Publications depuis 2006

Sous presse

Two-dimensional supramolecular assemblies involving neoglycoplipids: Self-organization and insertion properties into Langmuir monolayers. Y. Queneau, F. Dumoulin, R. Cheaib, S. Chambert, C. Andraud, Y. Bretonnière, L. J. Blum, P. Boullanger, A. Girard-Egrot, Biochimie, sous presse, doi:10.1016/j.biochi.2010.03.009.

Cirsimarin, a potent antilipogenic flavonoid, decreases fat deposition in mice intra-abdominal adipose tissue. B. Zarrouki, N.J. Pillon, E. Kalbacher, H.A. Soula, G. Nia N'jomen, L. Grand, S. Chambert, A. Geloen, C.O. Soulage, Int. J. Obes., sous presse.

Exploitation of Furanoid 5-Azido-3-C-Branched-Chain Sugars Towards  Highly Functionalized Nitrogen-Containing Carbohydrate Derivatives. N. M. Xavier, Y. Queneau, A. P. Rauter, Eur. J. Org. Chem., sous presse.

2010

Carboxymethyl glycoside lactones synthons: scope of the method and preliminary results on polymerization of new glycol-azidoalkynes. J. Chen, Y. Miao, S. Chambert, J. Bernard, E. Fleury, Y. Queneau, Sci. China Chem., 2010, 53, 1880-1887.

Quantitative structure-activity relationship for 4-hydroxy-2-alkenal induced cytotoxicity in L6 muscle cells. N. J. Pillon, L. Soulère, R. E. Vella, M. Croze, B. Caré, H. A. Soula, A. Doutheau, M. Lagarde and C. O. Soulage, Chem-Biol. Interact., 2010, 188, 171-180.

Carbohydrates and sustainable development, Part 1. Renewable resources for chemistry and biotechnology, Eds. A. P. Rauter, Y. Queneau, P. Vogel, Topics in Current Chemistry Vol 294, Springer: Heidelberg, 2010, 200 pages.

Carbohydrates and sustainable development, Part 2. A mine for new synthons and materials Eds. A. P. Rauter, Y. Queneau, P. Vogel, Topics in Current Chemistry, Vol 295,  Springer: Heidelberg, 2010, 200 pages.

(E) Enol Ethers from the Stereoselective Reduction of a-Alkoxy-b-Keto- Phosphonates and Wittig type reaction. W. Dayoub, A. Doutheau, Sci. China Chem., 2010, 53, 1937-1945.

LuxR-dependent quorum sensing: computer aided discovery of new inhibitors structurally unrelated to N-acylhomoserine lactones. L. Soulère, M. Sabbah, F. Fontaine, Y. Queneau, A. Doutheau, Bioorg. Med. Chem. Lett, 2010, 20, 4355-4358.

Neutral Push-Pull Chromophores for Nonlinear Optical Imaging of Cell Membrane. C. Barsu, R. Cheaib, S. Chambert, Y. Queneau, O. Maury, D. Cottet, H. Wege, J. Douady, Y.Bretonnière, and C. Andraud, Org. Biomol. Chem,. 2010, 8, 142-150.

Carbohydrate-based lactones: synthesis and applications. N. M. Xavier, A. P. Rauter, Y. Queneau, in Carbohydrates and sustainable development, Part 2. A mine for new synthons and materials Eds. A. P. Rauter, Y. Queneau, P. Vogel, Topics in Current Chemistry, Vol 295,  Springer: Heidelberg, 2010, 295, 19-62.

Functionalization of carbohydrates in water. M.-C. Scherrmann, A. Lubineau, Y. Queneau, "Handbook of Green Chemistry", P. Anastas, Ed. Volume 5 “Green solvents. Reactions in water”, C. J. Li, Ed., Wiley, 2010, 291-330.

2009

Synthesis of Tetraglucosyl- and Tetrapolyamine-tetrabenzoporphyrin Conjugates for an Application in PDT. F. Ménard, V. Sol, C. Ringot, R. Granet, S. Alves, C. Le Morvan, Y. Queneau, N. Ono, P. Krausz, Bioorg. Med. Chem. 2009, 17, 7647-7657.

Direct azidation of unprotected carbohydrates under Mitsunobu conditions using hydrazoic acid. C. Besset, S. Chambert, B. Fenet, Y. Queneau, Tetrahedron. Lett. 2009, 50, 7043-7047.

The unusual self-organizing behaviour of a glycosteroidal bolaphile. F. Ali Rachedi, S. Chambert, F. Ferkous, Y. Queneau, S. J. Cowling, J. W. Goodby, Chem. Commun., 2009, 6355-6357.

Le saccharose et l'isomaltulose: deux exemples de sucres pour la synthèse de dérivés fonctionnels ou de synthons pour la chimie fine. Y. Queneau, L'Actualité Chimique, 2009, n°334, 36-40.

Enantioselective Synthesis of the R-Enantiomer of the Feeding Deterrent (S)-Ypaoamide. J. Chen, P. Q. Huang, Y. Queneau, J. Org. Chem., 2009, 74, 7457-7463.

2,2'-Bipyridine-3,3'-dicarboxylic carbohydrate esters and amides. Synthesis and preliminary evaluation as ligands in Cu(II) catalysed enantioselective electrophilic fluorination. A. Assalit, T. Billard, S. Chambert, B. R. Langlois, Y. Queneau, D. Coe, Tetrahedron Asymmetry, 2009, 20, 593-601.

Design, solid phase synthesis and evaluation of cationic ferrocenoyl peptide bioconjugates as potential antioxidant enzyme mimics. L. Soulère, J. Bernard, Bioorg. Med. Chem. Lett., 2009, 19; 1173-1176.

Toward docking based virtual screening for discovering antitubulin agents by targeting taxane and colchicine binding sites. L. Soulère, ChemMedChem, 2009, 4, 161-163.

Cell Wall Polysaccharide Synthases are Located in Detergent Resistant Membrane Microdomains in Oomycetes. Briolay, A.; Bouzenzana, J.; Guichardant, M.; Deshayes, C.; Sindt, N.; Bessueille, L.; Bulone, V. Appl. Environ. Microbiol. 2009, 75, 1938–1949.

Glycosidic bicyclic lactones as new carbohydrate scaffolds. Y. Queneau, S. Chambert, S. Moebs, A. Listkowski, R. Cheaib, Carbohydrate Chemistry – Chemical and Biological Approaches, A. P. Rauter and T. K. Lindhorst, Eds, 2009, 35, 99-126.

2008

AHL communication is a widespread phenomenon in biomining bacteria and seems to be involved in mineral-adhesion efficiency . L. M. Rui, M. Castro, S. Valenzuela, A. Gonzalez, M. Frezza, L. Soulère, Y. Queneau, A. Doutheau, T. Rohrwerder, W. Sand, C. A. Jerez, N. Giuliani, Hydrometallurgy 2008, 94, 133-137.

Synthesis of New Mono- and Disaccharidic Carboxymethylglycoside Lactones (CMGLs) and Their Use For Obtaining 1,2-Bis-Functionalized Carbohydrates Synthons. R. Cheaib, A. Listkowski, S. Chambert, A. Doutheau, Y. Queneau, Tetrahedron: Asymmetry 2008, 19, 1919-1933.

N-acyl-3-amino-5H-furanone derivatives as new inhibitors of LuxR-dependent quorum sensing: synthesis, biological evaluation and binding mode study. J. Estephane, J. Dauvergne, L. Soulère, S. Reverchon, Y. Queneau, A. Doutheau, Bioorg. Med. Chem. Lett . 2008, 18, 4321-4324.

Recent progress in the synthesis of carbohydrate-based amphiphilic materials: the examples of sucrose and isomaltulose. Y. Queneau, S. Chambert, C. Besset, R. Cheaib, Carbohydr. Res. 2008, 343, 1999-2009.

Molecular insights into quorum sensing in Acidithiobacillus ferrooxidans bacteria through a molecular modelling study of the transcriptional regulator AfeR and of the binding mode of long-chain acyl homoserine lactones. L. Soulère, N. Guiliani, Y. Queneau, C. A. Jerez, A. Doutheau, J. Molecular Model., 2008, 14, 599-606.

Synthetic homoserine lactone derived sulfonyl ureas as Inhibitors of Vibrio fischeri Quorum Sensing regulator. M. Frezza, L. Soulère, S. Reverchon, N. Guiliani, C. Jerez, Y. Queneau, A. Doutheau, Bioorg. Med. Chem, 2008, 16, 3550-3556.

Reactivity of melezitose and raffinose under Mitsunobu esterification conditions. C. Besset, S. Chambert, Y. Queneau, S. Kerverdo, H. Rolland, J. Guilbot, Carbohydr. Res. 2008, 343, 929-935.

Carboxymethyl Glucoside and Carboxymethyl Glucoside Lactones: a Detailed Study on their Preparation by Oxidative Degradation of Disaccharides. R. Pierre, S. Chambert, F. Alirachedi, M. Danel, S. Trombotto, A. Doutheau, Y. Queneau, C. R. Chimie, 2008, 11, 61-66.

Sucrose chemistry and applications of sucrochemicals. Y. Queneau, S. Jarosz, B. Lewandowski, J. Fitremann, Adv. Carbohydr. Chem. Biochem., 2008, 61, 217-292.

Method for preparing acetyl-docosahexaenoyl-glycerophosphocholine and use thereof for the delivery of polyunsaturated fatty acids. M. Lagarde, M. Guichardant, M. Picq, S. Michaud, A. Doutheau, PCT Int. Appl.  (2008) WO  2008068413

2007

Thermotropic Liquid Crystalline Glycolipids, J.W. Goodby, V. Görtz, S. J. Cowling, G. Mackenzie, P. Martin, D. Plusquellec, T. Benvegnu, P. Boullanger, D. Lafont, Y. Queneau, S. Chambert, J. Fitremann, Chem. Soc. Rev., 2007, 36, 1971-2032.

Carboxymethylglycoside Lactones (CMGLs): Structural Variations on the Carbohydrate Moiety. A. Listkowski, P. Ing, R. Cheaib, S. Chambert, A. Doutheau, Y. Queneau, Tetrahedron: Asymmetry, 2007, 18, 2201-2210.

An expeditious synthesis of 4-hydroxy-2(E)-nonenal (4-HNE), its dimethyl acetal and of related compounds. L. Soulère, Y. Queneau and A. Doutheau, Chem. Phys. Lipids, 2007, 150, 239-243.

Exploring the active site of acyl homoserine lactones-dependent transcriptional regulators with bacterial quorum sensing  modulators using molecular mechanics and docking studies. L. Soulère, M. Frezza, A. Doutheau, Y. Queneau, J. Mol. Graph. Model., 2007, 26, 581-590.

Preparation of 6,6,1',1',6',6'-hexadeutero sucrose. M.-H. Gouy, M. Danel, M. Gayral, A. Bouchu, Y. Queneau, Carbohydr. Res., 2007, 342, 2303-2308.

Co-melting of solid sucrose and multivalent cation soaps for solvent-free synthesis of sucrose esters. J. Fitremann, Y. Queneau, J. P. Maitre, A. Bouchu, Tetrahedron Lett. 2007, 48, 4111-4114.

Synthesis and thermotropic behaviour of simple new glucolipide amides, S. Chambert, S. J. Cowling, G. Mackenzie, J. W. Goodby, A. Doutheau, Y. Queneau, J. Carbohydr. Chem. 2007, 26, 27-39.

Evidence for in situ ethanolamine phospholipid adducts with hydroxy-alkenals. S. Bacot, N. Bernoud-Hubac, B. Chantegrel, C. Deshayes, A. Doutheau, G. Ponsin, M. Lagarde, M. Guichardant, J. Lipid. Res., 2007, 48, 816-825.

Ac2-DPD, the bis-(O)-acetylated derivative of 4,5-dihydroxy-2,3-pentanedione (DPD) is a convenient stable precursor of quorum sensing autoinducer AI-2. M. Frezza, L. Soulère, D. Balestrino, Y. Queneau, C. Forestier, A.Doutheau, Bioorg. Med. Chem. Lett., 2007, 17, 1428-1431.

Shape dependence in the formation of condensed phases exhibited by disubstituted sucrose esters. V. Molinier, P.H. Kouwer, J. Fitremann, A. Bouchu, G. Mackenzie, Y. Queneau, et J. W. Goodby, Chem. Eur. J., 2007, 13, 1763-1775.

Membrane properties of dipalmitoyl bis(monoaclyglycero)phosphate. T. Hayakawa, A. Makino, S. Michaud, M. Lagarde, A. Doutheau, K. Ito, M. Hirai, T. Kobayashi, Maku (Membrane), 2007, 32, 221-228.

2006

Highly Wolff selective Rh(II) catalysed decomposition of a -diazo-b-ketophosphonates having an oxygen atom adjacent to the  -position. M. Boukraa, W. Dayoub et A. Doutheau, Lett. Org. Chem., 3, 2006, 204-206.

Preparation of amide-linked pseudo-disaccharides by the carboxymethylglycoside lactone (CMGL) strategy. A. Le Chevalier, R. Pierre, S. Chambert, A. Doutheau, Y. Queneau, Tetrahedron Lett., 2006, 47, 2431-2434.

Self-organizing Properties of Monosubstituted Sucrose Fatty Acid Esters: The Effects of Chain Length and Unsaturation. V. Molinier, P.H. Kouwer, J. Fitremann, A. Bouchu, G. Mackenzie, Y. Queneau, et J. W. Goodby, Chem. Eur. J., 2006, 12, 3547-3557.

Synthesis and biological evaluation of homoserine lactone derived ureas as antagonists of bacterial quorum sensing. M. Frezza, S. Castang, J. Estephane, L. Soulère, C. Deshayes,  B. Chantegrel, W. Nasser, Y. Queneau, S. Reverchon, A. Doutheau, Bioorg. Med. Chem., 2006, 14, 4781-4791.

Concentration measurements of sucrose and sugar surfactants solutions by using the 1H NMR ERETIC method. V. Molinier, B. Fenet, J. Fitremann, A. Bouchu, Y. Queneau, Carbohydr. Res., 2006, 341, 1890-1895.

Synthesis of new glycosylated porphyrins bearing an a-D linkage. V. Sol, A. Charmot, S. Trombotto, Y. Queneau, P. Krausz, J. Carbohydr. Chem., 2006, 25, 345-360.

Selective synthesis of amphiphilic hydroxyalkylethers of disaccharides over solid basic catalysts. Influence of the superficial hydrophilic-lipophilic balance of the catalyst. N. Villandier, I. Adam, F. Jérôme, J. Barrault, R. Pierre, A. Bouchu, J. Fitremann, Y. Queneau, J. Mol. Catal. A, 2006, 259, 67-77.

Differential membrane packing of stereoisomer of bis(monoacylglycero)phosphate. T. Hayakawa, Y. Hirano, A. Makino, S. Michaud, M. Lagarde, J.-F. Pageaux, A. Doutheau, K. Ito, T. Fujisawa, H. Takahashi, T. Kobayashi, Biochemistry, 2006, 45, 9198-9209.

Synthesis and biological evaluation of the trifluoromethyl analog of (4S)-4,5-dihydroxy-2,3-pentanedione (DPD). M. Frezza, D. Balestrino, L. Soulère, S. Reverchon-Pescheux, Y. Queneau, C. Forestier, A. Doutheau, Eur. J. Org. Chem., 2006, 4731-4736.

Conjugated linoleic acid, unlike other unsaturated fatty acids, strongly induces glutathione synthesis without any lipoperoxidation. K. Arab, A. Rossary, L. Soulère, J-P Steghens, British Journal of Nutrition, 2006, 96, 811-819.

Synthetic Studies on the MARDI Cascade : Stereoselective Synthesis of Heterocyclic Seven-Membered Rings Y. Coquerel, D. Bensa, A. Doutheau, J. Rodriguez. Org. Lett. , 2006, 8, 4819-4822.

La Sucrochimie. Y. Queneau et J. Fitremann, dans Chimie Verte, P. Colonna, Ed., Tech & Doc Lavoisier, Paris, 2006, 239-270.

Carboxymethyl tri-O-acetyl-a-D-glucopyranoside lactone: a synthon for the preparation of pseudo glycoconjugates. Y. Queneau, S. Chambert, R. Cheaib, A. Listkowski, A. Doutheau, S. Trombotto, Targets in Heterocyclic Systems – Chemistry and Properties, O. A. Attanasi and D. Spinelli, Eds., Italian Society of Chemistry: Rome, Vol. 10 (2006), p. 132-151.

Procédé de prépartion d’acetyl, docosahexaenoyl-glycerophosphocholine, et son utilisation pour l’apport d’acide gras polyinsaturés. M. Picq, S. Michaud, A. Doutheau, M. Guichardant, M. Lagarde. Brevet français déposé N° 06/09929 le 14/11/2006  A 20061114.