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  1. Article ; Online: Cage-like structures based on constrained cyclic arylopeptoids.

    Akhdar, Ayman / Nauton, Lionel / Jouffret, Laurent / Faure, Sophie / Gautier, Arnaud

    Chemical communications (Cambridge, England)

    2023  Volume 59, Issue 52, Page(s) 8087–8090

    Abstract: The access to cupola-like or tube-like structures ... ...

    Abstract The access to cupola-like or tube-like structures from
    Language English
    Publishing date 2023-06-27
    Publishing country England
    Document type Journal Article
    ZDB-ID 1472881-3
    ISSN 1364-548X ; 1359-7345 ; 0009-241X
    ISSN (online) 1364-548X
    ISSN 1359-7345 ; 0009-241X
    DOI 10.1039/d3cc01956j
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  2. Article ; Online: Arylopeptoid oligomers functionalised by combinatorial or sequential on-resin click chemistry using a copper(I)-N-heterocyclic carbene catalyst.

    Akhdar, Ayman / Faure, Sophie / Gautier, Arnaud

    Organic & biomolecular chemistry

    2022  Volume 20, Issue 12, Page(s) 2402–2406

    Abstract: An efficient on-resin click chemistry protocol using a stable copper(I)-N-heterocyclic carbene catalyst is developed for post-functionalization ... ...

    Abstract An efficient on-resin click chemistry protocol using a stable copper(I)-N-heterocyclic carbene catalyst is developed for post-functionalization of
    MeSH term(s) Catalysis ; Click Chemistry ; Copper ; Methane/analogs & derivatives
    Chemical Substances carbene (2465-56-7) ; Copper (789U1901C5) ; Methane (OP0UW79H66)
    Language English
    Publishing date 2022-03-23
    Publishing country England
    Document type Journal Article
    ZDB-ID 2097583-1
    ISSN 1477-0539 ; 1477-0520
    ISSN (online) 1477-0539
    ISSN 1477-0520
    DOI 10.1039/d2ob00163b
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  3. Article ; Online: N-Alkylated Aromatic Poly- and Oligoamides.

    Akhdar, Ayman / Gautier, Arnaud / Hjelmgaard, Thomas / Faure, Sophie

    ChemPlusChem

    2021  Volume 86, Issue 2, Page(s) 298–312

    Abstract: N-alkylated aromatic poly- and oligoamides are a particular class of abiotic foldamers that is deprived of the capability of forming intramolecular hydrogen-bonding networks to stabilize their tri-dimensional structure. The alkylation of the backbone ... ...

    Abstract N-alkylated aromatic poly- and oligoamides are a particular class of abiotic foldamers that is deprived of the capability of forming intramolecular hydrogen-bonding networks to stabilize their tri-dimensional structure. The alkylation of the backbone amide nitrogen atoms greatly increases the chemical diversity accessible for aromatic poly- and oligoamides. However, the nature and the conformational preferences of the N,N-disubstituted amides profoundly modify the folding properties of these aromatic poly- and oligoamides. In this Review, representative members of this class of aromatic poly- and oligoamides will be highlighted, among them N-alkylated phenylene terephthalamides, benzanilides, pyridylamides, and aminomethyl benzamide oligomers. The principal synthetic pathways to the main classes of N-alkylated aromatic polyamides with narrow to broad molecular-weight distribution, or oligoamides with specific sequences, will be detailed and their foldameric properties will be discussed. The Review will end by describing the few applications reported to date and future prospects for the field.
    Language English
    Publishing date 2021-03-15
    Publishing country Germany
    Document type Journal Article ; Review ; Research Support, Non-U.S. Gov't
    ISSN 2192-6506
    ISSN (online) 2192-6506
    DOI 10.1002/cplu.202000825
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  4. Article ; Online: Design of Triazolium-Grafted Peptidomimetic Macrocycles with Facial Amphipathicity to Target Pathogenic Bacteria.

    Guerinot, Cassandra / Malige, Mélodie / Charbonnel, Nicolas / Malosse, Killian / Jouffret, Laurent / Taillefumier, Claude / Roy, Olivier / Forestier, Christiane / Faure, Sophie

    Organic letters

    2024  Volume 26, Issue 19, Page(s) 4088–4092

    Abstract: Access to 1,2,3-triazolium-grafted peptoid macrocycles was developed by macrocyclization and multivalent postmodification of linear peptoid oligomers carrying an alternance of benzylic and propargyl groups as side chains. X-ray analysis and NMR studies ... ...

    Abstract Access to 1,2,3-triazolium-grafted peptoid macrocycles was developed by macrocyclization and multivalent postmodification of linear peptoid oligomers carrying an alternance of benzylic and propargyl groups as side chains. X-ray analysis and NMR studies revealed a conformational preference for constrained hairpin-shaped structures leading to the facial amphipathic character of these macrocycles. A preliminary evaluation showed the antimicrobial activities of these new cationic amphipathic architectures.
    MeSH term(s) Triazoles/chemistry ; Triazoles/pharmacology ; Molecular Structure ; Peptidomimetics/chemistry ; Peptidomimetics/pharmacology ; Peptidomimetics/chemical synthesis ; Anti-Bacterial Agents/pharmacology ; Anti-Bacterial Agents/chemistry ; Anti-Bacterial Agents/chemical synthesis ; Microbial Sensitivity Tests ; Macrocyclic Compounds/chemistry ; Macrocyclic Compounds/pharmacology ; Macrocyclic Compounds/chemical synthesis ; Peptoids/chemistry ; Peptoids/pharmacology ; Peptoids/chemical synthesis ; Crystallography, X-Ray ; Bacteria/drug effects
    Language English
    Publishing date 2024-05-06
    Publishing country United States
    Document type Journal Article
    ISSN 1523-7052
    ISSN (online) 1523-7052
    DOI 10.1021/acs.orglett.4c01149
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  5. Article ; Online: NCα-gem-dimethylated peptoid side chains: A novel approach for structural control and peptide sequence mimetics.

    Shyam, Radhe / Nauton, Lionel / Angelici, Gaetano / Roy, Olivier / Taillefumier, Claude / Faure, Sophie

    Biopolymers

    2019  Volume 110, Issue 6, Page(s) e23273

    Abstract: The design of linear peptoid oligomers adopting well-defined secondary structures while mimicking defined peptide primary sequences is a major challenge in the context of drug discovery. To this end, chemists have developed cis-inducing peptoid side ... ...

    Abstract The design of linear peptoid oligomers adopting well-defined secondary structures while mimicking defined peptide primary sequences is a major challenge in the context of drug discovery. To this end, chemists have developed cis-inducing peptoid side chains to build robust polyproline type I helices. However, the number of efficient examples remains scarce and chemical diversity accessible through the use of these side chains is limited. Herein, we introduce an array of NCα-gem-dimethylated peptoid residues mimicking proteinogenic amino acids. Submonomer synthesis and block-coupling approaches were explored to access heterooligomers incorporating these novel types of side chains. NMR studies of monomer and trimer models showed that the NCα-gem-dimethylated groups exert complete cis control on the backbone amide conformation. Lastly, a preliminary molecular modeling study gave an insight into the preferred orientation of the substituents of the NCα-gem-dimethyl side chains relative to the peptoid backbone.
    MeSH term(s) Amines/chemistry ; Amino Acid Sequence ; Isomerism ; Methylation ; Molecular Dynamics Simulation ; Nuclear Magnetic Resonance, Biomolecular ; Peptides/chemistry ; Peptoids/chemistry ; Protein Structure, Secondary
    Chemical Substances Amines ; Peptides ; Peptoids
    Language English
    Publishing date 2019-03-21
    Publishing country United States
    Document type Journal Article
    ZDB-ID 1123-x
    ISSN 1097-0282 ; 0006-3525
    ISSN (online) 1097-0282
    ISSN 0006-3525
    DOI 10.1002/bip.23273
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  6. Article: 1,2,3-Triazolium-Based Peptoid Oligomers

    Aliouat, Hafida / Caumes Cécile / Faure Sophie / Roy Olivier / Taillefumier Claude / Zouikri Mohamed

    Journal of organic chemistry. 2017 Mar. 03, v. 82, no. 5

    2017  

    Abstract: The cis-directing effect of the 1,2,3-triazolium-type side chain was studied on dimeric peptoid models with various patterns: αα, αβ, βα and ββ. Low influences of the sequence and of the solvent were observed, the cis conformation of the amide ... ...

    Abstract The cis-directing effect of the 1,2,3-triazolium-type side chain was studied on dimeric peptoid models with various patterns: αα, αβ, βα and ββ. Low influences of the sequence and of the solvent were observed, the cis conformation of the amide carrying the triazolium ranging from 83 to 94% in proportion. The synthesis of peptoid homooligomers with four or eight pendant 1,2,3-triazolium side chains is described. α-, β- and α,β-peptoids carrying propargyl groups were subjected to CuAAC reaction using alkyl azides, and the resulting triazoles were quaternized providing well-defined multitriazolium platforms. The influence of the counteranion (PF₆–, BF₄– or I–) on the conformation was also studied.
    Keywords azides ; chemical reactions ; models ; moieties ; organic chemistry ; solvents ; triazoles
    Language English
    Dates of publication 2017-0303
    Size p. 2386-2398.
    Publishing place American Chemical Society
    Document type Article
    ZDB-ID 123490-0
    ISSN 1520-6904 ; 0022-3263
    ISSN (online) 1520-6904
    ISSN 0022-3263
    DOI 10.1021%2Facs.joc.6b02804
    Database NAL-Catalogue (AGRICOLA)

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  7. Article: Homogeneous and Robust Polyproline Type I Helices from Peptoids with Nonaromatic α-Chiral Side Chains

    Roy, Olivier / Dumonteil Geoffrey / Faure Sophie / Jouffret Laurent / Kriznik Alexandre / Taillefumier Claude

    Journal of the American Chemical Society. 2017 Sept. 27, v. 139, no. 38

    2017  

    Abstract: Peptoids that are oligomers of N-substituted glycines represent a class of peptide mimics with great potential in areas ranging from medicinal chemistry to biomaterial science. Controlling the equilibria between the cis and trans conformations of their ... ...

    Abstract Peptoids that are oligomers of N-substituted glycines represent a class of peptide mimics with great potential in areas ranging from medicinal chemistry to biomaterial science. Controlling the equilibria between the cis and trans conformations of their backbone amides is the major hurdle to overcome for the construction of discrete folded structures, particularly for the development of all-cis polyproline type I (PPI) helices, as tools for modulating biological functions. The prominent role of backbone to side chain electronic interactions (n → π*) and side chains bulkiness in promoting cis-amides was essentially investigated with peptoid aromatic side chains, among which the chiral 1-naphthylethyl (1npe) group yielded the best results. We have explored for the first time the possibility to achieve similar performances with a sterically hindered α-chiral aliphatic side chain. Herein, we report on the synthesis and detailed conformational analysis of a series of (S)-N-(1-tert-butylethyl)glycine (Ns1tbe) peptoid homo-oligomers. The X-ray crystal structure of an Ns1tbe pentamer revealed an all-cis PPI helix, and the CD curves of the Ns1tbe oligomers also resemble those of PPI peptide helices. Interestingly, the CD data reported here are the first for any conformationally homogeneous helical peptoids containing only α-chiral aliphatic side chains. Finally we also synthesized and analyzed two mixed oligomers composed of NtBu and Ns1tbe monomers. Strikingly, the solid state structure of the mixed oligomer Ac-(tBu)2-(s1tbe)4-(tBu)2-COOtBu, the longest to be solved for any linear peptoid, revealed a PPI helix of great regularity despite the presence of only 50% of chiral side chain in the sequence.
    Keywords amides ; biobased products ; crystal structure ; molecular conformation ; N-substituted glycines ; solids
    Language English
    Dates of publication 2017-0927
    Size p. 13533-13540.
    Publishing place American Chemical Society
    Document type Article
    ZDB-ID 3155-0
    ISSN 1520-5126 ; 0002-7863
    ISSN (online) 1520-5126
    ISSN 0002-7863
    DOI 10.1021%2Fjacs.7b07475
    Database NAL-Catalogue (AGRICOLA)

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  8. Article ; Online: 1,2,3-Triazolium-Based Cationic Amphipathic Peptoid Oligomers Mimicking Antimicrobial Helical Peptides.

    Shyam, Radhe / Charbonnel, Nicolas / Job, Aurélie / Blavignac, Christelle / Forestier, Christiane / Taillefumier, Claude / Faure, Sophie

    ChemMedChem

    2018  Volume 13, Issue 15, Page(s) 1513–1516

    Abstract: Amphipathic cationic peptoids (N-substituted glycine oligomers) represent a promising class of antimicrobial peptide mimics. The aim of this study is to explore the potential of the triazolium group as a cationic moiety and helix inducer to develop ... ...

    Abstract Amphipathic cationic peptoids (N-substituted glycine oligomers) represent a promising class of antimicrobial peptide mimics. The aim of this study is to explore the potential of the triazolium group as a cationic moiety and helix inducer to develop potent antimicrobial helical peptoids. Herein we report the first solid-phase synthesis of peptoid oligomers incorporating 1,2,3-triazolium-type side chains and their evaluation against Escherichia coli, Enterococcus faecalis, and Staphylococcus aureus. Several triazolium-based oligomers, even of short length, selectively kill bacteria over mammalian cells. SEM visualization of S. aureus cells treated with a dodecamer and a hexamer reveals severe cell membrane damage and suggests that the longer oligomer acts by pore formation.
    MeSH term(s) Antimicrobial Cationic Peptides/chemistry ; Circular Dichroism ; Enterococcus faecalis/drug effects ; Escherichia coli/drug effects ; Microbial Sensitivity Tests ; Microscopy, Electron, Scanning ; Molecular Mimicry ; Peptoids/chemistry ; Polymers/chemistry ; Staphylococcus aureus/drug effects ; Triazoles/chemistry ; Triazoles/pharmacology
    Chemical Substances Antimicrobial Cationic Peptides ; Peptoids ; Polymers ; Triazoles
    Language English
    Publishing date 2018-07-04
    Publishing country Germany
    Document type Journal Article ; Research Support, Non-U.S. Gov't
    ZDB-ID 2218496-X
    ISSN 1860-7187 ; 1860-7179
    ISSN (online) 1860-7187
    ISSN 1860-7179
    DOI 10.1002/cmdc.201800273
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  9. Article ; Online: Topologically Diverse Shapes Accessible by Modular Design of Arylopeptoid Macrocycles.

    Hjelmgaard, Thomas / Nauton, Lionel / De Riccardis, Francesco / Jouffret, Laurent / Faure, Sophie

    Organic letters

    2018  Volume 20, Issue 1, Page(s) 268–271

    Abstract: N-Substituted aromatic cyclooligoamides composed of different combinations of ortho-, meta-, and/or para-arylopeptoid residues carrying methoxyethyl side chains have been efficiently synthesized by macrocyclization of the corresponding linear oligomers. ... ...

    Abstract N-Substituted aromatic cyclooligoamides composed of different combinations of ortho-, meta-, and/or para-arylopeptoid residues carrying methoxyethyl side chains have been efficiently synthesized by macrocyclization of the corresponding linear oligomers. The study of the architectures of these macrocycles in solution and solid state has revealed that tetracyclic arylopeptoids adopt sequence-dependent shapes with different backbone amide conformations and side-chain orientations. Remarkably, despite the absence of intramolecular H-bonding ability, some of these arylopeptoid macrocycles show well-defined architectures in solution.
    Language English
    Publishing date 2018--05
    Publishing country United States
    Document type Journal Article ; Research Support, Non-U.S. Gov't
    ISSN 1523-7052
    ISSN (online) 1523-7052
    DOI 10.1021/acs.orglett.7b03660
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  10. Article: Human excellence and governance

    Faure, Sophie / Tollet, Françoise

    Handbook of top management teams , p. 338-351

    the Confucius challenge

    2010  , Page(s) 338–351

    Author's details Sophie Faure and Françoise Tollet
    Language English
    Size graph. Darst.
    Publisher Palgrave Macmillan
    Publishing place Basingstoke [u.a.]
    Document type Article
    ISBN 0-230-21859-8 ; 978-0-230-21859-8
    Database ECONomics Information System

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