List of works - Gilles Guichard

1,3,5-Triazepan-2,6-diones as conformationally constrained dipeptide mimetics. In silico guided identification of sPLA2 inhibitors.

scientific article published in January 2009

1,3,5-Triazepane-2,6-diones as structurally diverse and conformationally constrained dipeptide mimetics: identification of malaria liver stage inhibitors from a small pilot library

scientific article

5-(3,4-Dimethoxybenzyl)-7-isopropyl-1,3,5-triazepane-2,6-dione acetonitrile solvate refined using a multipolar atom model.

scientific article published on 12 May 2010

A cell-penetrating foldamer with a bioreducible linkage for intracellular delivery of DNA.

scientific article published on 5 August 2015

A post-elongation strategy for the introduction of guanidinium units in the main chain of helical oligourea foldamers.

scientific article

A retro-inverso analog mimics the cognate peptide epitope of a CD4+ T cell clone

scientific article published on 01 June 1997

A retro-inverso peptide corresponding to the GH loop of foot-and-mouth disease virus elicits high levels of long-lasting protective neutralizing antibodies.

scientific article published on November 1997

Anatomy of an Oligourea Six-Helix Bundle

scientific article published on 15 August 2016

Anion Recognition by Aliphatic Helical Oligoureas

scientific article

Anion-macrodipole interactions: self-assembling oligourea/amide macrocycles as anion transporters that respond to membrane polarization

scientific article published in November 2009

Antibacterial activity of a dual peptide targeting the <i>Escherichia coli</i> sliding clamp and the ribosome

scientific article published in 2020

Antitumor vaccination using a major histocompatibility complex (MHC) class I-restricted pseudopeptide with reduced peptide bond

scientific article published on 01 January 2000

Aza-beta3-cyclopeptides: a new way of controlling nitrogen chirality

scientific article published in October 2009

Calculations on the electronic excited states of ureas and oligoureas

scientific article published on 03 March 2007

Condensation approach to aliphatic oligourea foldamers: helices with N-(pyrrolidin-2-ylmethyl)ureido junctions

scientific article published on 04 October 2011

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.

scientific article published in January 2010

Control of duplex formation and columnar self-assembly with heterogeneous amide/urea macrocycles

scientific article published in January 2009

Controlling Helix Formation in the γ-Peptide Superfamily: Heterogeneous Foldamers with Urea/Amide and Urea/Carbamate Backbones

scientific article published on 4 March 2013

Cooperativity in the interaction of synthetic CD40L mimetics with CD40 and its implication in cell signaling.

scientific article published on 24 February 2007

Cross-reactivity of antibodies to retro-inverso peptidomimetics with the parent protein histone H3 and chromatin core particle. Specificity and kinetic rate-constant measurements

scientific article published on 01 May 1995

DEUSS: a perdeuterated poly(oxyethylene)-based resin for improving HRMAS NMR studies of solid-supported molecules

scientific article published in September 2004

Design and Structure Determination of a Composite Zinc Finger Containing a Nonpeptide Foldamer Helical Domain

scientific article published on 04 February 2019

Diastereoselective hydroxylation of 6-substituted piperidin-2-ones. An efficient synthesis of (2S,5R)-5-hydroxylysine and related alpha-amino acids

scientific article

Differential modes of peptide binding onto replicative sliding clamps from various bacterial origins

scientific article

Direct functionalisation of group 10 N-heterocyclic carbene complexes for diversity enhancement

scientific article published on 18 April 2011

Effect of replacing main-chain ureas with thiourea and guanidinium surrogates on the bactericidal activity of membrane active oligourea foldamers

scientific article published on 29 April 2017

Efficient binding of reduced peptide bond pseudopeptides to major histocompatibility complex class I molecule

scientific article published on 01 November 1995

Experimental and theoretical study of the vibrational spectra of oligoureas: helical versus β-sheet-type secondary structures

scientific article published on 29 March 2011

Exploration of requirements for peptidomimetic immune recognition. Antigenic and immunogenic properties of reduced peptide bond pseudopeptide analogues of a histone hexapeptide.

scientific article

Exploring helical folding of oligoureas during chain elongation by high-resolution magic-angle-spinning (HRMAS) NMR spectroscopy.

scientific article published in January 2008

Exploring nitrogen ligand diversity in trans-N-heterocyclic carbene-amine platinum complexes: synthesis, characterization, and application to fluorescence

scientific article published on 4 April 2013

Foldamers in Medicinal Chemistry

scientific article published on 14 February 2017

Formation and Modulation of Nanotubular Assemblies of Oligourea Foldamers in Aqueous Conditions using Alcohol Additives

scientific article published on 30 June 2020

Genes of the N-methylglutamate pathway are essential for growth of Methylobacterium extorquens DM4 with monomethylamine

scientific article published on 28 March 2014

Helical Oligourea Foldamers as Powerful Hydrogen Bonding Catalysts for Enantioselective C-C Bond-Forming Reactions

scientific article

Helix-forming propensity of aliphatic urea oligomers incorporating noncanonical residue substitution patterns.

scientific article published on 13 March 2013

Hetero-oligomerization between the TNF receptor superfamily members CD40, Fas and TRAILR2 modulate CD40 signalling

scientific article published on 09 February 2017

Hybrid Cell-Penetrating Foldamer with Superior Intracellular Delivery Properties and Serum Stability

scientific article published on 01 April 2019

Identification of V3 loop-binding proteins as potential receptors implicated in the binding of HIV particles to CD4(+) cells.

scientific article

In silico-guided target identification of a scaffold-focused library: 1,3,5-triazepan-2,6-diones as novel phospholipase A2 inhibitors

scientific article

In situ iodination and X-ray crystal structure of a foldamer helix bundle

scientific article published on 01 January 2016

Inducing achiral aliphatic oligoureas to fold into helical conformations

article

Influence of achiral units with gem-dimethyl substituents on the helical character of aliphatic oligourea foldamers

scientific article published in August 2013

Insight into Substrate Recognition by Urea-Based Helical Foldamer Catalysts Using a DFT Global Optimization Approach

scientific article published in 2022

Interaction of a Model Peptide on Gram Negative and Gram Positive Bacterial Sliding Clamps

scientific article published on 05 April 2019

Isosteric substitutions of urea to thiourea and selenourea in aliphatic oligourea foldamers: site-specific perturbation of the helix geometry

scientific article published on 21 December 2014

Ligand dimerization programmed by hybridization to study multimeric ligand-receptor interactions.

scientific article

Melanoma peptide MART-1(27-35) analogues with enhanced binding capacity to the human class I histocompatibility molecule HLA-A2 by introduction of a beta-amino acid residue: implications for recognition by tumor-infiltrating lymphocytes.

scientific article

Methyl 2-((succinimidooxy)carbonyl)benzoate (MSB): a new, efficient reagent for N-phthaloylation of amino acid and peptide derivatives

scientific article published in May 2002

Mimicking helical antibacterial peptides with nonpeptidic folding oligomers.

scientific article

Molecular Recognition within the Cavity of a Foldamer Helix Bundle: Encapsulation of Primary Alcohols in Aqueous Conditions

scientific article

Multimerization of an apoptogenic TRAIL-mimicking peptide by using adamantane-based dendrons.

scientific article published on 13 December 2012

Multivalent DR5 peptides activate the TRAIL death pathway and exert tumoricidal activity

scientific article

N,N'-linked oligoureas as foldamers: chain length requirements for helix formation in protic solvent investigated by circular dichroism, NMR spectroscopy, and molecular dynamics

scientific article published in February 2005

N-Heterocyclic Carbene-Polyethylenimine Platinum Complexes with Potent in Vitro and in Vivo Antitumor Efficacy

scientific article published on 26 July 2016

N-glycosylation of mouse TRAIL-R and human TRAIL-R1 enhances TRAIL-induced death

scientific article published on 10 February 2017

Native ESI Mass Spectrometry Can Help to Avoid Wrong Interpretations from Isothermal Titration Calorimetry in Difficult Situations.

scientific article published on 12 December 2016

Partially modified retro-inverso pseudopeptides as non-natural ligands for the human class I histocompatibility molecule HLA-A2

scientific article published on 01 May 1996

Peptide-oligourea hybrids analogue of GLP-1 with improved action in vivo

scientific article published on 25 February 2019

Porous 3-D honeycomb architecture by self-assembly of helical H-bonded molecular tapes

scientific article published on 11 September 2006

Proline-rich antimicrobial peptides targeting protein synthesis.

scientific article

Propensity for local folding induced by the urea fragment in short-chain oligomers

scientific article published on 15 May 2008

Proteolytically Stable Foldamer Mimics of Host-Defense Peptides with Protective Activities in a Murine Model of Bacterial Infection

scientific article published on 16 August 2016

Pseudopeptide TASP inhibitors of HIV entry bind specifically to a 95-kDa cell surface protein.

scientific article published on March 1997

Rationally-designed multivalent architectures for mimicking homotrimers of CD40L, a member of the TNF superfamily

scientific article published in January 2009

Relationship between the agonist activity of synthetic ligands of TRAIL-R2 and their cell surface binding modes.

scientific article published on 17 February 2018

SUBPOL: a novel SUcrose-Based Polymer support for solid-phase peptide synthesis and affinity chromatography applications.

scientific article

Self-assembling organic nanotubes from enantiopure cyclo-N,N'-linked oligoureas: design, synthesis, and crystal structure.

scientific article published in June 2002

Sequencing of oligourea foldamers by tandem mass spectrometry.

scientific article

Shaping quaternary assemblies of water-soluble non-peptide helical foldamers by sequence manipulation

scientific article published on 28 September 2015

Small multivalent architectures mimicking homotrimers of the TNF superfamily member CD40L: delineating the relationship between structure and effector function

scientific article

Solid state NMR studies of oligourea foldamers: interaction of 15N-labelled amphiphilic helices with oriented lipid membranes

scientific article published on 04 January 2012

Solid-phase synthesis of CD40L mimetics.

scientific article published on 10 March 2006

Solution structure determination of oligoureas using methylene spin state selective NMR at 13C natural abundance.

scientific article

Solution structure of a retro-inverso peptide analogue mimicking the foot-and-mouth disease virus major antigenic site. Structural basis for its antigenic cross-reactivity with the parent peptide

scientific article

Stabilized helical peptides: overview of the technologies and therapeutic promises.

scientific article published on 22 July 2011

Structural characterization of short hybrid urea/carbamate (U/C) foldamers: A case of partial helix unwinding.

scientific article published in November 2013

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

scientific article published in April 1997

Structural limitations to antigenic mimicry achievable with retroinverso (all-D-retro) peptides

scientific article published on 01 February 1996

Structure of antibody-bound peptides and retro-inverso analogues. A transferred nuclear Overhauser effect spectroscopy and molecular dynamics approach

scientific article

Structure-based design of short peptide ligands binding onto the E. coli processivity ring

scientific article

Surfactant-facilitated crystallisation of water-soluble foldamers

scientific article published on 10 February 2016

Synthesis and folding propensity of aliphatic oligoureas containing repeats of proline-type units

scientific article published on 27 May 2014

Synthesis of a large peptide mimicking the DNA binding properties of the sex determining protein, SRY

scientific article published on 01 September 1992

Synthesis of enantiopure 4-hydroxypipecolate and 4-hydroxylysine derivatives from a common 4,6-dioxopiperidinecarboxylate precursor

scientific article

Synthesis of glycopeptides from type II collagen-incorporating galactosylated hydroxylysine mimetics and their use in studying the fine specificity of arthritogenic T cells

scientific article published in October 2005

Synthetic foldamers.

scientific article published on 11 April 2011

Synthetic ligands of death receptor 5 display a cell-selective agonistic effect at different oligomerization levels.

scientific article published on 9 July 2016

TRAIL receptor gene editing unveils TRAIL-R1 as a master player of apoptosis induced by TRAIL and ER stress

scientific article published on 27 December 2016

The HB-19 pseudopeptide 5[Kpsi(CH2N)PR]-TASP inhibits attachment of T lymophocyte- and macrophage-tropic HIV to permissive cells

scientific article

The V3 Loop-Mimicking Pseudopeptide 5[K psi(CH2N)PR]- TASP Inhibits HIV Infection in Primary Macrophage Cultures

article

The anti-HIV pseudopeptide HB-19 forms a complex with the cell-surface-expressed nucleolin independent of heparan sulfate proteoglycans

scientific article

The meso Helix: Symmetry and Symmetry-Breaking in Dynamic Oligourea Foldamers with Reversible Hydrogen-Bond Polarity

scientific article published on 14 June 2016

The meso Helix: Symmetry and Symmetry-Breaking in Dynamic Oligourea Foldamers with Reversible Hydrogen-Bond Polarity

The potential of retro-inverso peptides as synthetic vaccines.

scientific article published in September 1998

The proline-rich antimicrobial peptide Onc112 inhibits translation by blocking and destabilizing the initiation complex

scientific article

Thioether analogues of disulfide-bridged cyclic peptides targeting death receptor 5: conformational analysis, dimerisation and consequences for receptor activation

scientific article published on 8 December 2014

Unexpected stability of the urea cis-trans isomer in urea-containing model pseudopeptides

scientific article published on 01 November 2001

Ureidopeptide GLP-1 analogues with prolonged activity in vivo via signal bias and altered receptor trafficking

scientific article published on 11 September 2019

tert-Butyl (6S)-4-hydroxy-6-isobutyl-2-oxo-1,2,5,6-tetrahydropyridine-1-carboxylate and tert-butyl (4R,6S)-4-hydroxy-6-isobutyl-2-oxopiperidine-1-carboxylate

scientific article published on 10 February 2004

tert-Butyl 3-oxo-2-oxa-5-aza-bicyclo-[2.2.1]heptane-5-carboxyl-ate

scientific article published on 30 September 2008

α-Peptide-Oligourea Chimeras: Stabilization of Short α-Helices by Non-Peptide Helical Foldamers

scientific article published on 01 July 2015

List of works by Gilles Guichard

1,3,5-Triazepan-2,6-diones as conformationally constrained dipeptide mimetics. In silico guided identification of sPLA2 inhibitors.

1,3,5-Triazepane-2,6-diones as structurally diverse and conformationally constrained dipeptide mimetics: identification of malaria liver stage inhibitors from a small pilot library

5-(3,4-Dimethoxybenzyl)-7-isopropyl-1,3,5-triazepane-2,6-dione acetonitrile solvate refined using a multipolar atom model.

A cell-penetrating foldamer with a bioreducible linkage for intracellular delivery of DNA.

A post-elongation strategy for the introduction of guanidinium units in the main chain of helical oligourea foldamers.

A retro-inverso analog mimics the cognate peptide epitope of a CD4+ T cell clone

A retro-inverso peptide corresponding to the GH loop of foot-and-mouth disease virus elicits high levels of long-lasting protective neutralizing antibodies.

Anatomy of an Oligourea Six-Helix Bundle

Anion Recognition by Aliphatic Helical Oligoureas

Anion-macrodipole interactions: self-assembling oligourea/amide macrocycles as anion transporters that respond to membrane polarization

Antibacterial activity of a dual peptide targeting the <i>Escherichia coli</i> sliding clamp and the ribosome

Antitumor vaccination using a major histocompatibility complex (MHC) class I-restricted pseudopeptide with reduced peptide bond

Aza-beta3-cyclopeptides: a new way of controlling nitrogen chirality

Calculations on the electronic excited states of ureas and oligoureas

Condensation approach to aliphatic oligourea foldamers: helices with N-(pyrrolidin-2-ylmethyl)ureido junctions

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.

Control of duplex formation and columnar self-assembly with heterogeneous amide/urea macrocycles

Controlling Helix Formation in the γ-Peptide Superfamily: Heterogeneous Foldamers with Urea/Amide and Urea/Carbamate Backbones

Cooperativity in the interaction of synthetic CD40L mimetics with CD40 and its implication in cell signaling.

Cross-reactivity of antibodies to retro-inverso peptidomimetics with the parent protein histone H3 and chromatin core particle. Specificity and kinetic rate-constant measurements

DEUSS: a perdeuterated poly(oxyethylene)-based resin for improving HRMAS NMR studies of solid-supported molecules

Design and Structure Determination of a Composite Zinc Finger Containing a Nonpeptide Foldamer Helical Domain

Diastereoselective hydroxylation of 6-substituted piperidin-2-ones. An efficient synthesis of (2S,5R)-5-hydroxylysine and related alpha-amino acids

Differential modes of peptide binding onto replicative sliding clamps from various bacterial origins

Direct functionalisation of group 10 N-heterocyclic carbene complexes for diversity enhancement

Effect of replacing main-chain ureas with thiourea and guanidinium surrogates on the bactericidal activity of membrane active oligourea foldamers

Efficient binding of reduced peptide bond pseudopeptides to major histocompatibility complex class I molecule

Experimental and theoretical study of the vibrational spectra of oligoureas: helical versus β-sheet-type secondary structures

Exploration of requirements for peptidomimetic immune recognition. Antigenic and immunogenic properties of reduced peptide bond pseudopeptide analogues of a histone hexapeptide.

Exploring helical folding of oligoureas during chain elongation by high-resolution magic-angle-spinning (HRMAS) NMR spectroscopy.

Exploring nitrogen ligand diversity in trans-N-heterocyclic carbene-amine platinum complexes: synthesis, characterization, and application to fluorescence

Foldamers in Medicinal Chemistry

Formation and Modulation of Nanotubular Assemblies of Oligourea Foldamers in Aqueous Conditions using Alcohol Additives

Genes of the N-methylglutamate pathway are essential for growth of Methylobacterium extorquens DM4 with monomethylamine

Helical Oligourea Foldamers as Powerful Hydrogen Bonding Catalysts for Enantioselective C-C Bond-Forming Reactions

Helix-forming propensity of aliphatic urea oligomers incorporating noncanonical residue substitution patterns.

Hetero-oligomerization between the TNF receptor superfamily members CD40, Fas and TRAILR2 modulate CD40 signalling

Hybrid Cell-Penetrating Foldamer with Superior Intracellular Delivery Properties and Serum Stability

Identification of V3 loop-binding proteins as potential receptors implicated in the binding of HIV particles to CD4(+) cells.

In silico-guided target identification of a scaffold-focused library: 1,3,5-triazepan-2,6-diones as novel phospholipase A2 inhibitors

In situ iodination and X-ray crystal structure of a foldamer helix bundle

Inducing achiral aliphatic oligoureas to fold into helical conformations

Influence of achiral units with gem-dimethyl substituents on the helical character of aliphatic oligourea foldamers

Insight into Substrate Recognition by Urea-Based Helical Foldamer Catalysts Using a DFT Global Optimization Approach

Interaction of a Model Peptide on Gram Negative and Gram Positive Bacterial Sliding Clamps

Isosteric substitutions of urea to thiourea and selenourea in aliphatic oligourea foldamers: site-specific perturbation of the helix geometry

Ligand dimerization programmed by hybridization to study multimeric ligand-receptor interactions.

Melanoma peptide MART-1(27-35) analogues with enhanced binding capacity to the human class I histocompatibility molecule HLA-A2 by introduction of a beta-amino acid residue: implications for recognition by tumor-infiltrating lymphocytes.

Methyl 2-((succinimidooxy)carbonyl)benzoate (MSB): a new, efficient reagent for N-phthaloylation of amino acid and peptide derivatives

Mimicking helical antibacterial peptides with nonpeptidic folding oligomers.

Molecular Recognition within the Cavity of a Foldamer Helix Bundle: Encapsulation of Primary Alcohols in Aqueous Conditions

Multimerization of an apoptogenic TRAIL-mimicking peptide by using adamantane-based dendrons.

Multivalent DR5 peptides activate the TRAIL death pathway and exert tumoricidal activity

N,N'-linked oligoureas as foldamers: chain length requirements for helix formation in protic solvent investigated by circular dichroism, NMR spectroscopy, and molecular dynamics

N-Heterocyclic Carbene-Polyethylenimine Platinum Complexes with Potent in Vitro and in Vivo Antitumor Efficacy

N-glycosylation of mouse TRAIL-R and human TRAIL-R1 enhances TRAIL-induced death

Native ESI Mass Spectrometry Can Help to Avoid Wrong Interpretations from Isothermal Titration Calorimetry in Difficult Situations.

Partially modified retro-inverso pseudopeptides as non-natural ligands for the human class I histocompatibility molecule HLA-A2

Peptide-oligourea hybrids analogue of GLP-1 with improved action in vivo

Porous 3-D honeycomb architecture by self-assembly of helical H-bonded molecular tapes

Proline-rich antimicrobial peptides targeting protein synthesis.

Propensity for local folding induced by the urea fragment in short-chain oligomers

Proteolytically Stable Foldamer Mimics of Host-Defense Peptides with Protective Activities in a Murine Model of Bacterial Infection

Pseudopeptide TASP inhibitors of HIV entry bind specifically to a 95-kDa cell surface protein.

Rationally-designed multivalent architectures for mimicking homotrimers of CD40L, a member of the TNF superfamily

Relationship between the agonist activity of synthetic ligands of TRAIL-R2 and their cell surface binding modes.

SUBPOL: a novel SUcrose-Based Polymer support for solid-phase peptide synthesis and affinity chromatography applications.

Self-assembling organic nanotubes from enantiopure cyclo-N,N'-linked oligoureas: design, synthesis, and crystal structure.

Sequencing of oligourea foldamers by tandem mass spectrometry.

Shaping quaternary assemblies of water-soluble non-peptide helical foldamers by sequence manipulation

Small multivalent architectures mimicking homotrimers of the TNF superfamily member CD40L: delineating the relationship between structure and effector function

Solid state NMR studies of oligourea foldamers: interaction of 15N-labelled amphiphilic helices with oriented lipid membranes

Solid-phase synthesis of CD40L mimetics.

Solution structure determination of oligoureas using methylene spin state selective NMR at 13C natural abundance.

Solution structure of a retro-inverso peptide analogue mimicking the foot-and-mouth disease virus major antigenic site. Structural basis for its antigenic cross-reactivity with the parent peptide

Stabilized helical peptides: overview of the technologies and therapeutic promises.

Structural characterization of short hybrid urea/carbamate (U/C) foldamers: A case of partial helix unwinding.

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

Structural limitations to antigenic mimicry achievable with retroinverso (all-D-retro) peptides