Laboratoire des Glucides

FRE 3517

Accueil > Équipe SUPRA >Cyrille Grandjean

Florence Djédaïni-PilardChargé de Recherche CNRS (HDR)
Mail : cyrille.grandjean@u-picardie.fr
Tel : 03 22 82 88 12
Fax : 03 22 82 75 60
C.V.

 

Membre de l'équipe SUPRA

Description des travaux de recherche

Les motifs sucres exprimés au sein ou à la surface de nos cellules ou des microorganismes sont impliqués dans un grand nombre d'interactions intracellulaires ainsi que cellule-cellule, cellule-matrice ou hôte-pathogène. Ils interviennent, entre autres, dans les processus de fécondation, d'embryogénèse, de développement neuronal, d'activités hormonales, de localisation cellulaire de glycoprotéines, de régulation d'expression de gènes, de prolifération cellulaire, d'organisation des cellules en tissu, de réactions inflammatoires, de surveillance par le système immunitaire. L'étude de ces motifs sucres et de leur reconnaissance par leurs différents récepteurs est indispensable pour élucider leur fonctions biologiques ainsi que prévenir ou soigner des pathologies dues à la présence, l'absence ou l'altération d'un de ces motifs.
Deux aspects sont actuellement abordés :

Publications

  • Vibrio cholerae LPS detoxified derivatives and immunogenic compositions.
    C. GRANDJEAN, L. MULARD.
    Can. Pat. Appl., 2006, 48 pp. CODEN: CPXXEB CA 2475736 A1 20060123 Application: CA 2004-2475736 20040723.
  • Characterization of functional oligosaccharide mimics of the Shigella flexneri serotype 2a O-antigen: implications for the development of a chemically defined glycoconjugate vaccine.
    A. PHALIPON, C. COSTACHEL, C. GRANDJEAN, A. THUIZAT, C. GUERREIRO, M. TANGUY, F. NATO, B. VULLIEZ-LE NORMAND, F. BELOT, K. WRIGHT, V. MARCEL-PEYRE, P. J. SANSONETTI, L. MULARD.
    Journal of immunology, 2006, 176(3), 1686-94.
  • (Diphenylphosphino)methanethiol.
    C. GRANDJEAN, D. BONNET.
    Electronic Encyclopedia of Reagents for Organic Synthesis, 2006.
  • Effect of glycoamphiphiles on the solubilization and dendritic cell uptake of a lipopeptide: a preliminary study.
    D. BONNET, G. ANGYALOSI, A. DEMORY, V. SANTRAINE, A. BOULET, C. SPRIET, L. HELIOT, H. GRAS-MASSE, C. GRANDJEAN.
    Molecular pharmaceutics, 2005, 2(5), 420-7.
  • On the preparation of carbohydrate-protein conjugates using the traceless Staudinger ligation.
    C. GRANDJEAN, A. BOUTONNIER, C. GUERREIRO, J.-M. FOURNIER, L. A.  MULARD.
    The Journal of organic chemistry, 2005, 70(18), 7123-32.
  • Anchorage of synthetic peptides onto liposomes via hydrazone and alpha-oxo hydrazone bonds. preliminary functional investigations.
    L. BOUREL-BONNET, E. I. PECHEUR, C. GRANDJEAN, A. BLANPAIN, T. BAUST, O. MELNYK, B. HOFLACK, H. GRAS-MASSE.
    Bioconjugate chemistry, 2005, 16(2), 450-7.
  • Efficient  preparation  of  carbohydrate  and  related  polyol-amphiphiles  by  hydrazone ligation.
    C. GRANDJEAN, V. SANTRAINE, N. FARDEL, A. POLIDORI, B. PUCCI, H. GRAS-MASSE, D. BONNET.
    Tetrahedron Lett., 2004, 45, 3451-3454.
  • Solid-phase functionalization of peptides by an α-hydrazinoacetyl group.
    D. BONNET, C. GRANDJEAN, P. ROUSSELOT-PAILLEY, P. JOLY, L. BOUREL-BONNET, V. SANTRAINE, H. GRAS-MASSE, O. MELNYK.
    The Journal of organic chemistry, 2003, 68(18), 7033-40.
  • Grafting of synthetic mannose receptor-ligands onto onion vectors for human dendritic cells targeting.
    P. CHENEVIER, C. GRANDJEAN, E. LOING, F. MALINGUE, G. ANGYALOSI, H. GRAS-MASSE, D. ROUX, O. MELNYK, L. BOUREL-BONNET.
    Chemical Communications, 2002, (20), 2446-2447.
  • Synthesis and mannose receptor-mediated uptake of clustered glycomimetics by human dendritic cells: effect of charge.
    G. ANGYALOSI, C. GRANDJEAN, M. LAMIRAND, C. AURIAULT, H. GRAS-MASSE, O. MELNYK.
    Bioorganic & Medicinal Chemistry Letters, 2002, 12(19), 2723-2727.
  • Combined Thioether/Hydrazone Chemoselective Ligation Reactions for the Synthesis of Glycocluster-Antigen Peptide Conjugates.
    C. GRANDJEAN, V.  SANTRAINE, J.-S. FRUCHART, O.  MELNYK, H.  GRAS-MASSE.
    Bioconjugate Chemistry, 2002, 13(4), 887-892.
  • Synthesis of clustered glycoside-antigen conjugates by two one-pot, orthogonal, chemoselective ligation reactions: scope and limitations.
    C. GRANDJEAN, O.  MELNYK, H.  GRAS-MASSE.
    Chemistry, 2001, 7(1), 230-9.
  • Novel hyperbranched glycomimetics recognized by the human mannose receptor: quinic or shikimic acid derivatives as mannose bioisosteres.
    C. GRANDJEAN, G. ANGYALOSI, E.  LOING, E. ADRIAENSSENS, O. MELNYK, V. PANCRE, C. AURIAULT, H. GRAS-MASSE.
    ChemBioChem, 2001, 2(10), 747-757.
  • Tartaric Acid-Based Linker for the Solid-Phase Synthesis of C-Terminal Peptide α-Oxo Aldehydes.
    O. MELNYK, J.-S. FRUCHART, C. GRANDJEAN, H. GRAS-MASSE.
    Journal of Organic Chemistry, 2001, 66(12), 4153-4160.
  • Use of quinic, shikimic acids and their derivatives for preparing mannose receptor ligands.
    C. GRANDJEAN, O. MELNYK, H. GRAS-MASSE, G. ANGYALOSI, C. ROMMENS, C. AURIAULT.
    PCT Int. Appl., 2001, 86 pp. Application: WO 2000-FR2194 20000728. FR 99-9928 19990730.
  • Synthesis of clustered glycoside - antigen conjugates by two one-pot, orthogonal, chemoselective ligation reactions: scope and limitations.
    C. GRANDJEAN, H. GRAS-MASSE, O. MELNYK.
    Chemistry--A European Journal, 2001, 7(1), 230-239.
  • One-pot synthesis of antigen-bearing, lysine-based cluster mannosides using two orthogonal chemoselective ligation reactions.
    C. GRANDJEAN, C. ROMMENS, H. GRAS-MASSE, O. MELNYK.
    Angewandte Chemie, International Edition, 2000, 39(6), 1068-1072.
  • Convergent synthesis of D-(-)-quinic and shikimic acid-containing dendrimers as potential C-lectin ligands by sulfide ligation of unprotected fragments.
    C. GRANDJEAN, C. ROMMENS, H. GRAS-MASSE, O. MELNYK.
    Organic and Bio-Organic Chemistry, 1999, (20), 2967-2975.
  • Synthesis and Biological Activity of Natural Aminocyclopentitol Glycosidase Inhibitors: Mannostatins, Trehazolin, Allosamidins, and Their Analogs.
    A. BERECIBAR, C. GRANDJEAN, A. SIRIWARDENA.
    Chemical Reviews, 1999, 99(3), 779-844.
  • Convergent synthesis of fluorescein-labeled lysine-based cluster glycosides.
    C. GRANDJEAN, C. ROMMENS, H. GRAS-MASSE, O. MELNYK.
    Tetrahedron Letters, 1999, 40(40), 7235-7238.
  • Synthesis of the two monomethyl esters of the disaccharide 4-O-α-D-galacturonosyl-D-galacturonic acid and of precursors for the preparation of higher oligomers methyl uronated in definite sequences.
    D. MAGAUD, C. GRANDJEAN, A. DOUTHEAU, D. ANKER, V. SHEVCHIK, N. COTTE-PATTAT, J. ROBERT-BAUDOUY.
    Carbohydrate Research, 1998, 314(3-4), 189-199.
  • An efficient and highly stereoselective α(1-4) glycosylation between two D-galacturonic acid ester derivatives.
    D. MAGAUD, C. GRANDJEAN, A. DOUTHEAU, D. ANKER, V. SHEVCHIK, N. COTTE-PATTAT, J. ROBERT-BAUDOUY.
    Tetrahedron Letters, 1997, 38(2), 241-244.
  • Preparation and in vitro antibacterial activity of 9-O-glycosyloxime derivatives of erythromycin A, a new class of macrolide antibiotics.
    C. GRANDJEAN, G. LUKACS.
    Journal of Antibiotics, 1996, 49(10), 1036-1043.
  • SN2 displacement of carbohydrate triflates by 9-oximes of erythromycin A and of a tylosin derivative.
    C. GRANDJEAN, G. LUKACS.
    Journal of Carbohydrate Chemistry, 1996, 15(7), 831-855.
  • Synthesis of 4'-oxo-demycarosyl-3-O-(α -L-rhamnopyranosyl)tylosin.
    C. GRANDJEAN, G. LUKACS.
    Bulletin de la Societe Chimique de France, 1995, 132(11), 1145-8.
  • Trisubstituted benzoate synthesis via carbopalladation of allenes.
    V. GAUTHIER, C. GRANDJEAN, B. CAZES, J. GORE.
    Bulletin de la Societe Chimique de France, 1994, 131(4), 381-90.
  • Carbopalladation of functionalized allenes: regioselectivity of the reaction of carbonucleophiles with the intermediate p -allyl palladium complexes.
    N. CHAPTAL, V. COLOVRAY-GOTTELAND, C. GRANDJEAN, B. CAZES, J. GORE.
    Tetrahedron Letters, 1991, 32(15), 1795-8.
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