mass spectrometry », Journal of Mass Spectrometry, vol. 57, nᵒ 10, p. e4885, 2022.


  • F. Zhao, M. Abdellaoui, W. Hagui, M. Ballarin-Marion, J. Berthet, V. Corcé, S. Delbaere, H. Dossmann, A. Espagne, J. Forté, L. Jullien, T. Le Saux, V. Mouriès-Mansuy, C. Ollivier, et L. Fensterbank, « Reactant-induced photoactivation of in situ generated organogold intermediates leading to alkynylated indoles via Csp2-Csp cross-coupling », Nature Communications, vol. 13, nᵒ 1, p. 2295, avr. 2022.
    Résumé : Photosensitization of organogold intermediates is an emerging field in catalysis. In this context, an access to 2,3-disubstituted indoles from o-alkynyl aniline and iodoalkyne derivatives via a gold-catalyzed sequence under visible-light irradiation and in the absence of an exogenous photocatalyst was uncovered. A wide scope of the process is observed. Of note, 2-iodo-ynamides can be used as electrophiles in this cross-coupling reaction. The resulting N-alkynyl indoles lend themselves to post-functionalization affording valuable scaffolds, notably benzo[a]carbazoles. Mechanistic studies converge on the fact that a potassium sulfonyl amide generates emissive aggregates in the reaction medium. Static quenching of these aggregates by a vinylgold(I) intermediate yields to an excited state of the latter, which can react with an electrophile via oxidative addition and reductive elimination to forge the key C-C bond. This reactant-induced photoactivation of an organogold intermediate opens rich perspectives in the field of cross-coupling reactions.
    Mots-clés : CHEMBIO, CSOB, MACO, Photocatalysis, POLE 1, POLE 3, Reaction mechanisms.
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2021



  • A. I. Carbajo‐Gordillo, M. González‐Cuesta, J. L. Jiménez Blanco, J. M. Benito, M. L. Santana‐Armas, T. Carmona, C. Di Giorgio, C. Przybylski, C. Ortiz Mellet, C. Tros de Ilarduya, F. Mendicuti, et J. M. García Fernández, « Trifaceted Mickey Mouse Amphiphiles for Programmable Self‐Assembly, DNA Complexation and Organ‐Selective Gene Delivery », Chemistry – A European Journal, vol. 27, nᵒ 36, p. 9429-9438, juin 2021.


  • A. Damont, A. Legrand, C. Cao, F. Fenaille, et J. ‐C. Tabet, « Hydrogen/deuterium exchange mass spectrometry in the world of small molecules », Mass Spectrometry Reviews, p. e21765, déc. 2021.


  • E. Darii, Y. Gimbert, S. Alves, A. Damont, A. Perret, A. S. Woods, F. Fenaille, et J. - C. Tabet, « First Direct Evidence of Interpartner Hydride/Deuteride Exchanges for Stored Sodiated Arginine/Fructose-6-phosphate Complex Anions within Salt-Solvated Structures », Journal of the American Society for Mass Spectrometry, vol. 32, nᵒ 6, p. 1424-1440, juin 2021.


  • A. Delvaux, E. Rathahao-Paris, B. Guillon, S. Cholet, K. Adel-Patient, F. Fenaille, C. Junot, et S. Alves, « Trapped ion mobility spectrometry time-of-flight mass spectrometry for high throughput and high resolution characterization of human milk oligosaccharide isomers », Analytica Chimica Acta, vol. 1180, p. 338878, 2021.


  • D. Gatineau, H. Dossmann, H. Clavier, A. Memboeuf, L. Drahos, Y. Gimbert, et D. Lesage, « Ligand effects in gold-carbonyl complexes: evaluation of the bond dissociation energies using blackbody infrared radiative dissociation », International Journal of Mass Spectrometry, vol. 463, p. 116545, févr. 2021.


  • A. Gillet, S. Cher, M. Tassé, T. Blon, S. Alves, G. Izzet, B. Chaudret, A. Proust, P. Demont, F. Volatron, et S. Tricard, « Polarizability is a key parameter for molecular electronics », Nanoscale Horizons, vol. 6, nᵒ 3, p. 271-276, mars 2021.
    Résumé : Identifying descriptors that govern charge transport in molecular electronics is of prime importance for the elaboration of devices. The effects of molecule characteristics, such as size, bulkiness or charge, have been widely reported. Herein, we show that the molecule polarizability can be a crucial parameter to consider. To this end, platinum nanoparticle self-assemblies (PtNP SAs) are synthesized in solution, including a series of polyoxometalates (POMs). The charge of the POM unit can be modified according to the nature of the central heteroatom while keeping its size constant. POM hybrids that display remote terminal thiol functions strongly anchor the PtNP surface to form robust SAs. IV curves, recorded by conductive AFM, show a decrease in Coulomb blockade as the dielectric constant of the POMs increases. In this system, charge transport across molecular junctions can be interpreted as variations in polarizability, which is directly related to the dielectric constant.
    Mots-clés : CSOB, E-POM, POLE 2, POLE 3.
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  • S. Khodjoyan, E. Remadna, H. Dossmann, D. Lesage, G. Gontard, J. Forté, H. Hoffmeister, U. Basu, I. Ott, P. Spence, Z. Waller, M. Salmain, et B. Bertrand, « [(C^C)Au(N^N)]+ complexes as a new family of anticancer candidates: synthesis, characterization and exploration of the antiproliferative properties », Chemistry – A European Journal, vol. 27, nᵒ 63, p. 15773-15785, 2021.
    Résumé : A library of eleven cationic gold(III) complexes of the general formula [(C^C)Au(N^N)] + when C^C is either biphenyl or 4,4’-ditertbutyldiphenyl and N^N is a bipyridine, phenanthroline or dipyridylamine derivative have been synthesized and characterized. Contrasting effects on the viability of the triple negative breast cancer cells MDA-MB-231 was observed from a preliminary screening. The antiproliferative activity of the seven most active complexes were further assayed on a larger panel of human cancer cells as well as on non-cancerous cells for comparison. Two complexes stood out for being either highly active or highly selective. Eventually, reactivity studies with biologically meaningful amino acids, glutathione, higher order DNA structures and thioredoxin reductase (TrxR) revealed a markedly different behavior from that of the well-known coordinatively isomeric [(C^N^C)Au(NHC)] + structure. This makes the [(C^C)Au(N^N)] + complexes a new class of organogold compounds with an original mode of action.
    Mots-clés : Bioorganometallics, Biphenyl, Cancer, Chelate, CHEMBIO, CSOB, Gold, POLE 3.
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  • S. Maletić, I. Ivančev-Tumbas, A. Brossas, M. Antonijević, J. Čáslavský, B. Jovančićević, Z. Matović, R. Kongoli, MajlindaVasjari, M. Petrović, N. Andrejić, S. Popov, N. L. Vesović, J. - C. Tabet, A. Warnet, Darko Anđelković, G. Gajica, et T. Anđelković, « Overview of Erasmus+ NETCHEM project: ICT networking for overcoming technical and social barriers in instrumental analytical chemistry education », Environmental Science and Pollution Research, vol. 28, nᵒ 2, p. 2479-2483, 2021.


  • R. Ramos, J. - F. Gilles, R. Morichon, C. Przybylski, B. Caron, C. Botuha, A. Karaiskou, M. Salmain, et J. Sobczak-Thépot, « Cytotoxic BODIPY-Appended Half-Sandwich Iridium(III) Complex Forms Protein Adducts and Induces ER Stress », Journal of Medicinal Chemistry, vol. 64, nᵒ 22, p. 16675-16686, nov. 2021.
    Résumé : Half-sandwich complexes of iridium(III) are currently being developed as anticancer drug candidates. In this context, we introduce IrBDP for which the C^N chelating phenyloxazoline ligand carries a fluorescent and lipophilic BODIPY reporter group, designed for intracellular tracking and hydrophobic compartment tropism. High-resolution analysis of cells cultured with IrBDP showed that it quickly permeates the plasma membrane and accumulates in the mitochondria and endoplasmic reticulum (ER), generating ER stress, dispersal of the Golgi apparatus, cell proliferation arrest and apoptotic cell death. Moreover, IrBDP forms fluorescent adducts with a subset of amino acids, namely histidine and cysteine, via coordination of N or S donor atoms of their side chains. Consistently, in vivo formation of covalent adducts with specific proteins is demonstrated, providing a molecular basis for the observed cytotoxicity and cellular response. Collectively, these results provide a new entry to the development of half-sandwich iridium-based anticancer drugs.
    Mots-clés : CHEMBIO, CSOB, POLE 3.
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  • E. Rathahao-Paris, S. Alves, et A. Paris, « High-Throughput Metabolomics Using Flow Injection Analysis and Fourier Transform Ion Cyclotron Resonance Mass Spectrometry », in Metabolomics, vol. 159, New York, NY: Humana, 2021, p. 9-23.
    Résumé : The hyphenation of flow injection analysis (FIA) with Fourier transform ion cyclotron resonance mass spectrometry (FTICR-MS) is an efficient approach usable to perform high throughput and very high resolution metabolomic data acquisition. Instrumental and analytical conditions for performing FIA-MS are provided. The procedure to optimize dilution factor of biological samples as well as to evaluate quality of acquisition data are also described. In this protocol, urine is chosen as a matrix example to illustrate the application of procedures. Last, some indications on an adapted data processing are given.
    Mots-clés : CSOB, POLE 3.
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  • M. Raynal, Y. Li, C. Troufflard, C. Przybylski, G. Gontard, T. Maistriaux, J. Idé, R. Lazzaroni, L. Bouteiller, et P. Brocorens, « Experimental and computational diagnosis of the fluxional nature of a benzene-1,3,5-tricarboxamide-based hydrogen-bonded dimer », Physical Chemistry Chemical Physics, vol. 23, nᵒ 9, p. 5207-5221, 2021.
    Résumé : High-symmetry (left) and low-symmetry ( e.g. that on the right) conformations of benzene-1,3,5-tricarboxamide dimers derived from glycine alkyl esters are in rapid exchange in solution through amide/ester competition for the binding of the N–H donors. , Precise characterization of the hydrogen bond network present in discrete self-assemblies of benzene-1,3,5-tricarboxamide monomers derived from amino-esters (ester BTAs) is crucial for the construction of elaborated functional co-assemblies. For all ester BTA dimeric structures previously reported, ester carbonyls in the side chain acted as hydrogen bond acceptors, yielding well-defined dimers stabilized by six hydrogen bonds. The ester BTA monomer derived from glycine ( BTA Gly ) shows a markedly different self-assembly behaviour. We report herein a combined experimental and computational investigation aimed at determining the nature of the dimeric species formed by BTA Gly . Two distinct dimeric structures were characterized by single-crystal X-ray diffraction measurements. Likewise, a range of spectroscopic and scattering techniques as well as molecular modelling were employed to diagnose the nature of dynamic dimeric structures in toluene. Our results unambiguously establish that both ester and amide carbonyls are involved in the hydrogen bond network of the discrete dimeric species formed by BTA Gly . The participation of roughly 4.5 ester carbonyls and 1.5 amide carbonyls per dimer as determined by FT-IR spectroscopy implies that several conformations coexist in solution. Moreover, NMR analysis and modelling data reveal rapid interconversion between these different conformers leading to a symmetric structure on the NMR timescale. Rapid hydrogen bond shuffling between conformers having three (three), two (four), one (five) and zero (six) amide carbonyl groups (ester carbonyl groups, respectively) as hydrogen bond acceptors is proposed to explain the magnetic equivalence of the amide N–H on the NMR timescale. When compared to other ester BTA derivatives in which only ester carbonyls act as hydrogen bond acceptors, the fluxional behaviour of the hydrogen-bonded dimers of BTA Gly likely originates from a larger range of energetically favorable conformations accessible through rotation of the BTA side chains.
    Mots-clés : CSOB, POLE 3, POLE 4, POLYMERES.
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  • J. - C. Tabet, Y. Gimbert, A. Damont, D. Touboul, F. Fenaille, et A. S. Woods, « Combining Chemical Knowledge and Quantum Calculation for Interpreting Low-Energy Product Ion Spectra of Metabolite Adduct Ions: Sodiated Diterpene Diester Species as a Case Study », Journal of the American Society for Mass Spectrometry, vol. 32, nᵒ 10, p. 2499-2504, oct. 2021.


  • W. Wang, C. Przybylski, X. Cai, C. Lopin-Bon, R. Jiao, L. Shi, K. Sugahara, J. L. Neira, R. Daniel, et F. Li, « Investigation of action pattern of a novel chondroitin sulfate/dermatan sulfate 4- <i>O</i> -endosulfatase », Biochemical Journal, vol. 478, nᵒ 2, p. 281-298, janv. 2021.
    Résumé : Recently, a novel CS/DS 4-O-endosulfatase was identified from a marine bacterium and its catalytic mechanism was investigated further (Wang, W., et. al (2015) J. Biol. Chem.290, 7823–7832; Wang, S., et. al (2019) Front. Microbiol.10, 1309). In the study herein, we provide new insight about the structural characteristics of the substrate which determine the activity of this enzyme. The substrate specificities of the 4-O-endosulfatase were probed by using libraries of structure-defined CS/DS oligosaccharides issued from synthetic and enzymatic sources. We found that this 4-O-endosulfatase effectively remove the 4-O-sulfate of disaccharide sequences GlcUAβ1-3GalNAc(4S) or GlcUAβ1-3GalNAc(4S,6S) in all tested hexasaccharides. The sulfated GalNac residue is resistant to the enzyme when adjacent uronic residues are sulfated as shown by the lack of enzymatic desulfation of GlcUAβ1-3GalNAc(4S) connected to a disaccharide GlcUA(2S)β1-3GalNAc(6S) in an octasaccharide. The 3-O-sulfation of GlcUA was also shown to hinder the action of this enzyme. The 4-O-endosulfatase exhibited an oriented action from the reducing to the non-reducing whatever the saturation or not of the non-reducing end. Finally, the activity of the 4-O-endosulfatase decreases with the increase in substrate size. With the deeper understanding of this novel 4-O-endosulfatase, such chondroitin sulfate (CS)/dermatan sulfate (DS) sulfatase is a useful tool for exploring the structure–function relationship of CS/DS.
    Mots-clés : CSOB, POLE 3.
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  • N. V. Yerra, B. Dyaga, S. B. Dadinaboyina, S. Pandeti, J. R. Vaidya, J. - C. Tabet, et J. R. Thota, « 2-Cyano-3-(2-thienyl)acrylic Acid as a New MALDI Matrix for the Analysis of a Broad Spectrum of Analytes », Journal of the American Society for Mass Spectrometry, vol. 32, nᵒ 1, p. 387-393, janv. 2021.

2020

2019



  • C. M. Kronfel, C. V. Hernandez, J. P. Frick, L. S. Hernandez, A. Gutu, J. A. Karty, M. N. Boutaghou, D. M. Kehoe, R. B. Cole, et W. M. Schluchter, « CpeF is the bilin lyase that ligates the doubly linked phycoerythrobilin on β-phycoerythrin in the cyanobacterium <i>Fremyella diplosiphon</i> », Journal of Biological Chemistry, vol. 294, nᵒ 11, p. 3987–3999, janv. 2019.


  • D. Lesage, S. Mezzache, Y. Gimbert, H. Dossmann, et J. - C. Tabet, « Extended kinetic method and RRKM modeling to reinvestigate proline’s proton affinity and approach the meaning of effective temperature », European Journal of Mass Spectrometry, vol. 25, nᵒ 2, p. 219-228, janv. 2019.


  • C. Przybylski, H. Ramoul, V. Bonnet, M. Abad, et N. Jarroux, « Harnessing Polyisobutylene by Rotaxanation with γ-Cyclodextrin: Opportunities for Making Smart Molecular Necklaces », Macromolecular Chemistry and Physics, vol. 220, nᵒ 5, p. 1800502, mars 2019.
    Résumé : Abstract A new type of polyrotaxane based on the threading of ?-cyclodextrins (?-CDs) along a highly hydrophobic polymer, polyisobutylene (PIB), is successfully prepared and finely characterized. The used radical coupling associated with tuned reaction time and temperature leads to a fast and controlled necklace synthesis with low reagent consumption. Synthesis exhibits appealing conversion and threading rates with almost 100% and 62?73%, respectively. A combination of well-established SEC and NMR techniques, with a more forefront MALDI-TOF MS approach, provides details on the original PIB and the resulting polyrotaxanes (M w, M n, PDI, and average number of ?-CD threaded). Interestingly, tetramethylguanidinium-2-(4-hydroxyphenylazo)benzoate in DMF for MALDI analysis is revealed as a suitable matrix to overcome solubility troubles widely observed with PIB. Moreover, rotaxanation appears as an alternative to the grafting of polar groups to modify/handle hydrophobic polymers. Such an approach offers new opportunities to achieve the synthesis, with unambiguous evidence, of new supramolecular necklaces based on highly hydrophobic polymers.
    Mots-clés : CSOB, cyclodextrins, mass spectrometry, POLE 3, polyisobutylene, polyrotaxane, radical coupling.
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  • I. Seffouh, C. Przybylski, A. Seffouh, R. El Masri, R. R. Vivès, F. Gonnet, et R. Daniel, « Mass spectrometry analysis of the human endosulfatase Hsulf-2 », Biochemistry and Biophysics Reports, vol. 18, p. 100617, juill. 2019.
    Résumé : The human 6-O-endosulfatases HSulf-1 and -2 catalyze the region-selective hydrolysis of the 6-O-sulfate group of the glucosamine residues within sulfated domains of heparan sulfate, thereby ensuring a unique and original post-biosynthetic modification of the cell surface proteoglycans. While numerous studies point out the role of HSulf-2 in crucial physiological processes as well as in pathological conditions particularly in cancer, its structural organization in two chains and its functional properties remain poorly understood. In this study, we report the first characterization by mass spectrometry (MS) of HSulf-2. An average molecular weight of 133,115 Da was determined for the whole enzyme by MALDI-TOF MS, i.e. higher than the naked amino acid backbone (98,170 Da), highlighting a significant contribution of post-translational modifications. The HSulf-2 protein sequence was determined by Nano-LC-MS/MS, leading to 63% coverage and indicating at least four N-glycosylation sites at Asn 108, 147, 174 and 217. These results provide a platform for further structural investigations of the HSulf enzymes, aiming at deciphering the role of each chain in the substrate binding and specificities and in the catalytic activities.
    Mots-clés : 6--Endosulfatase, CSOB, Formylglycine, Heparan sulfate, HSulf-2, Mass spectrometry, POLE 3, Sulfatase.
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2018

2017

2015



  • D. Lesage, G. Barozzino-Consiglio, R. Duwald, C. Fressigné, A. Harrison-Marchand, K. F. Faull, J. Maddaluno, et Y. Gimbert, « A Lithium Amide Protected Against Protonation in the Gas Phase: Unexpected Effect of LiCl », The Journal of Organic Chemistry, vol. 80, nᵒ 12, p. 6441-6446, 2015.
    Résumé : In cold THF and in the presence of LiCl, a lithium pyrrolidinylamide forms a 1:1 mixed aggregate, which is observed directly by ESI-MS. Gas-phase protonation of this species leads to selective transfer of H+ to the chlorine, suggesting that LiCl shields the amide nitrogen and prevents its direct protonation.
    Mots-clés : CSOB, POLE 3.
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