Iron(III) chloride

Summary

Iron(III) chloride describes the inorganic compounds with the formula (H2O)x. Also called ferric chloride, these compounds are available both in anhydrous and hydrated forms which are both hygroscopic. They are common sources of iron in its +3 oxidation state. The anhydrous derivative is a Lewis acid, while the hydrate is a mild oxidizing agent. It is used as a water cleaner and as an etchant for metals. Structure and properties All forms of ferric chloride are paramagnetic, owing to the presence of five unpaired electrons residing in 3d orbitals. This electronic configuration places electrons in molecular orbitals that are antibonding with respect to ligands. Thus, iron(III) chlorides are labile, undergoing rapid ligand exchange in solution. In contrast to their kinetic lability, iron(III) chlorides are thermodynamically robust, as reflected by the vigorous methods applied to their synthesis. Anhydrous The anhydrous com

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[4+2]-Annulations of Aminocyclobutanes

Florian Patrick Marie Daniel De la Barre De Nanteuil, Daniele Perrotta, Sophie Lucie Racine, Jérémy Vuilleumier, Jérôme Waser

The first [4 + 2]-annulation between aminocyclobutanes and aldehydes to access tetrahydropyranyl amines is reported. With phthalimido cyclobutane dicarboxylates and aromatic aldehydes, tetrahydropyrans were obtained in 53-92% yield and 3:1-17:1 dr using scandium triflate or iron trichloride as catalyst. The use of thymine- or fluorouracil-substituted cyclobutanes gave direct access to six-membered ring nucleoside analogues. Finally, the [4 + 2]-annulation between aminocyclobutanes and enol ethers led to the corresponding cyclohexylamines.

American Chemical Society2015

Peptides represent a promising molecular class for drug development. They combine several strengths of small molecules (e.g. efficient tissue diffusion, low immunogenicity and access to chemical synthesis) and key properties of biologics such as monoclonal antibodies (e.g. high affinity and specificity). Most of the peptide drugs are natural products or derivatives thereof, as for example human peptide hormones or antibacterial peptides. In recent years, a range of methodologies were established to develop peptides binding to therapeutic targets de novo. Our laboratory is specialized on the in vitro evolution of bicyclic peptides by phage display. Bicyclic peptides have two macrocyclic rings that allow for binding protein targets with high affinity and selectivity. The aim of my thesis was to improve the potency, selectivity and stability of phage-selected bicyclic peptide inhibitors of coagulation factor XII (FXII) and matrix metalloproteinase 2 (MMP-2), and to test their therapeutic potential in vivo. Specifically, I planned at improving the bicyclic peptides by substituting natural amino acids with unnatural ones. As described in the following, the substitutions to unnatural amino acids had led to substantial improvements in the bicyclic peptides, and this had enabled me the evaluation of the inhibitors in disease models. In my first and second project, I aimed at improving the potency and stability of a bicyclic peptide FXII inhibitor that was previously developed in our lab by phage display, and to test the therapeutic potential of the resulting peptide in vivo. FXII has recently been identified as a promising target for safe anticoagulation therapy. In the first project, I investigated if the insertion of a single carbon atom into the macrocyclic backbone of a bicyclic peptide FXII inhibitor can improve its binding affinity. Positions within the macrocycle susceptible to atom insertion were first identified using a scanning methodology where glycine mutants were compared to ¿-alanine mutants. Upon insertion of atoms in the backbone using ¿-amino acids or homologated cysteine analogues, two peptides showed 4.7- and 2.5-fold improved Ki values. The better one blocked FXII with a Ki of 1.5 ± 0.1 nM and was more potent than the lead peptide in inhibiting the activation of the intrinsic coagulation pathway. The strategy of ring size variation by one or several atoms should be generally applicable for the affinity maturation of in-vitro-evolved cyclic peptides. In my second project, I aimed at improving further the potency of the bicyclic peptide FXII inhibitor described before, and to additionally improve its proteolytic stability. I achieved both these goals by replacing further natural amino acids to unnatural ones. Sub-nanomolar activity for human and mouse FXII (370 and 450 pM respectively) as well as a high stability (t1/2 > 128 ± 8 h in plasma) permitted preclinical evaluation of the peptide. The inhibitor efficiently blocked intrinsic coagulation in blood plasma from human, mouse and rabbit. I further demonstrated that the peptide reduced experimental thrombosis induced by ferric chloride in mice and suppressed blood coagulation in artificial lungs in rabbits, all without increasing the risk of bleeding. This shows that the optimized bicyclic peptide is a promising candidate for thromboprotection in various medical conditions. In a third project, I aimed at improving the potency and stability of a bicyclic peptide MMP-2 inhibi

EPFL2018

Print-Light-Synthesis of Ni and NiFe-nanoscale catalysts for oxygen evolution

Victor Costa Bassetto, Hubert Girault, Andreas Stephan Lesch, Mounir Driss Mensi, Emadeddin Oveisi

By hyphenating inkjet printing and flash light irradiation, Ni- and NiFe-nano-electrocatalysts of diameters below 2.5 nm with ultralow loadings below 2 µg·cm–2 are synthesized. To achieve this, nanoliter ink volumes containing Ni and Fe chlorides as catalyst precursors are rapidly printed on large-scale carbon nanotube-coated glassy carbon electrodes and exposed to millisecond-long high intensity light pulses from a Xenon flash lamp. The carbon nanotube coating acts as light-to-heat absorber generating surface peak temperatures of several hundred degrees. The light-induced reduction of the Ni and Fe precursors into chloride-free mixed metal composites is facilitated by alcohols that act as sacrificial electron donors in the printed precursor films. Besides the merging of large-scale electrode production and nanoparticle synthesis into a single robust and rapid process, the adjustability of the precursor ratios using parallel printheads, the operation under ambient conditions, the absence of capping agents as well as surfactants, and the up-scalability to industrial levels are the major advantages of this new electrode fabrication method. Furthermore, the process is superior to standard lab-scale electrocatalyst deposition methods, such as drop casting, and is more flexible to control compared to hydro- and solvothermal syntheses. The electrochemical characterisation of the Ni- and NiFe-based nano-electrocatalysts by voltammetric cycling leads to onset potentials as low as 240 mV (at 0.1 mA·cm–2), overpotentials of 334 mV (at 10 mA·cm–2), Tafel slopes of 41 mV·dec–1 and high turnover frequencies of up to 4.5 s–1 for the oxygen evolution reaction.

2019

EPFL2018