Article
Chemistry, Multidisciplinary
Valentina Corvaglia, Florian Sanchez, Friedericke S. Menke, Celine Douat, Ivan Huc
Summary: Helically folded oligoamides composed of up to 41 units were efficiently prepared using optimized manual solid-phase synthesis (SPS) protocols. The high yield and purity of the products, as well as the validation of analytical methods including H-1 NMR, contribute to the efficiency of these protocols. Implementation of SPS on a commercial peptide synthesizer through in situ acid chloride activation under Appel's conditions dramatically reduces the labor required for producing long sequences, representing a breakthrough for the development of helical aromatic oligoamide foldamers.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Multidisciplinary
Yulong Zhong, Thomas A. Sobiech, Brice Kauffmann, Bo Song, Xiaopeng Li, Yann Ferrand, Ivan Huc, Bing Gong
Summary: Two aromatic oligoamides, H8 and H16, were found to wrap around octyl viologen (OV2+) and para-bis(trimethylammonium)benzene (TB2+) to form 2:2 and 1:2 complexes, respectively. The longer H16 exhibited higher binding affinity with OV2+ and showed negative cooperativity. Interestingly, H16 selectively bound OV2+ over TB2+. This study highlights the pairwise placement of OV2+ ions, negative cooperativity, and the adaptability of hosts and guests, resulting in stable [2]-, [3]-, and [4]pseudo-foldaxanes.
Review
Chemistry, Multidisciplinary
Ayman Akhdar, Arnaud Gautier, Thomas Hjelmgaard, Sophie Faure
Summary: This review discusses the characteristics, synthetic pathways, and foldameric properties of N-alkylated aromatic poly- and oligoamides, with detailed descriptions of representative members.
Article
Chemistry, Multidisciplinary
Francois Kerff, Cui-Lian Liu, Xiao Mu, Ugo Gilbert, Louis Smal, Loic Meinertzhagen, Brice Kauffmann, Koen Robeyns, Michael L. Singleton
Summary: The synthesis of a range of three-dimensional heteroaromatic monomers suitable for the synthesis of aromatic oligoamide foldamers has been described in this study. The newly developed motif orients the two heterocyclic rings and attached groups at an angle of approximately 120 degrees, providing new geometric considerations for the design of this class of foldamers.
Article
Chemistry, Multidisciplinary
Albano Galan, Kristijan Lulic, Jingqi Wang, Barbara Wicher, Ivan Huc, Jean Duhamel, Victor Maurizot
Summary: Deprotonation of acid-terminated helical aromatic foldamers with a mineral base in chlorinated solvents resulted in their dimerization through the coordination of a metal cation (Li+, Na+, K+, Ag+, or Hg2+) with the terminal carboxylate functions. This novel ligation method was utilized for the oligomerization of diacid-functionalized foldamers.
CHEMICAL COMMUNICATIONS
(2023)
Review
Chemistry, Multidisciplinary
Tim Seedorf, Andreas Kirschning, Danny Solga
Summary: The term privileged structure refers to a single molecular substructure or scaffold that can serve as a starting point for high-affinity ligands for more than one receptor type. In this study, aromatic oligoamides, with well-defined scaffolds capable of specifically binding to biomacromolecules, have been identified as a group of privileged substructures. These oligoamides, including cystobactamids, albicidin, distamycin A, netropsin, have been shown to inhibit protein-protein and nucleic acid-protein interactions. This report is the first to consolidate scattered knowledge about aromatic oligoamides in connection with biomedical applications.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Chemistry, Multidisciplinary
Nagendar Pendem, Yella-Reddy Nelli, Leonie Cussol, Claude Didierjean, Brice Kauffmann, Christel Dolain, Gilles Guichard
Summary: Oligomers with a helix-turn-helix super-secondary structure were prepared by covalently bridging aliphatic oligourea foldamer helices with either rigid aromatic or flexible aliphatic spacers. The relative orientation of the helices in these dimers was studied using high-resolution X-ray diffraction analysis. Racemic crystallography was employed in some cases to facilitate crystallization and structure determination. All structures were solved using direct methods. Well-defined parallel helical hairpin motifs were observed in all cases when 4,4'-methylene diphenyl diisocyanate was used as a dimerizing agent, regardless of the primary sequence and chain length.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Review
Chemistry, Organic
Aizhan Abdildinova, Mark J. Kurth, Young-Dae Gong
Summary: Peptidomimetics are compounds with promising pharmacological properties that overcome limitations of peptides through backbone modifications. Accessible synthetic methodologies play a key role in peptidomimetic progress, with solid-phase organic synthesis serving as a powerful tool for their preparation. Numerous strategies for peptide backbone modifications via solid-phase synthesis have been developed in the last two decades.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Xiaosheng Yan, Peimin Weng, Di Shi, Yun-Bao Jiang
Summary: This feature article discusses the emergence of supramolecular helices built from helical building blocks, highlighting the importance of efficient propagation of helicity during assembly for favoring homochirality and channel functions.
CHEMICAL COMMUNICATIONS
(2021)
Article
Polymer Science
Bao-Rui Gao, Yong-Jie Wu, Lei Xu, Hui Zou, Li Zhou, Na Liu, Zong-Quan Wu
Summary: Helical polycarbenes with optical activity were designed and synthesized in an environmentally friendly manner. These polymers exhibited stable helical conformations with preferred handedness and showed efficient chiral separation ability.
Article
Chemistry, Multidisciplinary
Geunmoo Song, Kyung Mog Kim, Seungwon Lee, Kyu-Sung Jeong
Summary: Aromatic helical receptors P-1 and P-2 were modified slightly by aerobic oxidation to produce new receptors P-7 and P-8 with right-handed helical cavities, which led to significant changes in binding properties for chiral guests. Subtle post-modifications of the synthetic receptors were shown to significantly alter their binding affinities and selectivities, especially for guests with long and flexible chains.
CHEMISTRY-AN ASIAN JOURNAL
(2021)
Article
Chemistry, Multidisciplinary
Debabrata Maity, Andrew D. Hamilton
Summary: The metal-free and achiral tri-pyridylamide foldamer, DM 11, with a critical naphthalimide side chain, self-assembles in a left-handed helical manner in the presence of chiral adenosine phosphates under physiological conditions, showing a very high degree of helicity compared to other nucleoside phosphates, including ATP.
CHEMICAL COMMUNICATIONS
(2021)
Review
Food Science & Technology
Shan Wang, Yue Li, Chaoyang Ma, Dejian Huang, Shangwei Chen, Zhu Song, Wang Hongxin
Summary: The poor lipophilicity and instability of water-soluble polyphenols limit their application in food, but due to their multiple biological activities, attention has been given to improving their lipophilicity and stability. This review presents the enzymatic biosynthesis of lipophilic derivatives of water-soluble polyphenols and analyzes the effects of reaction factors on the structure and bioactivities of the derivatives.
CRITICAL REVIEWS IN FOOD SCIENCE AND NUTRITION
(2022)
Article
Chemistry, Organic
Pablo Tovillas, Claudio D. Navo, Paula Oroz, Alberto Avenoza, Francisco Corzana, Maria M. Zurbano, Gonzalo Jimenez-Oses, Jesus H. Busto, Jesus Peregrina
Summary: Chiral bicyclic N,O-acetal isoserine derivatives have been synthesized using acid-catalyzed reactions, which have significant applications in peptidomimetic and medicinal chemistry.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Engineering, Chemical
Jiangyi Wu, Youfang Huang, Xiaojia Huang
Summary: An efficient method using electroenhanced solid phase microextraction (EE-SPME) with porous monolith doped with carboxylic carbon nanotubes (M@CCNs) was developed to trap polar aromatic amines (AAs) in water samples. The introduction of M@CCNs and application of electric field during the extraction process significantly improved the trap performance, with extraction efficiencies increasing by 36-48% compared to traditional methods. The method was demonstrated to be practical and reliable for quantifying AAs in water samples, with recoveries ranging from 83.1% to 118%.
SEPARATION AND PURIFICATION TECHNOLOGY
(2022)
Article
Environmental Sciences
M. Philippe, P. Le Pape, E. Resongles, G. Landrot, R. Freydier, L. Bordier, B. Baptiste, L. Delbes, C. Baya, C. Casiot, S. Ayrault
Summary: Although antimony (Sb) contamination in urban areas is well-documented, there are still knowledge gaps regarding the sources and chemical forms of Sb in urban environments. This study focused on the fate of metallic contaminants emitted by non-exhaust road traffic in urban aquatic systems. The results showed that Sb enrichment was higher compared to other traffic-related contaminants, and the speciation of Sb varied with redox conditions. The presence of Sb-containing brake pad residues was also found. These findings highlight the importance of traffic emissions as a specific source of Sb in surface environments.
Article
Materials Science, Multidisciplinary
Anthony Durand, Denis Sornin, Olivier Tache, Thomas Guilbert, Francois Brisset, Ludovic Delbes, Benoit Baptiste, Thierry Baudin, Roland Loge
Summary: The development of generation IV nuclear reactors necessitates improvements in structural and cladding materials. Oxide dispersion strengthened (ODS) steels, specifically the martensitic and ferritic ODS steels, show promise due to their enhanced creep properties. However, the presence of untransformed ferrite (UF) phase at high temperatures in certain martensitic ODS steels, which is unexpected according to experimental observation and thermodynamic calculations, presents an interesting opportunity to improve creep resistance. This study focuses on the thermal stability of UF in a martensitic ODS steel with 10 wt% Cr, investigating the effects of heat treatments on UF fraction evolution and microstructural changes.
JOURNAL OF NUCLEAR MATERIALS
(2023)
Article
Chemistry, Multidisciplinary
Valentina Corvaglia, Florian Sanchez, Friedericke S. Menke, Celine Douat, Ivan Huc
Summary: Helically folded oligoamides composed of up to 41 units were efficiently prepared using optimized manual solid-phase synthesis (SPS) protocols. The high yield and purity of the products, as well as the validation of analytical methods including H-1 NMR, contribute to the efficiency of these protocols. Implementation of SPS on a commercial peptide synthesizer through in situ acid chloride activation under Appel's conditions dramatically reduces the labor required for producing long sequences, representing a breakthrough for the development of helical aromatic oligoamide foldamers.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Physics, Fluids & Plasmas
C. Douat, S. Ponduri, T. Boumans, O. Guaitella, S. Welzel, E. Carbone, R. Engeln
Summary: This study investigates the dissociation of CO2 in a symmetric pin-to-pin dielectric barrier discharge (DBD). The number of filaments per half cycle follows a power-law as a function of the injected power and remains constant regardless of pressure or other process parameters. The CO2 conversion is found to be proportional to specific energy input (SEI) even at the single filament level.
PLASMA SOURCES SCIENCE & TECHNOLOGY
(2023)
Article
Chemistry, Multidisciplinary
Andy W. Heard, Nicolas Dauphas, Isaac L. Hinz, Jena E. Johnson, Marc Blanchard, Esen E. Alp, Michael Y. Hu, Jiyong Zhao, Barbara Lavina, Mark E. Fornace, Justin Y. Hu, Mathieu Roskosz, Corliss Kin Sio, Nicole X. Nie, Benoit Baptiste
Summary: Iron formations (IFs) are chemical sedimentary rocks formed before the Great Oxidation Event. The traditional model suggests that hydrated Fe3+ oxides (HFOs) precipitated from Fe2+-rich, anoxic deep waters, while an alternative model proposes anoxic ferrous silicate precipitation. This study investigates the Fe isotopic fractionation of greenalite and ferrihydrite and suggests that ferrous greenalite can produce the pre-GOE Fe isotopic compositions, challenging the assumption that heavy Fe isotopic enrichments are solely indicative of primary IF mineralogies.
ACS EARTH AND SPACE CHEMISTRY
(2023)
Letter
Geochemistry & Geophysics
J. -c. Viennet, M. Roskosz, T. Nakamura, P. Beck, B. Baptiste, B. Lavina, E. E. Alp, M. Y. Hu, J. Zhao, M. Gounelle, R. Brunetto, H. Yurimoto, T. Noguchi, R. Okazaki, H. Yabuta, H. Naraoka, K. Sakamoto, S. Tachibana, T. Yada, M. Nishimura, A. Nakato, A. Miyazaki, K. Yogata, M. Abe, T. Okada, T. Usui, M. Yoshikawa, T. Saiki, S. Tanaka, F. Terui, S. Nakazawa, S. -i. Watanabe, Y. Tsuda
Summary: The Hayabusa 2 spacecraft returned grains of the Ryugu carbonaceous asteroid, which represent pristine CI chondritic materials preserved from Earth's atmosphere. Evidence of organics trapped within smectite layers in Ryugu grains is shown, whereas no such organics are found in the Orgueil CI meteorite. We propose that the organics within smectite interlayers in the Orgueil CI meteorite were lost during oxidation on Earth. Additionally, we suggest that the presence of organics within smectite interlayers might be related to the observed NH infrared signature in Ryugu particles and a few large C-type asteroids including Ceres.
GEOCHEMICAL PERSPECTIVES LETTERS
(2023)
Article
Nuclear Science & Technology
S. Klotz, D. Hrabovski, E. Lelievre-Berna, B. Baptiste
Summary: Null-scattering Ti:Zr alloy is widely used in neutron scattering experiments because it does not produce contaminant Bragg reflections. We report the discovery of superconductivity in this material, with a critical temperature of 1.4 K and critical magnetic fields of approximately 100 Oe and 4500 Oe. These properties are not affected by the presence of a small quantity of ferromagnetic iron.
JOURNAL OF NEUTRON RESEARCH
(2023)
Article
Chemistry, Multidisciplinary
Sebastian Dengler, Ryan T. Howard, Vasily Morozov, Christos Tsiamantas, Wei-En Huang, Zhiwei Liu, Christopher Dobrzanski, Vojislava Pophristic, Sophie Brameyer, Celine Douat, Hiroaki Suga, Ivan Huc
Summary: Expanding the chemical diversity of peptide macrocycle libraries through the inclusion of a large aromatic helical foldamer has been implemented. A hybrid macrocyclic nanomolar binder to the C-lobe of the E6AP HECT domain was selected, and its crystal structure and molecular dynamics simulations revealed an intriguing reciprocal helical folding of the peptide and foldamer. The results represent a significant extension in the chemical space amenable to display selection and highlight the potential benefits of incorporating an aromatic foldamer into a peptide macrocycle for protein recognition.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Physical
Frederico G. G. Alabarse, Benoit Baptiste, Yoann Guarnelli, Boby Joseph, Julien Haines
Summary: The behavior of porous aluminophosphate AlPO(4)-17 with a hexagonal ionite structure was studied under high pressure using single-crystal and powder X-ray diffraction. In the presence of nitrogen, oxygen, and argon as pressure transmitting media, the guest species were found to enter the pores of AlPO(4)-17, thereby modifying its properties. The collapse and amorphization of AlPO(4)-17 under pressure were suppressed, and the compressibility was reduced due to the insertion of guest molecules. A phase transition to a new hexagonal structure with cell doubling along the a direction was also observed at pressures above 4.4 GPa in the presence of oxygen.
JOURNAL OF PHYSICAL CHEMISTRY C
(2023)
Article
Physics, Condensed Matter
Amirreza Hemmatzade, Elena Medina, Ludovic Delbes, Benoit Baptiste, David Hrabovsky, Yannick Klein, Steven D. Conradson, Maarit Karppinen, Andrea Gauzzi
Summary: In this study, the structural and superconducting properties of Cu0.75Mo0.25Sr2YCu2O7 +x powder samples oxygenated under high pressure using different concentrations of KClO3 were investigated to understand the unusual superconducting properties in the strongly overdoped region of cuprates. The results showed that the purity of the samples was high and the Tc values remained constant despite varying KClO3 concentrations, suggesting a scenario of Tc saturation. It was hypothesized that overdoping enhances the density of unpaired holes, supported by observed large values of the Sommerfeld coefficient, indicating electronic phase separation between normal and superconducting holes.
Article
Chemistry, Multidisciplinary
Marie E. Perrin, Bo Li, Johanne Mbianda, May Bakail, Christophe Andre, Gwenaelle Moal, Pierre Legrand, Virginie Ropars, Celine Douat, Francoise Ochsenbein, Gilles Guichard
Summary: In this study, we investigated the substitution of 4 α-residues with 3-urea segments in a short α-helical peptide known to bind ASF1. By analyzing the effects of different foldamer replacements, we discovered new binding modes for the peptide-urea chimeras with ASF1.
CHEMICAL COMMUNICATIONS
(2023)
Article
Mineralogy
Karina P. P. Marques, Thierry Allard, Cecile Gautheron, Benoit Baptiste, Rosella Pinna-Jamme, Guillaume Morin, Ludovic Delbes, Pablo Vidal-Torrado
Summary: Interpreting the ages of supergene mineralogical phases in laterite is complex due to the polycrystalline mixtures and different crystalization epochs. This study proposes a methodology for performing detailed mineralogical analysis of hematite and goethite single grains prior to their dating using the (U-Th)/He method. Using X-ray diffraction patterns obtained from XRD_rotat and XRD_synch, the XRD_rotat approach can be validated for analyzing undisturbed grains and subsequent dating.
EUROPEAN JOURNAL OF MINERALOGY
(2023)
Article
Chemistry, Organic
Binhao Teng, Joan Atcher, Lars Allmendinger, Celine Douat, Yann Ferrand, Ivan Huc
Summary: Aromatic oligoamide foldamers were designed to fold into helical structures through local conformation preferences and solvophobic effects. Solid phase synthesis allowed for efficient synthesis of the desired sequences. Solvent-driven conformational transitions of the foldamers were observed using NMR and UV absorption spectroscopy, varying with sequence length.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Binhao Teng, Pradeep K. Mandal, Lars Allmendinger, Celine Douat, Yann Ferrand, Ivan Huc
Summary: This study designed and synthesized water-soluble helically folded aromatic oligoamides. By replacing charged side chains with neutral methoxy groups, various aggregates were formed and studied using different experimental methods. The results showed that the hydrophobic effect was the main driving force for aggregation and could be finely modulated by the presence or absence of charges.
Article
Chemistry, Multidisciplinary
John Brown, Juan Forero-Saboya, Benoit Baptiste, Martin Karlsmo, Gwenaelle Rousse, Alexis Grimaud
Summary: This study investigates a design principle for aqueous battery electrolytes by combining chaotropic ions and imide anions to form GdmTFSI salt. The study reveals that GdmTFSI salt disrupts the hydrogen bonding network of aqueous solutions, reducing water reactivity and expanding the electrochemical stability window.
CHEMICAL COMMUNICATIONS
(2023)