CHIMIE ORGANIQUE EXERCICES RSOLUS PAUL ARNAUD PDF

Jamart, Brigitte Overview. Publication Timeline. Most widely held works by Brigitte Jamart. Chimie organique : les cours de Paul Arnaud by Paul Arnaud 1 edition published in in French and held by 21 WorldCat member libraries worldwide. By extrapolating an original strategy of hydrazinoacids synthesis developed in the LCPM we were able to obtain N-aminodipeptides in high optical purity in a satisfactory way.

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Jamart, Brigitte Overview. Publication Timeline. Most widely held works by Brigitte Jamart. Chimie organique : les cours de Paul Arnaud by Paul Arnaud 1 edition published in in French and held by 21 WorldCat member libraries worldwide.

By extrapolating an original strategy of hydrazinoacids synthesis developed in the LCPM we were able to obtain N-aminodipeptides in high optical purity in a satisfactory way.

These compounds were the indispensable precursors in order to continue the project. We were able to show that the activation of the acidic partner involved in the key reaction of Mitsunobu usually obtained by the use of the phtalimide group, could be advantageously realized by the introduction of a hydrazone moiety with strong electron-withdrawing character. An extension of this method on solid support is a result which constitutes an effective application of a Mitsunobu protocol in Solid Phase Organic Chemistry.

A preliminary study in liquid phase allowed to demonstrate that a classic peptidic coupling reaction could occur between two pseudopeptidic units. The continuation of the study was made on solid phase and allowed us to obtain the first [alpha-N-amino]peptides never synthesized to this day. Finally, in the third chapter, these oligomers were studied by molecular modelling and various spectroscopic methods NMR, IR who allowed to suggest a folding by the establishment of intramolecular hydrogen bonds.

The chemical safety of plastic materials intended to come into contact with food is strictly regulated by the European regulation No. Chemical mixtures migrating from PET into bottled water may explain the reported positive results. The aim of this study was to assess the migration of monomers, catalysts, additives, and degradation byproducts from PET into bottled water. In accordance with the chemical formulations reported for PET, no phtalates, antioxidants, and UV stabilizers were detected into bottled water.

However, formaldehyde, acetaldehyde, 2,4-di-tert-butylphenol and antimony were found in PET bottled water. It was shown that temperature influences the migration of these compounds, due to orientation loss of the amorphous phase of the semi-crystalline part of PET bottles. This phenomenon increases the mobility of polymer chains and consequently, the compounds' diffusion.

Thus, it was found that sunlight exposure influences only the migration of formaldehyde. Indeed, no oxidation of the polymer chains was detected on the surface of PET bottles after exposure. Thus foldamers can have a biological activity.

Among azapseudopeptide oligomers, substitution of a nitrogen for the CHa group is a way to preserve the side chains of analogous peptides. This substitution entails the lost of chiral center and the overall conformational and local electronic states might be affected.

The structure of the obtained oligomers was analysed by NMR and IR spectroscopies, X-ray diffraction and molecular modelling. The oligomerization of N-aminopeptids in liquid phase was achieved through an acid fluorid coupling from a building block with the protections Boc N-terminus , Bn C-terminus and phtaloyl N-side.

The second chapter presents the results obtained by different conformational spectroscopic methods NMR, IR and DC and molecular modeling on the various oligomers synthesized in Chapter 1. This work has allowed to highlight a original repetitive folding by a C8 hydrogen bond involving the carbonyl group of phthalimid and a amid proton.

Molecular dynamic calculations for oligomers based lysine residues reflected the important role of the aza-motif s in structuring the backbones regardless the chirality and nature of the amino acids.

Both molecules could organize into 3D highly ordered structures stabilized by hydrogen bonds and [pi]-stacking. Interestingly, the heterochiral cyclo- D-Phe-azaPhe-Ala 2-hexamer could form organogels. The spectroscopic and rheological studies of the organogels revealed good thermal and mechanical stability with solid-like behavior. UV and Flu studies demonstrated that the hydrogels are supported by [pi]-stacking between the aromatic groups. Both hydrogels exhibited solid-like behavior through rheological studies and the SEM analysis of the xerogels revealed fibrous structure.

This process is mediated through numerous factors including VEGF Vascular Endothelial Growth Factor which interacts with receptors overexpressed on endothelial cells of blood vessels neighboring tumor. Targeted anticancer therapies take advantage of this overexpression to design tumor-specific molecules. A new targeting agent, CBO-P11 was synthesized in the laboratory. It is a mer cyclopeptide with a high affinity for VEGF receptors. In order to increase the blood circulation time of this peptide, nanoparticles of poly vinylidene fluoride PVDF , biocompatible polymer, were used as carrier.

Different dyes were used: two fluorescent probes for optical imaging and a contrast agent for low-field magnetic resonance imaging. Each step of the nanoparticles preparation was monitored and successfully characterized by numerous techniques such as dynamic and static light scattering, small-angle neutron scattering, X-ray photoelectron spectroscopy, infrared spectroscopy, fluorescence spectroscopy and dynamic nuclear polarization.

In vitro studies were performed on endothelial cells and have shown that nanoparticles were not cytotoxic and that CBO-P11 conjugated to nanoparticles kept its specificity for VEGF receptors. Those multifunctional tools offer a great potential to target and image tumor. Consequently, the development of heat insulators has been the subject of research which has resulted in new materials: super thermal insulators with a thermal conductivity of less than 25 mW.

Despite their very weak mechanical resistance they present a fibrillar structure which gives them very interesting thermal properties. In addition, we also studied the sequential formation mechanism of these gels which resulted in a full model of their molecular organization from the single molecule to the fiber and based on a hexagonal packing symmetry. In aim of commercializing an insulator made from organic aerogels, we firstly optimized the protocol for obtaining aerogels to then work on improving their thermal and mechanical properties.

We created a new hydrophobic insulator which has both a thermal conductivity in the range of the super heat insulators' and good mechanical properties that are compatible with industrial prerequisites for the construction of buildings. Peptide coupling using AAzC revealed a tricky reactivity of this new building block, due to an easy ring-opening. We were thus able to synthesize only oligopeptides containing a single AAzC residue, blocked in the N-terminal position.

Synthesis of four dipeptides each incorporating AAzC in the N terminal position and a single stereoisomer of ACBC in the C terminal position was performed within good yields.

Cis-oligopeptides were difficult to analyze due to gelation phenomenon. The folding behaviour of these peptides was examined on the basis of IR spectroscopy, NMR studies, circular dichroism, molecular modelling studies and X-ray diffraction. We demonstrated here that AAzC has a strong preference for an 8-membered ring local structuration, and a strong tendency to induce an 8-helix in a peptide.

The first part describes the synthesis of regioselective singly-labeled nitrogen 15 hydrazide, starting from N-aminophtalimide 15N. The direct application of this first study is the synthesis of two isotopic isomers of isoniazid a front-line antituberculosis drug , which elucidate the activation of isoniazid by catalase-peroxydase from Mycobacterium tuberculosis.

Moreover the reactivity of N-acyl and N-alkyloxycarbonylaminophtalimides which can be considered as hydrazines bearing three electron-withdrawing groups including two incorporated into the phtaloyl moiety, is developed in a second part. These compounds were used in phase transfert catalysis conditions and as acidic partners in the Mitsunobu reaction for the preparation of monoalkylhydrazines, monoalkylhydrazides and alkylcarbazates.

In the third part , this current method was extented to include the preparation of protected chiral hydrazinoacid derivatives via the Mistunobu protocol.

Finally the conformationel study and reactivity of N-aminophtalimide and its derivatives is reported. The first chapter is a bibliographic study on cyclization methods of peptides and pseudopeptides backbone modified peptides and their applications.

It has been described that the incorporation of potential structural elements, like introduction of changes to peptide backbone, could be facilitating the cyclization of linear oligomers. The deprotection of phthalimid group of one of these cyclic compounds opens up new opportunities like functionalization of the deprotected nitrogen atom.

The third chapter sums up the results of the structural analyses and principally highlights the original conformations adopted by these different oligomers and the influence of the N-aminoamide bond. The structures were established through a complete study using several spectroscopic techniques NMR, IR, fluorescence, X-ray crystallography. For example, the X ray studies highlight the formation of nanotubes through an original self-assembling of deprotected cyclotetramers.

Synthesis and reactivity of 3-acetylaminothiophenes by Ahmed B. Cours de chimie organique by Paul Arnaud Book 3 editions published between and in French and held by 1 WorldCat member library worldwide Quimica orghanica geral As moleculas e as reaccoes organicas ; Quimica organica descritiva O comportamento dos compostos organicos. Audience Level. Related Identities.

Associated Subjects. Chemistry, Organic. Alternative Names. French 35 English 2. Editor , Thesis advisor , Opponent , , Author , Other , Project Page Feedback Known Problems.

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Chimie organique: exercices résolus

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Jamart, Brigitte

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