Strengthening Peptoid Helicity through Sequence Site-Specific Positioning of Amide cis-Inducing NtBu Monomers
| Autor: | Claude Taillefumier, Olivier Roy, Maha Rzeigui, Laurent Jouffret, Mounir Traïkia, Jameleddine Khiari, Alexandre Kriznik |
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| Přispěvatelé: | Institut de Chimie de Clermont-Ferrand (ICCF), SIGMA Clermont (SIGMA Clermont)-Institut de Chimie du CNRS (INC)-Université Clermont Auvergne [2017-2020] (UCA [2017-2020])-Centre National de la Recherche Scientifique (CNRS), SIGMA Clermont (SIGMA Clermont), Université de Carthage - University of Carthage, Ingénierie Moléculaire et Physiopathologie Articulaire (IMoPA), Université de Lorraine (UL)-Centre National de la Recherche Scientifique (CNRS), Ingénierie, Biologie et Santé en Lorraine (IBSLor), Institut National de la Santé et de la Recherche Médicale (INSERM)-Université de Lorraine (UL)-Centre National de la Recherche Scientifique (CNRS), GONNET, JULIE, Université de Lorraine (UL)-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS) |
| Rok vydání: | 2019 |
| Předmět: |
010405 organic chemistry
Peptidomimetic Stereochemistry Organic Chemistry [SDV.BBM.BM]Life Sciences [q-bio]/Biochemistry Molecular Biology/Molecular biology Sequence (biology) Peptoid [SDV.BBM.BM] Life Sciences [q-bio]/Biochemistry Molecular Biology/Molecular biology 010402 general chemistry 01 natural sciences 0104 chemical sciences Folding (chemistry) chemistry.chemical_compound Monomer chemistry [SDV.BBM.GTP]Life Sciences [q-bio]/Biochemistry Molecular Biology/Genomics [q-bio.GN] Amide Side chain [SDV.BBM.GTP] Life Sciences [q-bio]/Biochemistry Molecular Biology/Genomics [q-bio.GN] Polyproline helix |
| Zdroj: | Journal of Organic Chemistry Journal of Organic Chemistry, 2020, 85 (4), pp.2190-2201. ⟨10.1021/acs.joc.9b02916⟩ Journal of Organic Chemistry, American Chemical Society, 2020, ⟨10.1021/acs.joc.9b02916⟩ |
| ISSN: | 1520-6904 0022-3263 |
| DOI: | 10.1021/acs.joc.9b02916 |
| Popis: | International audience; The synthesis of biomimetic helical secondary structures is sought after for the construction of innovative nanomaterials and applications in medicinal chemistry such as the development of protein-protein interaction modulators. Peptoids, a sequence-defined family of oligomers, enable a peptidomimetic strategy, especially considering the easily accessible monomer diversity and peptoid helical folding propensity. However, cis-trans isomerization of the backbone tertiary amides may impair the peptoid's adoption of stable secondary structures, notably the all-cis polyproline I-like helical conformation. Here, we show that cis-inducing NtBu achiral monomers strategically positioned within chiral sequences may reinforce the degree of peptoid helicity, although with a reduced content of chiral side chains. The design principles presented here will undoubtedly help achieve more conformationally stable helical peptoids with desired functions. |
| Databáze: | OpenAIRE |
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