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Personne :
Biron, Éric

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Biron

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Éric

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Université Laval. Faculté de pharmacie

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ncf11849118

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Voici les éléments 1 - 4 sur 4
  • PublicationAccès libre
    Synthesis, antimicrobial activity and conformational analysis of the class IIa bacteriocin pediocin PA-1 and analogs thereof
    (Springer Nature, 2018-06-13) Biron, Éric; Fliss, Ismaïl; Bédard, François; Rebuffat, Sylvie; Menétrey, Séverine; Hammami, Riadh
    The antimicrobial peptide pediocin PA-1 is a class IIa bacteriocin that inhibits several clinically relevant pathogens including Listeria spp. Here we report the synthesis and characterization of whole pediocin PA-1 and novel analogs thereof using a combination of solid- and solution-phase strategies to overcome difficulties due to instability and undesired reactions. Pediocin PA-1 thus synthesized was a potent inhibitor of Listeria monocytogenes (MIC = 6.8 nM), similar to the bacteriocin produced naturally by Pediococcus acidilactici. Of particular interest is that linear analogs lacking both of the disulfide bridges characterizing pediocin PA-1 were as potent. One linear analog was also a strong inhibitor of Clostridium perfringens, another important food-borne pathogen. These results are discussed in light of conformational information derived from circular dichroism, solution NMR spectroscopy and structure-activity relationship studies.
  • PublicationAccès libre
    N-Substituted arylsulfonamide building blocks as alternative submonomers for peptoid synthesis
    (Elsevier, 2015-01-08) Biron, Éric; Derson, Antoine; Vézina-Dawod, Simon
    Peptoids (oligo N-substituted glycines) are peptidomimetic oligomers showing attractive structural and pharmacological properties. The efficiency of their synthesis has prompted the use of peptoids in combinatorial libraries. To increase the chemical diversity accessible in peptoid design and libraries, we demonstrate here that N-substituted o-nitrobenzenesulfonamide derivatives can be used as alternative building blocks in the synthesis of peptoids by the submonomer approach. The preparation of N,O-protected amino alcohol submonomers and the conditions for their incorporation into peptoid oligomers are reported. The described method is compatible with the submonomer approach and was applied to prepare peptoid oligomers bearing different hydroxylated side chains.
  • PublicationAccès libre
    Preparation of N-substituted N-arylsulfonylglycines and their use in peptoid synthesis
    (American Chemical Society, 2015-11-09) Biron, Éric; Jobin, Steve; Herby, Claire; Vézina-Dawod, Simon; Derson, Antoine
    To increase the chemical diversity accessible with peptoids and peptide–peptoid hybrids, N-alkylated arylsulfonamides were used to prepare side chain protected N-substituted glycines compatible with solid-phase synthesis. The described procedures give access to peptoid monomers bearing a wide variety of functional groups from commercially available amines in four straightforward steps. The prepared N-substituted N-arylsulfonylglycines were used as monomers in solid-phase synthesis to introduce relevant functionalized side chains into peptoid oligomers and peptide–peptoid hybrids.
  • PublicationAccès libre
    One-pot photochemical ring-opening/cleavage approach for the synthesis and decoding of cyclic peptide libraries
    (American Chemical Society, 2016-02-25) Biron, Éric; Porte, Karine; Vézina-Dawod, Simon; Bédard, François; Liang, Xinxia
    A novel dual ring-opening/cleavage strategy to determine the sequence of cyclic peptides from one bead, one compound libraries is described. The approach uses a photolabile residue within the macrocycle and as a linker to allow a simultaneous ring opening and cleavage from the beads upon UV irradiation and provide linearized molecules. Cyclic peptides of five to nine residues were synthesized and the generated linear peptides successfully sequenced by tandem mass spectrometry.