Principaux résultats

Références 2016-2020

1- Alabdulmagid, A.; Bliard, C.; Boudesocque, S.; Bouquillon, S.; Coqueret, X.; Dupont, L.; Edwards, F.; Gérard, S.; Guillermain, C.; Guillon, E.; Haudrechy, A.; Hoffmann, N.; Hubert, J.; Kowandy, C.; Lavaud, C.; Mohamadou, A.; Muzard, M.; Nuzillard, J.-M.; Plantier-Royon, R.; Rémond, C.; Sapi, J.; Sayen, S.; Tataru, G.; Renault, J.-H. Chimie du végétal et produits innovants à forte valeur ajoutée. L’Act. Chim. 2018, 427-428, 25-33. Réf. HAL: hal-02266305

2- De Gaetano, Y.; Hubert, J.; Mohamadou, A.; Boudesocque, S.; Plantier-Royon, R.; Renault, J.-H.; Dupont, L. Removal of pesticides from wastewater by ion pair centrifugal partition extraction using betaine-derived ionic liquids as extractants. Chem. Eng. J. 2016, 285, 596-604. doi: Réf. HAL: hal-01889373

3- Flourat, A. L.; Peru, A. A. M.; Haudrechy, A.; Renault, J.-H.; Allais, F. First total synthesis of (beta-5)-(beta-O-4) dihydroxytrimer and dihydrotrimer of coniferyl alcohol (G): advanced lignin model compounds. Front. Chem. 2019, 7, 842-850. doi: Réf. HAL: hal-02400612

4- Gatard, S.; Plantier-Royon, R.; Rémond, C.; Muzard, M.; Kowandy, C.; Bouquillon S. Preparation of new beta-D-xyloside- and beta-D-xylobioside-based ionic liquids through chemical and/or enzymatic reactions. Carbohydr. Res. 2017, 451, 72-80. doi: Réf. HAL: hal-01886797

5- Chatron-Colliet, A.; Brusa, C.; Bertin-Jung, I.; Gulberti, S.; Ramalanjaona, N.; Fournel-Gigleux, S.; Brézillon, S.; Muzard, M.; Plantier-Royon, R.; Rémond, C.; Wegrowski, Y. “Click”-glycosides as initiators of the biosynthesis of glycosaminoglycans: comparison of mono-xylosides with xylobiosides. Chem. Biol. Drug. Des. 2017, 89, 319-326. doi: Réf. HAL: hal-01601622

6- Brusa, C.; Belloy, N.; Gérard, D.; Muzard, M.; Dauchez, M.; Plantier-Royon, R.; Rémond, C. Exploring the aglycone subsite of a GH11 xylanase for the synthesis of xylosides by transglycosylation reactions. J. Biotechnol. 2018, 272-273, 56-63. doi: Réf. HAL: hal-02056771

7- Méline, T.; Muzard, M.; Deleu, M.; Rakotoarivonina, H.; Plantier-Royon, R.; Rémond, C. D-Xylose and L-arabinose laurate esters : enzymatic synthesis, characterization and physico-chemical properties. Enzyme Microb. Technol. 2018, 112, 14-21. doi: Réf. HAL: hal-01763242

8- Résultats non publiés soumis à Carbohydr. Res.

9- Mohammed, F.; Guillaume, D.; Abdulwali, N.; Bchitou, R.; El Hajjaji S.; Bouhaouss. Element content is a highly reliable marker for niche vegetable oils. Nat. Prod. Commun. 2018, 13, 5, 609-611.

10- Ennoukh, F. E.; Bchitou, R.; Mohammed, F.; Guillaume, D.; Harhar, H.; Bouhaouss, A. Study of the effects of extraction methods on argan oil quality through its metal content. Ind. Crops Prod. 2017, 109, 182-184.

11- Mohammed, F.; Abdulwali, N.; Guillaume, D.; Tenyang, N.; Ponka, R.; Al-Gadabi, K.; Bchitou, R.; Abdullah, A. H.; Naji, K. M. Chemical composition and mineralogical residence of sesame oil from plants grown in different Yemeni environments. Microchem. J. 2018, 140, 269-277.

12- Hajib, A.; Harhar, H.; Gharby, S.; Nounah, I.; Matthäus, B.; Guillaume, D.; Charrouf, Z. Is geographic origin a good marker for cumin seed oil (Cuminum cyminum L.)? Riv. Ital. Sostanze Gr. 2018, 95, 155-159.

13- Nounah, I.; Hajib, A.; Harhar, H.; El Madani, N.; Gharby, S.; Guillaume, D.; Charrouf, Z. Chemical composition and antioxidant activity of Lawsonia inermis seed extracts from Morocco. Nat. Prod. Commun. 2017, 12, 4, 487-488.

14- Mohammed, F.; Guillaume, D.; Abdulwali, N.; Zabara, B.; Bchitou, R. Tin content is a possible marker to discriminate argan oil against olive, sesame, mustard, corn, peanut, and sunflower oils. Eur. J. Lipid Sci. Tech. 2019, 121, 1800180.

15- Mohammed, F.; Abdulwali, N.; Guillaume, D.; Bchitou, R. Element content of Yemeni honeys as a long-time marker to ascertain honey botanical origin and quality. LWT-Food Sci. Technol. 2018, 88, 43-46.

16- Mohammed, F.; Guillaume, D.; Dowman, S.; Abdulwali, N. An easy way to discriminate Yemeni against Ethiopian coffee. Microchem. J. 2019, 145, 173-179.

17- Noté, O. P.; Azouaou, S. A.; Simo, L.; Antheaume, C.; Guillaume, D.; Pegnyemb, D. E.; Muller, C. D.; Lobstein, A. Phenotype-specific apoptosis induced by three new triterpenoid saponins from Albizia glaberrima (Schumach & Thonn.) Benth. Fitoterapia 2016, 109, 80-86. doi: Réf. HAL: hal-02106918

18- Noté, O. P.; Messi, L. M.; Mbing, J. N.; Azouaou, S. A.; Sarr, M.; Guillaume, D.; Muller, C. D.; Pegnyemb, D. E.; Lobstein, A. Pro-apoptotic activity of acylated triterpenoid saponins from the stem bark of Albizia chevalieri harms. Phytochem. Lett. 2017, 22, 95-101. doi: Réf. HAL: hal-02106899

19- Noté, O. P.; Simo, L.; Mbing, J. N.; Guillaume, D.; Azouaou, S. A.; Muller, C. D.; Pegnyemb, D. E.; Lobstein, A. Two new triterpenoid saponins from the roots of Albizia zygia (DC.) J.F. Macbr. Phytochem. Lett. 2016, 18, 128-135. doi: Réf. HAL: hal-02106916

20- Noté, O. P.; Simo, L. M.; Mbing, J. N.; Guillaume, D.; Muller, C. D.; Pegnyemb, D. E.; Lobstein, A. Structural determination of two new acacic acid-type saponins from the stem barks of Albizia zygia (DC.) J.F. Macbr. Nat. Prod. Res. 2018, 33, 2, 180-188.

21- Simo, L. M.; Noté, O. P.; Mbing, J. N.; Azouaou, S. A.; Guillaume, D.; Muller, C. D.; Pegnyemb, D. E.; Lobstein, A. New cytotoxic triterpenoid saponins from the roots of Albizia gummifera (J.F.Gmel.) C.A.Sm. Chem. Biodivers. 2017, 14, e1700260. doi: Réf. HAL: hal-02106897

22- Noté, O. P.; Le Doux Kamto, E.; Toukea, D. D.; Azouaou, S. A.; Mbing, J. N.; Muller, C. D.; Guillaume, D.; Pegnyemb, D. E. Pro-apoptotic activity of new triterpenoid saponins from the roots of Albizia adianthifolia (Schumach.) W.Wight. Fitoterapia 2018, 129, 34-41. doi: Réf. HAL: hal-02106792

23- Goekjian, P.; Haudrechy, A.; Menhour, B.; Coiffier, C. C-Furanosides. Topics in Stereochemistry. 2018, Academic Press.

24- Belhomme, M.-C.; Castex, S.; Haudrechy, A. Dehydration of hexoses, in "Handbook of Molecular Gastronomy: scientific foundations and culinary applications". 2018, CRC Press Eds.

25- Belhomme, M.-C.; Castex, S.; Haudrechy, A. « Sugar mapping », an easy-to-use visual tool to help the synthetic chemist identify carbohydrate stereochemical relationships. J. Chem. Educ. 2019, 96, 2643-2648. doi: Réf. HAL: hal-02504338

26- Résultats non publiés soumis à Chem. Eur. J. (Thèse M. Fortunato, "Préparation et applications de nouveaux xylosides comportant des aglycones fonctionnalisés pour la synthèse organique et la catalyse homogène", collaboration Dr. F. Jaroschik, ENSC Montpellier, soutenue à Reims le jeudi 12 décembre 2019).

27- Habilitation à Diriger des Recherches, Sylvain Gatard, soutenue à Reims le mercredi 27 mars 2019.

28- Moreaux, M.; Bonneau, G.; Peru, A.; Brunissen, F.; Janvier, M.; Haudrechy, A.; Allais, F. High-yielding diastereoselective syn-dihydroxylation of protected HBO: an access to D-(+)-ribono-1,4-lactone and 5-O-protected analogues. Eur. J. Org. Chem. 2019, 7, 1600-1604. doi: Réf. HAL: hal-02052678

29- Flourat, A. L.; Haudrechy, A.; Allais, F.; Renault J.-H. (S)-gamma-hydroxymethyl-alpha,beta-butenolide (aka HBO), a valuable chiral synthon : syntheses, reactivity and applications. Org. Process Res. Dev. 2019. doi: Réf. HAL: hal-02400639

30- Moriou, C.; Da Silva, A. D.; Vianelli Prado, M. J.; Denhez, C.; Plashkevych, O.; Chattopadhyaya, J.; Guillaume, D.; Clivio, P. C2’-F Stereoconfiguration as a puckering switch for base stacking at the dinucleotide level. J. Org. Chem. 2018, 83, 2473-2478. doi: Réf. HAL: hal-02380411

31- Coantic-Castex, S.; Martinez, A.; Harakat, D.; Guillaume, D.; Clivio, P. The remarkable UV light invulnerability of thymine GNA dinucleotides. Chem. Commun. 2019, 55, 12571-12574. doi: Réf. HAL: hal-02380447

32- Lameiras, P.; Patis, S.; Jakhlal, J.; Castex, S.; Clivio, P.; Nuzillard, J.-M. Small molecule mixture analysis by heteronuclear NMR under spin diffusion conditions in viscous DMSO-water solvent. Chem. Eur. J. 2017, 23, 4923-4928. doi: Réf. HAL: hal-01800195

33- Flos, M.; Lameiras, P.; Denhez, C.; Mirand, C.; Berber, H. Atropisomerism about aryl-C(sp3) bonds: conformational behavior of substituted phenylcyclohexanes in solution. J. Org. Chem. 2016, 81, 2372-2382.

34- Denhez, C.; Lameiras, P.; Flos, M.; Mirand, C.; Berber, H. Benzoyl groups as ortho-substituents in cannabidiol derivatives: controlling axial conformation about aryl-C(sp3) bonds. Eur. J. Org. Chem. 2019, 2, 360-368.

35- Denhez, C.; Lameiras, P.; Berber, H. Intramolecular OH/p versus CH/OH-bond-dependent conformational control about aryl-C(sp3) bonds in cannabidiol derivatives. Org. Lett. 2019, 21, 6855-6859.

36- Gérard, S.; Bouillon, J.-P; Belaaouaj, A.; Hénon, E. Pyridazin-3-ones fluorées pour leur utilisation dans le traitement des maladies pulmonaires. WO 2016/066973 AI.

37- Barberot, C.; Moniot, A; Allart-Simon, I.; Malleret, L.; Yegorova, T.; Laronze-Cochard, M.; Bentaher A.; Médebielle, M.; Bouillon, J.-P.; Hénon, E.; Sapi, J.; Velard, F.; Gérard, S. Synthesis and biological evaluation of pyridazinone derivatives as potential anti-inflammatory agents. Eur. J. Med. Chem. 2018, 146, 139-146. doi: Réf. HAL: hal-02024470

38- Gérard, S.; Bouillon, J.-P.; Hénon, E.; Sapi, J.; Belaaouaj, A.; Jacquot, J.; Velard, F. Composés de type N-Arylméthyl-4-haloalkyl-pyridazin-3-one et leur utilisation dans le traitement de la mucoviscidose. FR1913404.

39- Cornelio, B.; Laronze-Cochard, M.; Ceruso, M.; Ferraroni, M.; Rance, G. A.; Carta, F.; Khlobystov, A. N.; Fontana, A.; Supuran, C. T.; Sapi, J. 4-Arylbenzenesulfonamides as human carbonic anhydrase inhibitors (hCAIs): synthesis by Pd nanocatalyst-mediated Suzuki-Miyaura reaction, enzyme inhibition, and X-ray crystallographic studies. J. Med. Chem. 2016, 59, 721-732. doi: Réf. HAL: hal-02436454

40- Bhatt, A.; Mahon, B. P.; Cruzeiro, V. W. D.; Cornelio, B.; Laronze-Cochard, M.; Ceruso, M.; Sapi, J.; Rance, G. A.; Khlobystov, A. N.; Fontana, A.; Roitberg, A.; Supuran, C. T.; McKenna, R. Structure-activity relationships of benzenesulfonamide-based inhibitors towards carbonic anhydrase isoform specificity. ChemBioChem 2017, 18, 213-222. doi: Réf. HAL: hal-02436457

41- Ferraroni, M.; Cornelio, B.; Sapi, J.; Supuran, C. T.; Scozzafava, A. Sulfonamide carbonic anhydrase inhibitors: zinc coordination and tail effects influence inhibitory efficacy and selectivity for different isoforms. Inorg. Chim. Acta. 2018, 470, 128-132. doi: Réf. HAL: hal-02436527

42- Cornelio, B.; Laronze-Cochard, M.; Miambo, R.; De Grandis, M.; Riccioni, R.; Borisova, B.; Dontchev, D.; Machado, C.; Ceruso, M.; Fontana, A.; Supuran, C. T.; Sapi, J. 5-Arylisothiazol-3(2H)-one-1,(1)-(di)oxides : a new class of selective tumor-associated carbonic anhydrases (hCA IX and XII) inhibitors. Eur. J. Med. Chem. 2019, 175, 40-48. doi: Réf. HAL: hal-02436497

43- Massicot, F.; Plantier-Royon, R.; Vasse, J.-L.; Behr, J.-B. Synthesis and glycosidase inhibition potency of all-trans substituted 1-C-perfluoroalkyl iminosugars. Carbohydr. Res. 2018, 464, 2-7. doi: Réf. HAL: hal-02429750

44- Résultats non publiés soumis à Eur. J. Org. Chem. (Thèse G. Mérieux, "Nouveaux sulfoniums insaturés : synthèse et évaluation de leurs propriétés d'inhibition de mannosidases", soutenue à Reims le vendredi 21 juin 2019).

45- Bourguet, E.; Brazhnik, K.; Sukhanova, A.; Moroy, G.; Brassart-Pasco, S.; Martin, A.-P.; Villena, I.; Bellon, G.; Sapi, J.; Nabiev, I. Design, synthesis, and use of MMP-2 inhibitor-conjugated quantum dots in functional biochemical assays. Bioconjug. Chem. 2016, 27, 1067-1081. doi: Réf. HAL: hal-01929576

46- Legastelois, R.; Jeanblanc, J.; Vilpoux, C.; Bourguet, E.; Naassila, M. Mécanismes épigénétiques et troubles de l’usage d’alcool : une cible thérapeutique intéressante ? Biologie Aujourd’hui 2017, 211, 83-91. doi: Réf. HAL: hal-01929543

47- Létévé, M.; Gonzalez, C.; Moroy, G.; Martinez, A.; Jeanblanc, J.; Legastelois, R.; Naassila, M.; Sapi, J.; Bourguet, E. Unexpected effect of cyclodepsipeptides bearing a sulfonylhydrazide moiety towards histone deacetylase activity. Bioorg. Chem. 2018, 81, 222-233. doi: Réf. HAL: hal-01929527

48- Bourguet, E.; Ozdarska, K.; Moroy, G.; Jeanblanc, J.; Naassila, M. Class I HDAC inhibitors: potential new epigenetic therapeutics for alcohol use disorder (AUD). J. Med. Chem. 2018, 61, 1745-1766. doi: Réf. HAL: hal-01929517

49- Jeanblanc, J.; Bourguet, E.; Sketriené, D.; Gonzalez, C.; Moroy, G.; Legastelois, R.; Létévé, M.; Trussardi-Régnier, A.; Naassila, M. Interest of new alkylsulfonylhydrazide-type compound in the treatment of alcohol use disorders. Psychopharmacology 2018, 235, 1835-1844. doi: Réf. HAL: hal-01929565

50- Bourguet, E.; Naassila, M. How histone deacetylase (HDAC) activators could be useful leads in the search for new therapeutics? Future Med. Chem. 2019, 11, 1241-1243. doi: Réf. HAL: hal-02429347

51- Linkov, P. A.; Vokhmintcev, K. V.; Samokhvalov, P. S.; Laronze-Cochard, M.; Sapi, J.; Nabiev, I. R. Effect of the semiconductor quantum dot shell structure on fluorescence quenching by acridine ligand. JETP Lett. 2018, 107, 233-237. doi: Réf. HAL: hal-02436466

52- Linkov, P. A.; Vokhmintcev, K. V.; Samokhvalov, P. S.; Laronze-Cochard, M.; Sapi, J.; Nabiev, I. R. The effect of quantum dot shell structure on fluorescence quenching by acridine ligand. KnE Energy 2018, 3, 194-201. doi: Réf. HAL: hal-02436507

53- Allart-Simon, I.; Gérard, S.; Sapi, J. Radical Smiles rearrangement: an update. Molecules 2016, 21, 878-888. doi: Réf. HAL: hal-02436534

54- Menhour B.; Obonou Akong, F.; Mayon, P.; Plé, K.; Bouquillon, S.; Dorey, S.; Clément, C.; Deleu, M.; Harakat, D.; Haudrechy, A. Recycling Mitsunobu coupling: a shortcut for troublesome esterifications. Tetrahedron 2016, 72, 7488-7495. doi: Réf. HAL: hal-01831189

55- Nasir, M. N.; Crowet, J.-M.; Lins, L.; Obonou Akong, F.; Haudrechy, A.; Bouquillon, S.; Deleu, M. Interactions of sugar-based bolaamphiphiles with biomimetic systems of plasma membranes. Biochimie 2016, 130, 23-32. doi: Réf. HAL: hal-01831195

56- Nasir, M. N.; Lins, L.; Crowet, J.-M.; Ongena, M.; Dorey, S.; Dhondt-Cordelier, S.; Clément, C.; Bouquillon, S.; Haudrechy, A.; Sarazin, C.; Fauconnier, M.-L.; Nott, K.; Deleu, M. Differential interaction of synthetic glycolipids with biomimetic plasma membrane lipids correlates with the plant biological response. Langmuir 2017, 33, 9979-9987. doi: Réf. HAL: hal-01831174

57- Luzuriaga-Loaiza, W. P.; Schellenberger, R.; De Gaetano, Y.; Obonou Akong, F.; Villaume, S.; Crouzet, J.; Haudrechy, A.; Baillieul, F.; Clément, C.; Lins, L.; Allais, F.; Ongena, M.; Bouquillon, S.; Deleu, M.; Dorey, S. Synthetic rhamnolipids bolaforms trigger an innate immune response in Arabidopsis thaliana. Sci. Rep. 2018, 8, 8534-8546. doi: Réf. HAL: hal-01831164

58- Lepitre, T.; Denhez, C.; Sanselme, M.; Othman, M.; Lawson, A. M.; Daïch, A. Original Mitsunobu-triggered sequence involved in a one-pot domino process toward tetracyclic systems bearing a bis-N,O-acetal junction. J. Org. Chem. 2016, 81, 8837-8849. doi: Réf. HAL: hal-01928655

59- Lepitre, T.; Denhez, C.; Moncol, J.; Othman, M.; Lawson, A. M.; Daïch, A. Structure-based kinetic control in a domino process: a powerful tool toward molecular diversity in chromone series. J. Org. Chem. 2017, 82, 12188-12201. doi: Réf. HAL: hal-02332616

60- Lefebvre, C.; Rubez, G.; Khartabil, H.; Boisson, J.-C.; Contreras-Garcia, J.; Hénon, E. Accurately extracting the signature of intermolecular interactions present in the NCI plot of the reduced density gradient versus electron density. Phys. Chem. Chem. Phys. 2017, 19, 17928-17936. doi: Réf. HAL: hal-02505160

61- Previtali, V.; Trujillo, C.; Boisson, J.-C.; Khartabil, H.; Hénon, E.; Rozas, I. Development of the first model of a phosphorylated, ATP/Mg2+-containing B-Raf monomer by molecular dynamics simulations: a tool for structure-based design. Phys. Chem. Chem. Phys. 2017, 19, 31177-31185. doi: Réf. HAL: hal-02505102

62- Olea Ulloa, C.; Ponce-Vargas, M.; Munoz-Castro, A. Formation of coinage-metal…fullerene adducts. Evaluation of the interaction nature between triangular coinage metal complexes (M3 = Cu, Ag, and Au) and C60 through relativistic density functional theory calculations. J. Phys. Chem. C. 2018, 122, 25110-25117. doi: Réf. HAL: hal-02429396

63- Hessou, E. P.; Ponce-Vargas, M.; Mensah, J.-B.; Tielens, F.; Santos, J. C.; Badawi, M. Dibenzyl disulfide adsorption on cationic exchanged faujasites: a DFT study. Nanomaterials 2019, 9, 715-724. doi: Réf. HAL: hal-02429391

64- Garcia-Iriepa, C.; Zemmouche, M.; Ponce-Vargas, M.; Navizet, I. The role of solvation models on the computed absorption and emission spectra: the case of fireflies oxyluciferin. Phys. Chem. Chem. Phys. 2019, 21, 4613-4623. doi: Réf. HAL: hal-02429390

65- Kutudila, P.; Linguerri, Ponce-Vargas, M.; Pichon, C.; Condon, S.; Hochlaf, M. Three-phenyl transfer in palladium-catalyzed CC coupling reactions by triarylbismuths: a mechanistic study. Mol. Catal. 2019, 482, 110649-110655. doi: Réf. HAL: hal-02429383

66- Rubez, G.; Etancelin, J.-M.; Vigouroux, X.; Krajecki, M.; Boisson, J.-C.; Hénon, E. GPU accelerated implementation of NCI calculations using promolecular density. J. Comput. Chem. 2017, 38, 1071-1083. doi: Réf. HAL: hal-01497623

67- Lefebvre, C.; Khartabil, H.; Boisson, J.-C.; Contreras-Garcia, J.; Piquemal, J.-P.; Hénon, E. The independent gradient model: a new approach for probing strong and weak interactions in molecules from wave function calculations. Chem. Phys. Chem. 2018, 19, 724-735. doi: Réf. HAL: hal-02126852

68- Ponce-Vargas, M.; Lefebvre, C.; Boisson, J.-C.; Hénon, E. Atomic decomposition scheme of noncovalent interactions applied to host-guest assemblies. J. Chem. Inf. Model. 2020, 60, 1, 268-278. doi: Réf. HAL: hal-02429354

69- Klein, J.; Khartabil, H.; Boisson, J.-C.; Contreras-Garcia, J.; Piquemal, J.-P.; Hénon, E. New Way for Probing Bond Strength. J. Phys. Chem. A 2020, 124, 1850-1860.

Biomolécules : Synthèse et Mécanismes d'Action