CURRICULUM VITAE GUICHARD Gilles 40 years, French, CNRS Research Director (since 2006) POSITIONS

>From September 2009 to present: Group Leader - Institut Européen de Chimie et Biologie (IECB) – CBMN, CNRS UMR 5248 Université de Bordeaux I –Pessac, France. >From October 2006 to August 2009: Directeur de Recherche CNRS - CNRS UPR 9021 – Immunologie et Chimie Thérapeutiques CNRS UPR 9021– Institut de Biologie et Moléculaire et Cellulaire (IBMC) - Strasbourg France. >From 1998-september 2006 : Chargé de recherché CNRS - CNRS UPR 9021 – Immunologie et Chimie Thérapeutiques – CNRS UPR 9021 - Institut de Biologie et Moléculaire et Cellulaire (IBMC) - Strasbourg France. Research interests: non-natural folding oligomers –Foldamers - as proteomimetics (chemistry, structure and (bio)molecular recognition), multivalency in drug design for targeting protein/protein interactions (application to the design of TNF mimetics), peptidomimetic and combinatorial chemistry EDUCATION/TRAINING Ecole Nationale Supérieure de Chimie, Toulouse, France Strathclyde University, Glasgow UK2 Montpellier University, France, Master (DEA)2 Strasbourg University (ULP), France, PhD (superv. Dr J.P. Briand) ETH Zürich (Switzerland), Post-doc by Prof D. Seebach

1988-1991 1990-1991 1992 1996 1997-1998

Chemistry Chemistry Chem. Biol. Chem. Biol Chemistry

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as part of the European Credit Transfer System (ECTS) : European Community Program for student exchange 2 DEA = Diplôme d’étude Approfondie = Master degree OTHER EXPERIENCE AND PROFESSIONAL MEMBERSHIPS : > Co-founder of ImmuPharma France http://www.immupharma.com/index.html (a small drug discovery and development company focused on developing novel, largely peptide, medicines to treat serious medical conditions). > President of the « Groupe Français des Peptides et des Protéines » (GFPP) (2007-2009) > Organizer of the 16th GFPP Meeting (May 10-15th 2009, Albé, France). http://gfpp.free.fr/ > Management Committee Substitute Member of COST action CM0803:Functional peptidomimetic foldamers (end date 2012) HONORS Bronze medal of the CNRS in 2000. PUBLICATIONS 87 publications in journals with peer review, 4 book chapters , 16 patents, H-factor = 24

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PUBLICATIONS in Peer review

2010 87

Fischer L, Guichard G. Folding and self-assembly of aromatic and aliphatic urea oligomers: Towards connecting structure and function. Org Biomol Chem. 2010, ASAP. [Perspective Article]

86

Ejsmont K, Boeglin J, Didierjean C, Guichard G, Jelsch C. 5-(3,4-Dimethoxybenzyl)-7-isopropyl1,3,5-triazepane-2,6-dione acetonitrile solvate refined using a multipolar atom model. Acta Crystallogr C. 2010, o292-294.

*85

Pavet, V.; Beyrath, J.; Pardin, C.; Morizot, A.; Lechner, M.-C.; Briand, J.-P.; Wendland, M.; Maison, W.; Fournel, S.; Micheau, O.; Guichard, G.; Gronemeyer, H. Multivalent DR5-selective peptides activate the TRAIL death pathway and exert tumoricidal activity in vivo. Cancer Res. 2010, 70, 1101-10.

*84

Fischer, L.; Claudon, P.; Pendem, N.; Miclet, E.; Didierjean, C.; Ennifar, E.; Guichard, G. The Canonical Helix of Urea Oligomers at Atomic Resolution. Insight Into Folding-induced Axial Organization. Angew. Chem. Int. Ed. Engl. 2010, 49, 1067-70.

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Claudon, P.; Violette, A.; Lamour, K.; Decossas, M.; Fournel, S.; Heurtault, B.; Godet, J.; Mély, Y.; Jamart-Grégoire, B.; Averlant-Petit, M.-C.; Briand, J.-P.; Duportail, G.; Monteil, H.; Guichard, G. Consequences of Isostructural Main-Chain Modifications for the Design of Antimicrobial Foldamers: Helical Mimics of Host-Defense Peptides Based on a Heterogeneous Amide/Urea Backbone. Angew. Chem. Int. Ed. Engl. 2010, 49, 333-6.

2009 82

Hennig, A.; Fischer, L.; Guichard, G.; Matile, S. Anion-Macrodipole Interactions: Self-Assembling Oligourea/Amide Macrocycles as Anion Transporters that Respond to Membrane Polarization. J. Am. Chem. Soc. 2009, 131, 16889-16895.

81

Mocquet, C.; Salaun, A.; Claudon, P.; Grel, B. L.; Potel, M.; Guichard, G.; Jamart-Grégoire, B.; Le Grel, P. Aza-beta3-cyclopeptides: A New Way of Controlling Nitrogen Chirality. J. Am. Chem. Soc. 2009, 131, 14521-14525.

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L. Fischer, M. Decossas, J.-P. Briand, C. Didierjean, G. Guichard. Control of Duplex Formation and Columnar Self-assembly With Heterogeneous Amide/urea Macrocycles. Angew. Chem. Int . Ed. 2009, 48, 1625-1628.

2008 79

G. Guichard, A. Violette, G. Chassaing, E. Miclet*. Solution Structure Determination of Oligoureas Using Methylene Spin State Selective NMR at 13C Natural Abundance. Magn. Reson. Chem.2008, 46, 918-924. DOI: 10.1002/mrc.2271.

78

M.C. Lechner, E. Aubert, G. Guichard, C. Didierjean. tert-Butyl 3-oxo-2-oxa-5azabicyclo[2.2.1]heptane-5-carboxylate. Acta Cryst. 2008. E64, o2039.

77

G. Léna, G. Guichard*, Synthetic methods for the preparation of triazepandiones and review of their applications. Curr. Org. Chem. 2008, 12, 813-835

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D. Destouches, D. El Khoury, Y. Hamma-Kourbali1, B. Krust, P. Albanese1, P. Katsoris, G. Guichard, J. P. Briand, J. Courty, A. G. Hovanessian. Suppression of Tumor Growth and Angiogenesis by a Specific Antagonist of the Cell-Surface Expressed Nucleolin, PloS ONE, 2008, 3, e2518.

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L. Fischer C. Didierjean, F. Jolibois, V. Semetey, J. M. Lozano, J. P. Briand, M. Marraud R. Poteau G. Guichard*, Propensity for local folding induced by the urea fragment in short chain oligomers. Org. Biol. Chem. 2008, 6, 2596–2610.

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A. Violette, N. Lancelot, A. Poschalko, M. Piotto, J. P. Briand, J. Raya, K. Elbayed. A. Bianco, G. Guichard*, Exploring helical folding of oligoureas during chain elongation by HRMAS NMR. Chem. Eur. J. 2008, 14, 3874-3882.

73

O. Chaloin, F. Cabart, J. Marin, H Zhang, Guichard, G.* Synthesis of enantiopure di(tert-butyl) (2S,4S)-4-hydroxy-6-oxo-1,2,-piperidinedicarboxylate. Org. Synth. 2008 85, 147-157

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J. Marin, J.-P. Briand,, G. Guichard*, Synthesis of a Galactosylated 4-Hydroxylysine Building Block and Incorporation in a Collagen Immunodominant Glycopeptide. Eur. J. Org. 2008 10051012.

2007 *71

Trouche, N., Wieckowski, S., Sun, W., Chaloin, O., Hoebeke, J., Fournel, S.* & Guichard, G.* Small Multivalent Architectures Mimicking Homotrimers of the TNF Superfamily Member CD40L: Delineating the Relationship between Structure and Effector Function. J. Am. Chem. Soc. 2007, 129,13480-92.

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Glatigny S., Blaton MA., Marin J., Mistou S., Guichard G., Fournier C. and Chiocchia G. Insights into spatial configuration of a galactosylated epitope required to trigger arthritogenic T cells receptors specific for the sugar moiety. Arthritis Res. Ther. 2007, 9, R92

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M. Habib, M. Chamekh , M. Noval Rivas, S. Wieckowski, W. Sun, A. Bianco, N. Trouche, O. Chaloin, H. Dumortier, M. Goldman G. Guichard, S. Fournel*, and Bernard Vray*. Cutting Edge : Small molecule CD40L mimetics promote control of parasitemia and enhance CD8+ T cells producing interferon-γ during experimental Trypanosoma cruzi infection J. Immunol, 2007, 178, 6700-6704.

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E. Aubert, G. Lena, M. Gellenoncourt, E. Durain, G. Guichard*, C. Didierjean. 7-Isopropyl-5-methyl1,3,5-triazepan-2,6-dione deuterated chloroform 0.94-solvate. Acta Cryst., 2007, E63, o2306– o2308

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Fischer L., Semetey V., Lozano J.M., Schaffner A.P., Briand J.P., Didierjean C., Guichard G*. Succinimidyl Carbamate Derivatives from N-protected alpha-Amino Acids and Dipeptides. Synthesis of Ureidopeptides and Oligourea/peptide Hybrids. Eur. J. Org. Chem. 2007, 2511–2525.

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M. T. Oakley, G. Guichard, J. D. Hirst*. Calculations on the Electronic Excited States of Ureas and Oligoureas. J. Phys. Chem. B, 2007, 111, 3274-3279.

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Wieckowski, S.; Trouche, N.; Chaloin, O.; Guichard, G.; Fournel, S.*; Hoebeke, J*. Cooperativity in the interaction of synthetic CD40L mimetics with CD40 and its implication in cell signalling. Biochemistry, 2007, 46, 3482-3493.

2006 *64

P. Muller, G. Lena, S. Bezzine, E. Boilard, M. Lazdunski, G. Lambeau, G. Guichard, D. Rognan*. In silico-guided target identification of a scaffold-focussed library: 1,3,5-Triazepane-2,6-dione as novel phospholipase A2 inhibitors J. Med. Chem.2006, 49, 6768 - 6778; (DOI:10.1021/jm0606589)

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A.-P. Schaffner, G. Lena, S. Roussel, A. Wawrezinieck, A. Aubry, J.-P. Briand, C. Didierjean, and G. Guichard*. Porous 3D-Honeycomb architecture by self-assembly of helical H-bonded molecular tapes. Chem. Commun., 2006, 469-471.(DOI:10.1039/B604747E). Within top ten most accessed ChemComm articles in the month of October

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G. Lena, E. Lallemand, A. C. Gruner, J. Boeglin, S. Roussel, A.-P. Schaffner, A. Aubry, J.-F. Franetich, D. Mazier, I. Landau, J.-P. Briand, C. Didierjean, L. Rénia*, G. Guichard*. 1,3,5Triazepan-2,6-diones as Structurally Diverse and Conformationally Constrained Dipeptide Mimetics. Identification of Malaria Liver Stage Inhibitors From a Small Pilot Library. Chem Eur. J. 2006, 12, 8498-512. DOI : 10.1002/chem.200600560.

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A. Violette, Sylvie Fournel, K. Lamour, O. Chaloin, B. Frisch, J.-P. Briand, H. Monteil, G. Guichard*. Mimicking helical antibacterial peptides with non-peptidic folding oligomers. Chem. Biol., 2006, 13, 531-538. (doi:10.1016/j.chembiol.2006.03.009)

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A. Bianco,* S. Fournel, S. Wieckowski, J. Hoebeke, and G. Guichard* Solid-phase synthesis of CD40L mimetics, Org. Biol. Chem. 2006, 4, 1461-1463. (doi : 10.1039/b601528j).

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G. Lena, E. Wenger, G. Guichard,* C. Didierjean.* 10-methyl-8,9,10,11,11a,12-hexahydro-5H,7Hisoquinolino[3,2-g][1,3,5]triazepine-7,11-dione. Acta Cryst., 2006, E62, o518-o520

2005 58

S. Fournel*, S. Wieckowski, W. Sun, N. Trouche, H. Dumortier, A. Bianco, O. Chaloin, M. Habib, J.C. Peter, P. Schneider, B. Vray, R. E. Toes, R. Offringa, C. J. M. Melief, J. Hoebeke, G. Guichard*. C3-symmetric peptide scaffolds are functional mimetics of trimeric CD40L. Nature Chem. Biol. 2005 1, 377-382.. (doi : 10.1038/nchembio746).

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J. Marin, M.-A. Blaton, Jean-Paul Briand, G. Chiocchia, C. Fournier*, G. Guichard*, Synthesis of glycopeptides from Type II Collagen incorporating galactosylated hydroxylysine mimetics and their use to study the fine specificity of arthritogenic T cells. ChemBioChem 2005, 6, 1796-1804 (doi : 10.1002/cbic.200500075)

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A. Violette, M. C. Averlant-Petit, V. Semetey,C. Hemmerlin, R. Casimir, R. Graff, M. Marraud, J.-P. Briand, D. Rognan, and G. Guichard*. N,N’-Linked Oligoureas as Foldamers : Chain Length Requirements for Helix Formation in Protic Solvent Investigated by Circular Dichroism, NMR Spectroscopy and Molecular Dynamics. J. Am. Chem.Soc. 2005, 127, 2156-2164 (doi : 10.1021/ja044392b)

2004 55

A. Poschalko, N. Lancelot, J. Marin, V. Larras, D. Limal, K. Elbayed, J. Raya, M. Piotto, J.-P. Briand, G. Guichard*, A. Bianco*. DEUSS: a Perdeuterated Polyoxyethylene-based Resin for Improving HRMAS NMR Study of Solid-supported Molecules. Chem. Eur. J. 2004, 10, 4532-4537

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J. Marin, A. Violette, J. –P. Briand, and G. Guichard*, Galactosylated 5-Hydroxylysine Mimetics for Glycopeptide Synthesis. Eur. J. Org. Chem., 2004, 3027-3039.

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C. Didierjean, J. Marin, E. Wenger, J.-P. Briand, A. Aubry*, G. Guichard. (6S)-6-Isobutyl-2,4-dioxopiperidine and (4R,6S)-4-Hydroxy-6-isobutyl-2-oxo-piperidine. Acta Cryst. 2004, C60, o204-o207

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C. Didierjean, J. Marin, E. Wenger, J.-P. Briand, A. Aubry*, G. Guichard. tert-butyl-(6R)-4Hydroxy-6-isobutyl-2-oxo-2,5-dihydro-(2H)-pyridine-carboxylate and tert-butyl-(4S,6R)-4Hydroxy-6-isobutyl-2-oxo-1-piperidine-carboxylate. Acta Cryst. 2004 C60, o200-o203

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J. Marin, C. Didierjean, A. Aubry, J. -R. Casimir, J. -P. Briand, G. Guichard*. Synthesis of enantiopure 4-hydroxypipecolate and 4-hydroxylysine derivatives from a common 4,6dioxopiperidine carboxylate precursor. J. Org. Chem. 2004, 69, 130-141.

2003

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A. Poschalko, T. Rohr, H. Gruber, A. Bianco, G. Guichard, J. –P. Briand, V. Weber, D. Falkenhagen, SUBPOL: A Novel Sucrose-based Polymer Support for Solid-Phase Peptide Synthesis and Affinity Chromatography Applications. J. Am. Chem. Soc. 2003, 125, 13415-13426

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J./M. Lozano, G. Guichard, J. –P. Briand, J. L. Torres-Castellanos, F. Espejo, M. E. Patarroyo. Synthesis of ureidopeptides from succinimidyl carbamates obtained from N-terminus protected α-amino acids. Rev. Col. Quim. 2003, 32, 65-73.

2002 48

C. Hemmerlin, M. Marraud, D. Rognan, R. Graff, V. Semetey, J. –P. Briand, G. Guichard* Helix forming oligoureas: temperature-dependent NMR, structure determination and circular dichroism of a nonomer with functionalised side chain. Helv. Chim. Acta, 2002, 85, 3692-3711.

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J. Marin, C. Didierjean, A. Aubry, J.-P. Briand, G. Guichard*. Diastereoselective hydroxylation of 6-substituted piperidine-2-ones. An efficient synthesis of (2S,5R)-5-hydroxylysine and related aamino acids. J. Org. Chem. 2002, 67, 8440-8449.

46

J. R. Casimir*, G. Guichard, J.-P. Briand. Efficient synthesis of phtaloyl derivatives of α-amino carboxamides. Lett. Pept. Sci. 2002, 8, 89-93.

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J. R. Casimir*, G. Guichard, J.-P. Briand. Methyl-2-(succinimidyl-N-oxycarbonyl)benzoate (MSB). A New, Efficient Reagent for N-Phthaloylation of Amino Acid and Peptide Derivatives. J. Org. Chem. 2002, 67, 3764-3768.

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V. Semetey, C. Didierjean, J. –P. Briand, A. Aubry, G. Guichard*. Self-assembling organic nanotubes from enantiopure cyclo N,N’-linked-oligoureas: Design, synthesis and crystal structure. Angew. Chem. Int. Ed. 2002, 41, 1895-1898.

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V. Semetey, D. Rognan, C. Hemmerlin, R. Graff, J. –P. Briand, M. Marraud, G. Guichard*. Stable helical secondary structure in short chain N,N’-linked oligoureas bearing proteinogenic side chains. Angew. Chem. Int. Ed. 2002, 41, 1893-1895.

2001 42

B. Krust, R. Vienet, A. Cardona, C. Rougeot, E. Jacotot, C. Callebaut, G. Guichard, J.-P. Briand, J. M. Grognet, A. G. Hovanessian, L. Edelman. The anti-HIV pentameric pseudopeptide HB-19 is preferentially taken up in vivo by lymphoid organs where it forms a colmplex with nucleolin. Proc. Natl. Acad. Sci. USA 2001, 98, 14090-14095

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V. Semetey, C. Hemmerlin, C. Didierjean, A. P. Schaffner, A. Gimenez-Giner, A. Aubry, J. –P. Briand, M. Marraud, G. Guichard*. Unexpected stability of the urea cis-trans isomer in urea containing model pseudopeptides. Org. Lett. 2001, 3, 3843-3846.

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J. R. Casimir, G. Guichard, D. Tourwé, J.-P. Briand. Rapid procedure for N-phthaloylation of αamino carboxamides, α-aminoalcohols, α-amino esters and dipeptide derivatives. Synthesis 2001, 1985.

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A. Phan-Chan-Du, M.-C. Petit, G. Guichard, J.-P. Briand, S. Muller, M. T. Cung. Structure of antibody-bound peptides and retro-inverso analogues. A transferred nuclear overhauser effect spectroscopy and molecular dynamics approach. Biochemistry, 2001, 40, 5720-5727.

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J. Furrer, M. Piotto, M. Bourdeonneau, D. Limal, G. Guichard, K. Elbayed, J. Raya, J .P. Briand, A. Bianco. Evidence of secondary structure by high resolution magic angle spinning NMR spectroscopy of a bioactive peptide bound to different solid support. J. Am. Chem Soc.. 2001, 123, 4130-4138.

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C. Didierjean, A. Aubry, V. Semetey, J. -P. Briand, G. Guichard. The Crystal Structure of (S)-Osuccinimidyl-2-(tert-butoxycarbonylamino)-propylcarbamate Acta Cryst.2001 E57, o222-o224

36

J. R. Casimir*, G. Guichard and J. -P. Briand. Ultrasound and ZnCl2 promoted synthesis of phthaloyl derivatives of α-amino carboxamides Synthesis 2001, 75.

2000 35

A. Bianco, J. Furrer, D. Limal, G. Guichard, K. Elbayed, J. Raya, M. Piotto, J .P. Briand. Multistep synthesis of 2,5-diketopiperazines on different solid supports monitored by high resolution magic angle spinning NMR spectroscopy. J. Comb. Chem. 2000, 2, 681-690.

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G. Guichard,* A. Zerbib, F.-A. Le Gal, J. Hoebeke, F. Connan, J. –P. Briand, and J.-G. Guillet. Melanoma-peptide MART-1 (27-35) analogues with enhanced HLA-A2 binding capacity by introduction of a β-homo amino acid. Implications for recognition by tumor infiltrating lymphocytes. J. Med Chem 2000, 43, 3803-3808.

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J. R. Casimir, D. Tourwé, K. Iterbeke, G. Guichard and J. –P. Briand. Efficient Synthesis of (S)-4phthalimido-1,3,4,5-tetrahydro-8-(2,6-dichlorobenzyloxy)-3-oxo-2H-2-benzazepin-2-acetic acid (Pht-Hba(2,6-Cl2-Bn)-Gly-OH. J. Org. Chem. 2000, 65, 6487-6492.

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J. R. Casimir, C. Didierjean, A. Aubry, M. Rodriguez, J. –P. Briand and G. Guichard*. Stereoselective Alkylation of N-Boc-Protected-5-Substituted δ-Lactams: Synthesis of α,δ-Disubstituted δ−Amino Acids. Org. Lett. 2000, 2, 895-897.

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G. Guichard*, V. Semetey, M. Rodriguez, J. P. Briand, Solid phase synthesis of oligoureas using Osuccinimidyl-(9H-fluoren-9-ylmethoxycarbonylamino)-ethyl carbamate derivatives. Tetrahedron Lett. 2000, 41, 1553-1557.

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S. Nisole, B. Krust, E. Dam, A. Bianco, N. Seddiki, S. Loaec, C. Callebaut, G. Guichard, S. Muller, J. –P. Briand, A. G. Hovanessian. The HB-19 pseudopeptide 5[Kψ(CH2N)PR]-TASP inhibits attachment of T-lymphocyte- and macrophage-tropic HIV to permissive cells. AIDS Res. & Hum. Retroviruses, 2000, 16, 237-249.

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S. Calbo, G. Guichard, E. Mottez, P. Kourilsky, J. P. Briand, S. Muller, J. P. Abastado. Anti-tumor vaccination using a major histocompatibility complex (MHC) class I-restricted pseudopeptide with reduced peptide bond. J. Immunotherapy. 2000, 23, 125-130.

1999 28

G. Guichard*, V. Semetey, C. Didierjean, A. Aubry, J. P. Briand, M. Rodriguez. An effective preparation of O-succinimidyl-2-(tert-butoxycarbonylamino)-ethylcarbamate derivatives from β-amino-acids. Aplication to the synthesis of urea-containing pseudopeptides and oligoureas. J. Org. Chem. 1999, 64, 8702-8705.

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S. Nisole, B. Krust, C. Callebaut C, G. Guichard, S. Muller, J. P. Briand, A. G. Hovanessian. The antiHIV pseudopeptide HB-19 forms a complex with the cell-surface-expressed nucleolin independent of heparan sulfate proteoglycans. J Biol Chem 1999, 274, 27875-84

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S. Calbo, G. Guichard, P. Bousso, S. Muller, P. Kourilsky, J. P. Briand, J. P. Abastado, Role of peptide backbone in T cell recognition. J. Immunol. 1999, 162, 4657-4662

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N. Seddiki, S. Nisole, B. Krust, C. Callebaut, G. Guichard, S. Muller, J. –P. Briand, A. G. Hovanessian. The V3 loop-mimicking pseudopeptide 5[Kψ(CH2N)PR]-TASP inhibits HIV infection in primary macrophage cultures. AIDS Res Hum Retroviruses 1999 15, 381-90.

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24

M. C. Petit, N. Benkirane, G. Guichard, A. Phan Chan Du, M. Marraud, M. T. Cung, J. P. Briand, J. P., S. Muller. Solution structure of a retro-inverso peptide analogue mimicking the foot-andmouth disease virus major antigenic site : structural basis for its antigenic crossreactivity with the parent peptide. J. Biol. Chem. 1999, 274, 3686-3692

1998 23

S. Abele, G. Guichard, D. Seebach. (S)-β3-Homolysine and (S)-β3-Homoserine containing βpeptides. CD spectra in aqueous solution. Helv. Chim. Acta 1998,81, 2141-2156.

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D. Seebach, S. Abele, K. Gademann, G. Guichard, T. Hintermann, B. Jaun, J. Matthews, J. V. Schreiber. β2- and β3- peptides with proteinasceous side chains : synthesis and solution structures of constitutional isomers, a novel helical secondary structure and the influence of solvation and hydrophobic interactions on folding. Helv. Chim. Acta 1998, 81, 932-982.

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C. Callebaut, J. Blanco, N. Benkirane, B. Krust, E. Jacotot, G. Guichard,, N. Seddiki, J. Svab, E. Dam, S. Muller, J. –P. Briand, A. G. Hovanessian. Identification of V3 loop-binding proteins as potential receptors implicated in the binding of HIV particles to CD4+ cells. J. Biol. Chem. 1998, 273, 21988-21997.

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M. Ostankovitch, G. Guichard, F. Connan, S. Muller, A. Chaboissier, J. Hoebeke, J. Choppin, J.P. Briand, J. G. Guillet. A partially modified retro-inverso analogue modulates the cytokine profile of cytotoxic T-lymphocytes specific for an influenza virus epitope. J. Immunol. 1998, 161, 200-208.

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G. Guichard, S. Abele, D. Seebach. Preparation of N-Fmoc-protected β2- and β3- amino acids and their use as building blocks for the solid phase synthesis of β-peptides. Helv. Chim. Acta 1998, 81, 187-206.

1997 18

J. –P. Briand, N. Benkirane, G. Guichard, J. F. E. Newman, M. H. V. Van Regenmortel, F. Brown, S. Muller. A retro-inverso peptide correspondaing to the GH loop of foot-and-mouth disease virus elicits high levels of long-lasting protective neutralizing antibodies. Proc. Natl. Acad. Sci. USA 1997, 94, 12545-12550

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G. Guichard, D. Seebach, Solid-phase synthesis of β-oligopeptides. Chimia 1997, 51, 315-318

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K. Bartnes, K. Hannestad, G. Guichard, J. P. Briand. A retro-inverso analogue mimicks the cognate peptide epitope of a CD4+ T cell clone. Eur. J. Immunol. 1997, 27, 1387-1391.

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C. Callebaut, E. Jacotot, B. Krust, G. Guichard, J. Blanco, A. Valenzuela, J. Svab, S. Muller, J. P. Briand, A. G. Hovanessian. Pseudopeptide TASP inhibitors of HIV entry bind specifically to a 95 kDa cell surface protein. J. Biol. Chem. 1997, 272, 7159-7166.

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J. A. Carver, G. Esposito, P. Viglino, P. Fogolari, G. Guichard, J. –P. Briand, M. H. V. Van Regenmortel, F. Brown, P. Mascagni,. Structural comparison between retro-inverso and parent peptides. Molecular basis for the biological activity of a retro-inverso analogue of the immunodominant fragment of VP1 coat protein from foot and mouth disease virus. Biopolymers 1997, 41, 569-90.

1996 13

N. Benkirane, G. Guichard, J. P. Briand, S. Muller. Exploration of requirements for peptidomimetic immune recognition: antigenic and immunogenic properties of reduced peptide bond pseudopeptide analogues of a histone hexapeptide. J. Biol. Chem. 1996, 271, 33218-33224.

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12

G. Guichard*, F. Conan, R. Graff, M. Ostankovitch, S. Muller, J. G. Guillet, J. Choppin, J. –P. Briand. Partially modified retro-inverso pseudopeptides as non natural ligands for the human class I histocompatibility molecule, HLA-A2. J. Med. Chem. 1996, 39, 2030-2039.

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C. Callebaut, E. Jacotot, G. Guichard, B. Krust, M. A. Rey-Cuille, D. Cointe, N. Benkirane, J. Blanco, S. Muller, J. P. Briand, A. G. Hovanessian. Inhibition of HIV infection by pseudopeptides blocking viral envelope glycoprotein-mediated membrane fusion and cell death. Virology 1996, 218, 181192.

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G. Guichard, S. Muller, P. Mascagni, E. Giralt, M. H. V. Van Regenmortel, J. P. Briand. Structural limitations to antigenic mimicry achievable with retro-inverso peptides. Trends Biotechnol. 1996, 14, 44-45.

1992-1995 9

G. Guichard, S. Calbo, S. Muller, P. Kourilsky, J. -P. Briand, J. P. Abastado. Efficient binding of reduced peptide bond pseudopeptides to major histocompatibility complex class I molecule. J. Biol Chem. 1995, 270, 26057-26059.

8

J. P. Briand, G. Guichard, H. Dumortier, S. Muller. Retro-inverso peptidomimetics as new immunological probes: validation and application to the detection of antibodies in rheumatic diseases. J. Biol. Chem. 1995, 270, 20686-20691.

7

S. Muller, G. Guichard, N. Benkirane, F. Brown, M. H. V. Van Regenmortel, J. P. Briand. Enhanced immunogenicity and cross-reactivity of retro-inverso peptidomimetics of the major antigenic site of foot-and-mouth disease virus. Pept. Res. 1995, 8, 138-144.

6

N. Benkirane, G. Guichard, M. H. V. Van Regenmortel, J. P. Briand, S. Muller. Cross-reactivity of antibodies to retro-inverso peptidomimetics with the parent protein histone H3 and chromatin core particle: Specificity and kinetic rate-constant measurements. J. Biol. Chem. 1995, 270, 11921-11926.

5

G. Guichard, N. Benkirane, S. Muller, J. P. Briand. Synthesis and antigenic properties of reduced peptide bond pseudopeptide analogues of a histone H3 hexapeptide. Pept. Res. 1994, 7, 308-321.

4

G. Guichard, N. Benkirane, G. Zeder-Lutz, M. H. V. Van Regenmortel, J. P. Briand, S. Muller. Antigenic mimicry of natural L-peptides with retro-inverso-peptidomimetics. Proc. Natl. Acad. Sci. USA. 1994, 91, 9765-9769.

3

N. Benkirane, M. Friede, G. Guichard, J. P. Briand, M. H. V. Van Regenmortel, S. Muller. Antigenicity and immunogenicity of modified synthetic peptides containing D-amino acid residues: Antibodies to a D-enantiomer do recognize the parent L-hexapeptide and reciprocally. J. Biol. Chem. 1993, 268; 26279-26285.

2

G. Guichard, J. P. Briand, M. Friede. Synthesis of arginine aldehydes for the preparation of pseudopeptides. Pept. Res. 1993, 6, 121-124.

1

F. Poulat, G. Guichard, C. Gozé, F. Heitz, B. Calas, P. Berta. Synthesis of a large peptide mimicking the DNA properties of the sex determining protein SRY. FEBS Lett. 1992, 309, 385-388.

2.

OTHER PUBLICATIONS

8

Muller, S., Benkirane, N., Guichard, G., Van Regenmortel, M.H.V. The potential of retro-inverso peptides as synthetic vaccines. Exp. Opin. Invest. Drugs 1998, 7, 1429-1438.

7

Stemmer, C., Guichard, G.* Antigen-based T-cell-targeted immunotherapy : recent developments in autoimmunity and allergy. Exp. Opin. Ther. Patents 1998, 8, 819-830.

8

6

Van Regenmortel, M. H., Guichard, G., Benkirane, N., Briand, J. P., Muller, S., Brown, F. The potential of retro-inverso peptides as synthetic vaccines. Dev. Biol. Stand. 1998, 92, 139-43

5

Guichard, G.* MHC Ligands as potential therapeutics in the treatment of autoimmune and allergic diseases. Exp. Opin. Ther. Patents 1997, 7, 29-42.

4

Briand, J.P., Guichard, G., Guillet, J.G., Muller, S. Les pseudopeptides, des mimes efficaces. Biofutur, 1997, 168, 33-37.

3

Benkirane, N., Guichard, G., Briand, J.P., Muller, S., Brown, F. and Van Regenmortel, M.H.V. Mimicry of viral epitopes with retro-inverso peptides of increased stability. Dev Biol. Stand. 1996, 87, 283-291.

2

Briand, J.P., Guichard, G. and Muller, S. Interactions Pseudopeptides et Récepteurs du Système Immunitaire. Les Cahiers Imabio 1996, 17, 59-68.

1

Muller, S., Guichard, G. and Briand, J.P. Pseudopeptides in diagnosis and for use in the selective immunotherapy of autoimmune diseases. Actualités de Chimie Thérapeutique 1996, 22ème série, 29-36.

3.

BOOK CHAPTERS

4

P. Le Grel & G. Guichard, Foldamers based on remote intrastrand interactions In Foldamers; Huc I and Hecht S., Eds.; Wiley-VCH Verlag: Weinheim, 2007; pp 35-74.

3

G. Guichard*, Product Class 9: X2C=O; X=N,P. Ureas, P analogs: Polymers. In Science of Synthesis: Houben–Weyl Methods of Molecular Transformations, Vol. 18 Four Carbon–Heteroatom Bonds: X– C≡X, X=C=X, X2C=X, CX4; Knight, J. G., Ed.; Georg Thieme Verlag: Stuttgart, 2005; pp 759-820

2

G. Guichard*, β-Peptides, γ-Peptides and Isosteric Backbones : New Scaffolds with Controlled Shapes for mimicking protein secondary structure elements. In Pseudopeptide in Drug Development; Nielsen, P. E., Ed.; Wiley-VCH Verlag: Weinheim, 2004; pp33-120.

1

G. Guichard*, In Solid-Phase Synthesis : A Practical Guide; Kates, S. ; Albericio, F., Eds. Solid phase synthesis of pseudopeptides and oligomeric peptide backbone mimetics : Marcel Dekker :New York, 2000 , pp 649-703.

4.

PATENTS

16

G. Guichard, S. Fournel, J., Wieckoswki, Trouche N. Nouveaux Ligands de CD40, Leur Procédé de Préparation et leur utilisation pour la préparation de Médicaments - Brevet Français : 07/00809, déposant CNRS 15/02/2007

15

J. Courty, A. Hovanessian, J.P. Briand, G. Guichard, Y. Hamma. Pseudopeptide HB-19 et traitement du cancer. -FR #0603813, CNRS,

27/04/2006

14

G. Léna, P. Muller, E. Boilard, D. Rognan, G. Lambeau, G. Guichard* Compositions And Methods For The Inhibition of phospholipase A2 - Provisional US60/755,626 déposant ImmuPharma 18/01/2006

13

G. Léna, L. Rénia, E. Lallemand, G. Guichard* Compositions And Methods For The Treatment And Prevention Of Disease - Provisional US60/755,631 : déposant ImmuPharma 19/01/2006

9

12

G. Léna, L. Rénia, E. Lallemand, G. Guichard* Compositions And Methods For Synthesizing Novel Heterocyclic Therapeutics - Provisional US60/755,632 : déposant ImmuPharma 19/01/2006

11

A. Violette, R. Zimmer, J. P. Briand, G. Guichard* New hybrid oligomers, their preparation process and pharmaceutical compositions containing them - Provisional US : 0508-1130, déposant CNRS/BDS 18/03/2005

10

G. Guichard*, S. Fournel, J., Chaloin, O., Hoebeke, S. Wieckoswki, Trouche N. Nouveaux Ligands de CD40, Leur Procédé de Préparation et leur utilisation pour la préparation de Médicaments - Brevet Français : 04/13331, déposant CNRS 15/12/2004

9

G. Guichard*, S. Fournel, A. Bianco, J. Hoebeke, S. Muller Nouvelles molécules multimériques, leur procédé de préparation et leur utilisation pour la préparation de médicaments - Brevet Français : 02/06631, déposant CNRS 30/05/2002 - Demande de Brevet internationale : PCT/FR03/01613 28/05/2003 - Publication Internationale WO002003102207A3 08/04/2004 - Demande de valorisation #62781

8

G. Guichard*, V. Semetey, J. -P. Briand. Nouveaux oligomères d’urées, leur procédé de préparation et compositions pharmaceutiques les contenant. - Brevet français 01/12659, déposant CNRS 02/10/2001 - Demande internationale PCT/FR02/03355, déposant CNRS 02/10/2002 - Publication Internationale, WO 03/029198 10/04/2003 - Option sur licence: BioDelivery Systems, Mulhouse

7

S. Muller, F. Monneaux, J. -P. Briand, G. Guichard, J. G. Guillet. Utilisation de peptides comportant des modifications de type post-traductionnel dans le cadre du traitement de pathologies. - Brevet Français 01/12041, déposant CNRS 18/09/2001 - Demande internationale PCT/FR02/03186, déposant CNRS 18/09/2002 - Publication internationale WO 03/0250014 A2 27/03/2003 - Option sur licence: BioDelivery Systems, Mulhouse

6

G. Guichard*, V. Semetey, S. Plaué, M. Rodriguez, J. –P. Briand, Composés urée cycliques et leur procédé de fabrication - Brevet Français 00/07507 déposant CNRS/Neosystem - Demande internationale PCT FR01/01837 - Publication internationale WO 01/96318 A1

13/06/2000 13/06/2001 20/12/2001

5

G. Guichard*, V. Semetey, M. Rodriguez, J. –P. Briand. Nouveaux carbamates activés stables, leur procédé de préparation et leur utilisation pour la préparation d’urées. - Brevet Français 99/00330 déposant CNRS/Neosystem 14/01/1999 - Demande internationale PCT FR00/00080 14/01/2000 - Publication internationale WO002000042009A1 20/07/2000

4

J. G. Guillet, G. Guichard, M. Ostankovitch, F. Connan, A. Quesnel, J. Choppin, J. –P. Briand, S. Muller. Analogues peptidiques et leurs utilisations notamment dans des compositions pharmaceutiques et pour le diagnostic. - Brevet Français 97/05677 déposant CNRS/INSERM 07/05/1997 - Demande internationale PCT FR 98/00923 07/05/1998 - Publication internationale WO001998050423A2 12/11/1998

10

3

A. Hovanessian, C. Callebaut, B. Krust, E. Jacotot, S. Muller, J. P. Briand, G. Guichard Novel cell surface receptors for HIV retrovirus, therapeutic and diagnostic use. - Brevet US 4096997 déposant Institut Pasteur 12/03/1997 - Demande internationale PCT US98/01409 12/03/1998 - Publication internationale WO001998040480A1 17/09/1998

2

A. Hovanessian, C. Callebaut, B. Krust, E. Jacotot, S. Muller, J. P. Briand, G. Guichard Multiprésentation d'un analogue peptidique du substrat de la DPP IV, notamment de type KPR, afin d'inhiber l'entrée du HIV dans les cellules". - Brevet Français FR 94/04895 déposant Institut Pasteur 22/04/1994 - Demande internationale PCT FR95/00528 21/04/1995 - Publication internationale WO001995029190A1 02/11/1995

1

G. Guichard, S. Muller, J. P. Briand, M. H. V. Van Regenmortel Retropeptides, anticorps dirigés contre ces derniers et leurs utilisations pour la vaccination et le diagnostic in vitro. - Brevet Français 94/02950 déposant CNRS 14/03/1994 - Demande internationale PCT FR95/00292 13/03/1995 - Publication internationale WO001995024916A1 21/09/1995

5

SYMPOSIUM PROCEEDINGS

24

Guichard G, Trouche N, Wieckowski S, Sun W, Chaloin O, Bianco A, Hoebeke J, Schneider P, Fournel S. (2009) Rationally-designed multivalent architectures for mimicking homotrimers of CD40L, a member of the TNF superfamily. Adv Exp Med Biol. 611:355-7 (Proceedings of the 20th American Peptide Symposium, Montreal Canada, 2007).

23

Guichard G, Léna G, Boeglin J, Muller P, Boilard E, Lambeau G, Rognan D, Didierjean C. (2009) 1,3,5-Triazepan-2,6-diones as conformationally constrained dipeptide mimetics. In silico guided identification of sPLA2 inhibitors. Adv Exp Med Biol. 611:201-2. (Proceedings of the 20th American Peptide Symposium, Montreal Canada, 2007).

22

Fischer L, Lena G, Briand JP, Didierjean C, Guichard G. (2009) Mixing urea and amide bonds: synthesis and self-organization of new hybrid oligomers. Adv Exp Med Biol. 611:39-40. (Proceedings of the 20th American Peptide Symposium, Montreal Canada, 2007).

21

Claudon P et al. (2008) Fraternal twins! gamma-peptides and oligoureas are isosteric, isostructural foldamers endowed with yet distinct biomolecular recognition properties. J. Pep. Sci. 2008, 14, 177

20

Fischer L, Briand JP, Didierjean C, et al. (2008) Control of duplex formation and columnar selfassembly with Heterogeneous amide/urea macrocycles. J. Pep. Sci. 14, 186.

19

G. Guichard, Semetey, V., Rognan, D., Hemmerlin, C., Graff, R., Briand, J.P., Marraud, M. Enantiopure N,N’-linked oligoureas as foldamers. In Peptides 2002, Proceedings of the 27th European peptide symposium, 31 august-6 september 2002, Sorrento, Italie, pp954-955.

18

M. Marraud, Hemmerlin, C., Semetey, V., Didierjean, C., Aubry, A., G. Guichard. Experimental Structural Analysis Of Model Urea-Containing γ-Peptides Analogues. In Peptides 2002, Proceedings of the 27th European peptide symposium, 31 august-6 september 2002, Sorrento, Italie, pp806-807.

17

J. Marin, C. Didierjean, A. Aubry, J.P. Briand, G. Guichard. Disasereoselective Hydroxylation Of Piperidinones. An Experdient Synthesis Of (2S,5R)-5-Hydroxylysine. In Peptides 2002, Proceedings of the 27th European peptide symposium, 31 august-6 september 2002, Sorrento, Italie, pp126-127.

11

16

M. Marraud, C. Hemmerlin, C. Didierjean, A. Aubry,V. Semetey, A.-P. Schaffner, A. G. Giner, J. M. L., J.-P. Briand, G. Guichard, A short-range interaction of the cis-trans urea motif in ureapeptides. in 2nd international peptide symposium and 17th american peptide symposium, san diego (california), 2001, pp 348-349

15

V. Semetey, A.-P. Schaffner, J.-P. Briand, G. Guichard. Solution and Solid-Phase Synthesis Of Ureidopeptides And Oligourea/Peptide Hybrids. In Peptides 2000, Proceedings of the 26th European Peptide Symposium, Martinez and Fehrentz Eds, EDK, Paris, pp 263-264.

14

J. R. Casimir, C. Didierjean, A. Aubry, M. Rodriguez, J.-P. Briand, G. Guichard. Stereoselective Synthesis Of N-Boc-Protected-3,6-Disubstituted Piperidin-2-Ones and α,δ−Disubstituted δAmino Acids. In Peptides 2000, Proceedings of the 26th European Peptide Symposium, Martinez and Fehrentz Eds, EDK, Paris, pp 363-364.

13

A. Bianco, J. Furrer, D. Limal, G. Guichard, K. Elbayed, J. Raya, M. Piotto, J.-P. Briand. Hydroxyproline-Containing 2,5-Diketopiperazines: Synthesis On Different Solid Supports And Characterization By HR-MAS NMR. In Peptides 2000, Proceedings of the 26th European Peptide Symposium, Martinez and Fehrentz Eds, EDK, Paris, pp 953-954.

12

M. Marraud, A. Vicherat, C. Didierjean, A. Aubry, V. Semetey, A.-P. Schaffner, J.-P. Briand, G. Guichard Local Structures Induced By The Urea Fragment In Peptide Chains. In Peptides 2000, Proceedings of the 26th European Peptide Symposium, Martinez and Fehrentz Eds, EDK, Paris, pp 503-504.

11

V. Semetey, A.-P. Schaffner, M. Marraud, C. Didierjean, A. Aubry, M. Rodriguez, J.-P. Briand, G. Guichard. O-Succinimidyl Carbamate Derivatives From Amino Acids And Peptides : A General Entry To Urea-Based Peptidomimetics. In Peptides 2000, Proceedings of the 26th European Peptide Symposium, Martinez and Fehrentz Eds, EDK, Paris, pp 161-162.

10

D. Limal, C. Stemmer, J. Hoebeke, G. Guichard, R. Casimir, C. Didierjean, A. Aubry, S. Muller, H.P. Pircher, J.-P. Briand. A carbaza paptide acts as a super agonist of cytotoxic T cell response. In Peptides 2000, Proceedings of the 26th European Peptide Symposium, Martinez and Fehrentz Eds, EDK, Paris, pp 885-886.

9

S. Calbo, P. Bousso, G. Guichard, J. P. Abastado, The mouse T cell response against the HLA-CW3 peptide and a related pseudopeptide. In 10th International Congress of IMMUNOLOGY : 1-6 November 1998, New Dehli, India. Monduzzi Editore SpA, Bologna, 1998, pp267-272.

8

G. Guichard, M. Ostankovitch, F. Connan, J. Choppin, J. Neimark, J. Hoebeke, S. Muller, J. G. Guillet, J. P. Briand. Modulation of the cytokine profile of CD8+ T cells specific for an influenza virus epitope by a partially Modified retro-inverso pseudpeptide. In Peptides. 1998. Proceedings of the twenty-fifth European Peptide Symposium August 30-September 4 1998, Budapest, Hungary, Bajusz, S., Hudecz, F., Eds ; Akadémiai Kiado : Budapest, 1999, pp584-585.

7

G. Esposito, J. A. Carver, P. Viglino, F. Fogliani, G. Guichard, M. H. V. Van Regenmortel, J. P. Briand, P. Mascagni. Structural analogy between retro-inverso and parent peptide sequences. Molecular basis for the biological activity of a retro-inverso analogue of the immunodominant fragment of foot and mouth disease virus. In Peptides. 1996. Proceedings of the twenty-fourth European Peptide Symposium September 8-13 1996, Edinburgh, Scotland, Ramage, R., Epton, R., Eds ; Mayflower Scientific Ltd :Kingswinford, 1998, pp.369-370

6

G. Guichard, F. Conan , R. Graff, M. Ostankovitch, S. Muller, J; G. Guillet J. Choppin, J. P. Briand. Partially modified retro-inverso pseudopeptides as non natural ligands for the human class I histocompatibility molecule, HLA-A2. In Peptides. 1996. Proceedings of the twenty-fourth European Peptide Symposium September 8-13 1996, Edinburgh, Scotland, Ramage, R., Epton, R., Eds ; Mayflower Scientific Ltd :Kingswinford, 1998, pp.449-450.

12

5

G. Guichard, N. Benkirane, J. P. Briand, S. Muller S. Exploration of requirements for peptidomimetic immune recognition: antigenic and immunogenic properties of reduced peptide bond pseudopeptide analogues of a histone hexapeptide. In Peptides. 1996. Proceedings of the twenty-fourth European Peptide Symposium September 8-13 1996, Edinburgh, Scotland, Ramage, R., Epton, R., Eds ; Mayflower Scientific Ltd :Kingswinford, 1998, pp.445-446.

4

G. Guichard, N. Benkirane, J. P. Briand, J. F. E. Newman, M. H. V. Van Regenmortel, F. Brown, S. Muller. Mimicry of an immunodominant epitope of foot-and-mouth disease virus with retroinverso isomers. A new approach in the design of peptide-based vaccine. In Peptides. 1996. Proceedings of the twenty-fourth European Peptide Symposium September 8-13 1996, Edinburgh, Scotland, Ramage, R., Epton, R., Eds ; Mayflower Scientific Ltd :Kingswinford, 1998, pp.447-448.

3

G. Guichard. Use of retro-inverso pseudopeptides for mimicking antigenic sites and as potential synthetic vaccines. In Peptides. Chemistry, Structure and biology. Proceedings of the Fourteenth American Peptide Symposium June 18-23, 1995, Columbus, Ohio, USA, Kaumaya, P.T.P., Hodges, R.S., Eds; ESCOM: Leiden, 1996, pp827-828.

2

N. Benkirane, G. Guichard,, M. H. V. Van Regenmortel, J. P. Briand, S. Muller. Cross-reactivity of antibodies to retro-inverso peptidomimetics with the parent protein histone H3 and chromatin core particle: Specificity and kinetic rate-constant measurements. In Peptides. Chemistry, Structure and biology. Proceedings of the Fourteenth American Peptide Symposium June 18-23, 1995, Columbus, Ohio, USA, Kaumaya, P.T.P., Hodges, R.S., Eds; ESCOM: Leiden, 1996, pp798-799.

1

G. Guichard, N. Benkirane, J. Neimark, M. H. V. Van Regenmortel, J. P. Briand, S. Muller, Antigenic mimicry of natural L-peptides with retro-inverso-peptidomimetics. In Peptides. 1994. Proceedings of the twenty-third European Peptide Symposium September 4-10, 1994, Braga, Portugal, Maia, H.L.S., Eds; ESCOM: Leiden, 1995, pp849-850.

13