Bibliographies thématiques / Synthetic Self-assembling Amino Acid

Littérature scientifique sur le sujet « Synthetic Self-assembling Amino Acid »

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Publié le 7 septembre 2023

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Articles de revues sur le sujet "Synthetic Self-assembling Amino Acid"

Lesiak, Marta, Aleksandra Augusciak-Duma, Anna Szydlo, Ksymena Pruszczynska et Aleksander L. Sieron. « Specific inhibition of procollagen C-endopeptidase activity by synthetic peptide with conservative sequence found in chordin. » Acta Biochimica Polonica 55, n^o 2 (7 juin 2008) : 297–305. http://dx.doi.org/10.18388/abp.2008_3076.

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Procollagen C-endopeptidase (BMP-1) and N-endopeptidase (ADAMTS-2) are key enzymes for correct and efficient conversion of fibrillar procollagens to their self assembling monomers. Thus, they have an essential role in building and controlling the quality of extracellular matrices (ECMs). Here, we tested inhibition of activity of the largest variant of BMP-1, a recombinant mammalian tolloid (mTld), in vitro by three synthetic peptides with conservative amino-acid sequences found in chordin using procollagen type I as a substrate. We also verified the specific action of best inhibitory 16 amino-acid peptide in the procollagen type I cleavage assay with the use of ADAMTS-2 (procollagen N-endopeptidase). Subsequently, we determined the critical residues and minimal sequence of six amino acids in the original 16 amino-acid peptide required to maintain the inhibitory potential. Studies on the interactions of 6 and 16 amino acid long peptides with the enzyme revealed their binding to non-catalytic, regulatory domains of mTld; the inhibitory activity was not due to the competition of peptides with the substrate for the enzyme active center, because mTld did not cleave the peptides. However, in the presence of mTld both peptides underwent cyclization by disulfide bond formation. Concluding, we have shown that procollagen C-endopeptidase may be specifically blocked via its non-catalytic domains by synthetic peptide consisting of 6 amino acids in the sequence found in highly conservative region of chordin. Thus, we hypothesize that the 6 amino-acid peptide could be a good candidate for anti-fibrotic drug development.

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Gaynanova, Gulnara, Leysan Vasileva, Ruslan Kashapov, Darya Kuznetsova, Rushana Kushnazarova, Anna Tyryshkina, Elmira Vasilieva, Konstantin Petrov, Lucia Zakharova et Oleg Sinyashin. « Self-Assembling Drug Formulations with Tunable Permeability and Biodegradability ». Molecules 26, n^o 22 (10 novembre 2021) : 6786. http://dx.doi.org/10.3390/molecules26226786.

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This review focuses on key topics in the field of drug delivery related to the design of nanocarriers answering the biomedicine criteria, including biocompatibility, biodegradability, low toxicity, and the ability to overcome biological barriers. For these reasons, much attention is paid to the amphiphile-based carriers composed of natural building blocks, lipids, and their structural analogues and synthetic surfactants that are capable of self-assembly with the formation of a variety of supramolecular aggregates. The latter are dynamic structures that can be used as nanocontainers for hydrophobic drugs to increase their solubility and bioavailability. In this section, biodegradable cationic surfactants bearing cleavable fragments are discussed, with ester- and carbamate-containing analogs, as well as amino acid derivatives received special attention. Drug delivery through the biological barriers is a challenging task, which is highlighted by the example of transdermal method of drug administration. In this paper, nonionic surfactants are primarily discussed, including their application for the fabrication of nanocarriers, their surfactant-skin interactions, the mechanisms of modulating their permeability, and the factors controlling drug encapsulation, release, and targeted delivery. Different types of nanocarriers are covered, including niosomes, transfersomes, invasomes and chitosomes, with their morphological specificity, beneficial characteristics and limitations discussed.

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Tinajero-Díaz, E., A. Martínez de Ilarduya, B. Cavanagh, A. Heise et S. Muñoz-Guerra. « Poly(amino acid)-grafted polymacrolactones. Synthesis, self-assembling and ionic coupling properties ». Reactive and Functional Polymers 143 (octobre 2019) : 104316. http://dx.doi.org/10.1016/j.reactfunctpolym.2019.104316.

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Liu, Renjie, et Gregory A. Hudalla. « Using Self-Assembling Peptides to Integrate Biomolecules into Functional Supramolecular Biomaterials ». Molecules 24, n^o 8 (12 avril 2019) : 1450. http://dx.doi.org/10.3390/molecules24081450.

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Throughout nature, self-assembly gives rise to functional supramolecular biomaterials that can perform complex tasks with extraordinary efficiency and specificity. Inspired by these examples, self-assembly is increasingly used to fabricate synthetic supramolecular biomaterials for diverse applications in biomedicine and biotechnology. Peptides are particularly attractive as building blocks for these materials because they are based on naturally derived amino acids that are biocompatible and biodegradable; they can be synthesized using scalable and cost-effective methods, and their sequence can be tailored to encode formation of diverse architectures. To endow synthetic supramolecular biomaterials with functional capabilities, it is now commonplace to conjugate self-assembling building blocks to molecules having a desired functional property, such as selective recognition of a cell surface receptor or soluble protein, antigenicity, or enzymatic activity. This review surveys recent advances in using self-assembling peptides as handles to incorporate biologically active molecules into supramolecular biomaterials. Particular emphasis is placed on examples of functional nanofibers, nanovesicles, and other nano-scale structures that are fabricated by linking self-assembling peptides to proteins and carbohydrates. Collectively, this review highlights the enormous potential of these approaches to create supramolecular biomaterials with sophisticated functional capabilities that can be finely tuned to meet the needs of downstream applications.

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Rosselin, Marie, Grégory Meyer, Pierre Guillet, Thomas Cheviet, Guillaume Walther, Annette Meister, Dimitra Hadjipavlou-Litina et Grégory Durand. « Divalent Amino-Acid-Based Amphiphilic Antioxidants : Synthesis, Self-Assembling Properties, and Biological Evaluation ». Bioconjugate Chemistry 27, n^o 3 (22 février 2016) : 772–81. http://dx.doi.org/10.1021/acs.bioconjchem.6b00002.

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Zhang, Shuguang. « Discovery and design of self-assembling peptides ». Interface Focus 7, n^o 6 (20 octobre 2017) : 20170028. http://dx.doi.org/10.1098/rsfs.2017.0028.

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Peptides are ubiquitous in nature and useful in many fields, from agriculture as pesticides, in medicine as antibacterial and antifungal drugs founded in the innate immune systems, to medicinal chemistry as hormones. However, the concept of peptides as materials was not recognized until 1990 when a self-assembling peptide as a repeating segment in a yeast protein was serendipitously discovered. Peptide materials are so called because they have bona fide materials property and are made from simple amino acids with well-ordered nanostructures under physiological conditions. These structures include well-ordered nanofibres, nanotubes and nanovesicles. These peptide materials have been used for: (i) three-dimensional tissue cell cultures of primary cells and stem cells, (ii) three-dimensional tissue printing, (iii) sustained releases of small molecules, growth factors, monoclonal antibody and siRNA, (iv) accelerated wound healing in reparative and regenerative medicine as well as tissue engineering, (v) used to stabilize membrane proteins including difficult G-protein coupled receptors and photosystem I for designing nanobiodevices, (vi) a few self-assembling peptides have been used in human clinical trials for accelerated wound healings in surgical uses and (vii) in human clinical trials for siRNA delivery for treatment of cancers. It is likely that these self-assembling peptides will open doors for more and more diverse uses. The field of self-assembling peptides is growing in a number of directions in areas of materials, synthetic biology, and clinical medicine and beyond.

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Dutta, Arpita, Suven Das, Purak Das, Suvendu Maity, Prasanta Ghosh et Soumya Shankha Biswas. « Unique supramolecular assembly of a synthetic achiral α, γ-hybrid tripeptide ». Zeitschrift für Kristallographie - Crystalline Materials 237, n^o 1-3 (1 mars 2022) : 77–81. http://dx.doi.org/10.1515/zkri-2022-0002.

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Abstract An achiral tripeptide, namely, Boc-γ-Abu-m-ABA-Aib-OMe (γ-Abu: γ−amino butyric acid; m-ABA: meta-aminobenzoic acid) was synthesized by solution phase procedure. The α, γ-hybrid peptide was designed in such a way that two dissimilar γ−amino acids, one flexible and another rigid, were positioned sidewise along with α-amino isobutyric acid (Aib) as C-terminal residue. The single crystal X-ray diffraction analysis revealed that two kinks were generated around centrally placed m-ABA. Interestingly, the peptide self-assembled via three intermolecular N–H···O and one intermolecular C–H···O hydrogen bonding interactions to supramlecular helical architecture.

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Machado, Raul, A. J. Ribeiro, J. Padrão, D. Silva, A. Nobre, J. A. Teixeira, F. J. Arias, António M. Cunha, José C. Rodríguez-Cabello et M. Casal. « Exploiting the Sequence of Naturally Occurring Elastin : Construction, Production and Characterization of a Recombinant Thermoplastic Protein-Based Polymer ». Journal of Nano Research 6 (juin 2009) : 133–45. http://dx.doi.org/10.4028/www.scientific.net/jnanor.6.133.

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Genetic engineering was used to produce an elastin-like polymer (ELP) with precise amino acid composition, sequence and length, resulting in the absolute control of MW and stereochemistry. A synthetic monomer DNA sequence encoding for (VPAVG)20, was used to build a library of concatemer genes with precise control on sequence and size. The higher molecular weight polymer with 220 repeats of VPAVG was biologically produced in Escherichia coli and purified by hot and cold centrifugation cycles, based on the reversible inverse temperature transition property of ELPs. The use of low cost carbon sources like lactose and glycerol for bacteria cells culture media was explored using Central Composite Design approach allowing optimization of fermentation conditions. Due to its self-assembling behaviour near 33 °C stable spherical microparticles with a size ~ 1µm were obtained, redissolving when a strong undercooling is achieved. The polymer produced showed hysteresis behaviour with thermal absorbing/releasing components depending on the salt concentration of the polymer solution.

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Das, Apurba K., Swarup Manna, Michael G. B. Drew, Sudip Malik, Arun K. Nandi et Arindam Banerjee. « Low Molecular Weight Organogelators from Self-assembling Synthetic Tripeptides With Coded Amino Acids : Morphological, Structural, Thermodynamic and Spectroscopic Investigations ». Supramolecular Chemistry 18, n^o 8 (1 décembre 2006) : 645–55. http://dx.doi.org/10.1080/10610270601035553.

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Varlas, Spyridon, Georgia L. Maitland et Matthew J. Derry. « Protein-, (Poly)peptide-, and Amino Acid-Based Nanostructures Prepared via Polymerization-Induced Self-Assembly ». Polymers 13, n^o 16 (5 août 2021) : 2603. http://dx.doi.org/10.3390/polym13162603.

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Proteins and peptides, built from precisely defined amino acid sequences, are an important class of biomolecules that play a vital role in most biological functions. Preparation of nanostructures through functionalization of natural, hydrophilic proteins/peptides with synthetic polymers or upon self-assembly of all-synthetic amphiphilic copolypept(o)ides and amino acid-containing polymers enables access to novel protein-mimicking biomaterials with superior physicochemical properties and immense biorelevant scope. In recent years, polymerization-induced self-assembly (PISA) has been established as an efficient and versatile alternative method to existing self-assembly procedures for the reproducible development of block copolymer nano-objects in situ at high concentrations and, thus, provides an ideal platform for engineering protein-inspired nanomaterials. In this review article, the different strategies employed for direct construction of protein-, (poly)peptide-, and amino acid-based nanostructures via PISA are described with particular focus on the characteristics of the developed block copolymer assemblies, as well as their utilization in various pharmaceutical and biomedical applications.

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Thèses sur le sujet "Synthetic Self-assembling Amino Acid"

LOCARNO, SILVIA ALICE. « UNNATURAL AMINO ACIDS AS SYNTHETIC TOOLS FOR THE PREPARATION OF COMPLEX MOLECULAR ARCHITECTURES ». Doctoral thesis, Università degli Studi di Milano, 2019. http://hdl.handle.net/2434/607175.

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Self-assembly is the process by which an organized structure spontaneously is formed from individual components, as a result of specific, local interactions between the units. In recent years, peptide-based self-assembled structures have emerged as a powerful approach for developing soft and hybrid materials due to their biocompatibility, biodegradability and easily tuning properties of the final structure. The introduction of non-natural amino acids into a peptide backbone imparts additional features such as reduced conformational flexibility, high tendency to adopt a well-defined secondary structure and enhanced metabolic stability. My PhD thesis is focused on the synthesis of ultrashort peptides containing non-natural scaffolds which are able to self-assemble and form supramolecular structures. The thesis is divided into three chapters, each one reports a project regarding the synthesis and chemical characterization of scaffolds which can be inserted in peptide sequences and exploited for developing soft or hybrid materials by self-assembly. The first chapter concerns the supramolecular assemblies of spherical shape obtained from different peptides containing Cα,α-tetrasubstituted amino acids. Firstly, the results on a pentapeptide containing norbornene amino acid is reported (work published on RSC Advances). Then, the simplification of this structure is reported until obtaining a pentapeptide containing Ala-Aib motif only. The ability of this peptide to form aggregates that can be exploited for the encapsulation of hydrophobic molecules has been studied. As a proof of concept the well-known curcumin molecule has been used. The interaction of the drug molecules with peptide aggregates has been studied using the absorption and the intrinsic fluorescence emission of curcumin. Starting from this peptide, it is also possible to develop peptide-ligands which stabilize gold nanoparticles in aqueous solution. The stability of nanoparticles has been studied using DLS and UV-vis spectroscopy. The second chapter reports on a β2,3-diarylamino acid, developed in our group, which is non-natural analogous of the dipeptide Phe-Phe. This amino acid has been used to develop hybrid antifouling film which has been characterized using different techniques (contact angles values, QCM-D). The third chapter concerns the preparation of an original heterocyclic scaffold to be inserted into a peptide backbone and its exploitation for the formation of soft materials by the way of an “induced assembly”. The electrospinning technique allowed the formation of electrospun nanofibers from these non-natural peptide-based small molecules and their characterization with several techniques (SEM, AFM, FT-IR, Raman) is reported.

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Konstantopoulos, Antonios. « Self-assembling octapeptides : effect of amino acid size and charge distribution ». Thesis, University of Manchester, 2008. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.492888.

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Self-assembling peptides are currently attracting increasing interest as biological materials with a wide range of applications, including scaffolds for tissue engineering as well as drug delivery. The objective of the current work is to study the effect of amino acid size and charge distribution on the self-assembly and gelation behaviour of a series of de novo designed octapeptides.

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Smith, Mark T. « Engineering Cell-Free Systems for Vaccine Development, Self-Assembling Nanoparticles and Codon Reassignment Applications ». BYU ScholarsArchive, 2014. https://scholarsarchive.byu.edu/etd/4449.

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This dissertation reports on the technology of cell-free protein synthesis (CFPS) including 1) stabilized lyophilized cell-free systems and 2) enhanced heterogeneous cell extracts. This work further considers applications of CFPS systems in 1) rapid vaccine development, 2) functional virus-based nanoparticles, 3) site-specific protein immobilization, and 4) expanding the language of biology using unnatural amino acids. CFPS technology is a versatile protein production platform that has many features unavailable in in vivo expression systems. The primary benefit cell-free systems provide is the direct access to the reaction environment, which is no longer hindered by the presence of a cell-wall. The “openness” of the system makes it a compelling candidate for many technologies. One limitation of CFPS is the necessity of freezing for long-term viable storage. We demonstrate that a lyophilized CFPS system is more stable against nonideal storage than traditional CFPS reagents. The Escherichia coli-based CFPS system in this work is limited by the biocatalytic machinery found natively in E. coli. To combat these limitations, exogenous biocatalysts can be expressed during fermentation of cells prepared into extract. We demonstrate that simple adjustments in the fermentation conditions can significantly increase the activity of the heterogeneous extract. Towards virus-based particles and vaccines, we demonstrate that the open nature of CFPS can be utilized for coexpression of virus proteins and self-assembly of virus particles. This technique allows for the rapid production of potential vaccines and novel functional virus-based nanoparticles. Unnatural amino acids expand the effective language of protein biology. Utilizing CFPS as an expression system, we demonstrated that the incorporation of a single specific unnatural amino acid allows for site-specific immobilization, thus stabilizing the protein against elevated temperatures and chemical denaturants. Current unnatural amino acid incorporation technologies are limited to one or few simultaneous incorporations and suffer from low efficiency. This work proposes a system that could potentially allow for upwards of 40 unnatural amino acids to be simultaneously incorporated, effectively tripling the protein code. These projects demonstrate the power and versatility of CFPS technologies while laying the foundation for promising technologies in the field of biotechnology.

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Sadowski, John Paul. « Design and synthesis of dynamically assembling DNA nanostructures ». Thesis, Harvard University, 2013. http://dissertations.umi.com/gsas.harvard:11272.

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Kinetically controlled isothermal growth is fundamental to biological development, but it remains challenging to rationally design molecular systems that self-assemble isothermally into complex geometries via prescribed assembly and disassembly pathways. By exploiting the programmable chemistry of base pairing, sophisticated spatial and temporal control have both been demonstrated in DNA self-assembly, but largely as separate pursuits. This dissertation extends a new approach, called developmental self-assembly, that integrates temporal with spatial control by using a prescriptive molecular program to specify the kinetic pathways by which DNA molecules isothermally self-assemble into well-defined three-dimensional geometries.
Chemistry and Chemical Biology

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Ménard, Nathalie. « Tensioactifs d’origine naturelle pour la solubilisation de principes actifs : synthèse, physico-chimie et toxicité ». Thesis, Paris 11, 2011. http://www.theses.fr/2011PA114832/document.

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L’objectif de ce travail de thèse est de développer de nouveaux agents tensioactifs, capables de s’auto-assembler sous forme de micelles permettant de solubiliser les principes actifs insolubles, en vue de leur administration par voie intraveineuse. Cette étude a permis la synthèse, la caractérisation physico-chimique ainsi que l’évaluation toxicologique in vitro et in vivo de nouveaux agents tensioactifs d’origine naturelle. Au cours de cette étude, différentes familles de tensioactifs ont été évaluées. Ces nouveaux agents tensioactifs sont composés d’une partie hydrophobe de type cholestérol, sels biliaires ou lipides, associée via une fonction amide à une partie hydrophile dérivée d’acides aminés tels que la lysine, la glutamine ou l’acide glutamique.Ces travaux expérimentaux ont permis d’étudier l’influence de la flexibilité de la partie hydrophobe sur la capacité de solubilisation des tensioactifs. Cette étude a montré que l’efficacité de solubilisation est reliée à la flexibilité de la partie hydrophobe. L’utilisation d’agents tensioactifs composés d’une chaîne lipidique saturée flexible a permis de solubiliser efficacement le principe actif insoluble avec un taux de charge de 46 % (m/m). Les tensioactifs composés de lipides saturés sont donc plus efficaces en termes de solubilisation que les dérivés de stéroïdes ou de lipides polyinsaturés, moins flexibles. Les études de toxicité ont mis en évidence la relation ente la structure chimique des tensioactifs et leur toxicité, en particulier vis-à-vis des membranes cellulaires. L’introduction de doubles liaisons en configuration cis dans la partie lipidique des tensioactifs permet de diminuer leur interaction avec les membranes cellulaires et donc leur toxicité mais diminue également leur capacité de solubilisation. Le développement de nouveaux agents tensioactifs nécessite donc de trouver un compromis entre la capacité de solubilisation et la toxicité des tensioactifs
The aim of this thesis was to develop novel surfactants, able to self-assemble into micelles and to solubilize insoluble drugs intented for intravenous injection. Natural-based surfactants were synthesized and their physico-chemical properties were evaluated. In addition, their in vitro and in vivo toxicity were evaluated. Their drug solubilization abitity was also investigated. Three surfactant classes were evaluated. They were composed of a hydrophobic moiety, such as cholesterol, bile salts or lipids, bonded to a hydrophilic moiety, deriving from amino acids, such as lysine, glutamine or glutamic acid, via an amide bond.The influence of surfactant hydrophobic moiety flexibility on drug solubilization ability was evaluated. This study evidenced that solubilization efficiency is related to the surfactant hydrophobic moiety flexibility. The use of surfactants with flexible and saturated lipidic moieties increased drug water solubility with a drug loading of 46 % (w/w). Saturated lipid-based surfactants exhibited a better solubilization efficiency, in comparison with steroid-based surfactants or poly-unsaturated-based surfactants. Toxicity studies evidenced the relation between surfactant chemical structure and their toxicity, in particular with cell membranes. The introduction of double bond in cis configuration in surfactant lipidic moiety decreased their interaction with cell membranes and thus their toxicity. In addition, this chemical modification also decreased their solubilization ability. To develop novel surfactants, it is thus necessary to take into account drug solubilization ability and toxicity of surfactants

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Awada, Hawraà. « Synthèse sélective de γ-amino acides cyclobutaniques : préparation de nouveaux organogélateurs peptidiques ». Thesis, Paris 11, 2014. http://www.theses.fr/2014PA112365/document.

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L’acide γ-aminobutyrique ou GABA est le principal neurotransmetteur inhibiteur présent dans le système nerveux central (CNS). Afin d’obtenir un nouveau dérivé cyclobutanique du GABA, le cis-3,4CB-GABA, sous forme énantiomériquement pure, deux stratégies de synthèses efficaces et reproductibles ont été mises au point. Ces deux voies de synthèse impliquent toutes les deux une étape-clé de photocycloaddition [2+2] qui permet de créer le cycle à 4 chaînons. La première consiste en une homologation de l’acide cis-2-aminocyclobutanique (cis-ACBC), et la deuxième est une synthèse multi-étape qui utilise le caprolactame comme composé de départ.D’autre part, grâce à une synthèse stéréosélective du (1R,2S)-cis-2,3CB-GABA, quelques oligomères C- et N-protégés – di, tri, et tétra-peptides – de cet aminoacide ont été préparés. Ceux-ci ont été caractérisés par les techniques de RMN 1D et 2D, IR, RX. Les analyses ont montré qu’il n’existe pas d’interactions non-covalentes (liaisons hydrogène) inter-résidu au sein de ces structures moléculaires. En revanche, la propriété de gélification de ces oligomères dans différents solvants organiques a été mise en évidence. Des solutions et des gels formés à partir de ces peptides ont été analysés par microscope électronique à balayage et des clichés ont été obtenus montrant une organisation du dipeptide et du tetrapeptide en fibrilles. Le tripeptide lui n’a présenté aucun assemblage intermoléculaire régulier
The γ-aminobutyric acid (GABA) is the major inhibitory neurotransmitter in the central nervous system (CNS). In order to obtain new enantiomerically pure cyclobutanic derivative of GABA, the cis-3,4CB-GABA, two efficient synthetic strategies have been established. Both synthetic routes employed a photocycloaddition [2 +2] protocol, which provided the cyclobutanic ring. The first route involved the homolgation of the cis-2-aminocyclobutanecarboxylic acid (cis-ACBC), whereas the second route is a multi-step synthesis using caprolactam as starting material.On the other hand, the (1R,2S)-cis-GABA-2,3CB was synthetized, and a series of N- and C-protected oligomers of di, tri, and tetrapeptides of this amino acid were prepared. These oligomers were characterized by NMR (1D and 2D) techniques, IR, and X-ray. The analyses have shown that there are no non-covalent interactions (hydrogen bonds) between the residues of each oligomers. However, the gelation property of these oligomers in various organic solvents was demonstrated. Solutions and gels formed from these peptides were analyzed by scanning electron microscopy, and the obtained images showed a fibrous organization of the di- and tetrapeptide, while the tripeptide showed no regular intermolecular assembly

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Rapisarda, Alessandro. « Novel self-assembled monolayer (SAM) based on calix[n]arenes for application as chemical sensors and optical devices : synthesis, studies and applications ». Doctoral thesis, Università di Catania, 2013. http://hdl.handle.net/10761/1281.

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The vast majority of chemical sensors contain a chemically sensitive layer for analytes detection coupled with a transducer which transforms this interaction in a readable signal. It is well-known that calixarenes are used for the molecular recognition of ions, amino acids, hormones, sugars, peptides, nucleic acids, and proteins, which are fundamental substrates in biological and artificial processes. We developed new calix[n]arene based systems that are not only stable but are also capable of molecular recognition towards amino acids once assembled on the gold surface. By suitable modification, the system could become a potential receptor for biologically important amines and proteins.

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Hu, Xiaobo. « Synthèse, analyses structurales et assemblage de foldamères oligoamide hydrosolubles à base de quinolines ». Thesis, Bordeaux, 2017. http://www.theses.fr/2017BORD0611/document.

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La chimie des foldamères est un domaine de recherche en pleine expansion où les chimistes explorent la construction d’architectures artificielles variées mimant les structures repliées des biopolymères naturels. Les foldamères d’oligoamides quinoline, constituent une branche importante des foldamères montrant de nombreuses caractéristiques attractives, incluant la stabilité et la prédictibilité de leurs conformations repliées, qui en font de bons candidats pour des applications biologiques. Jusqu’à présent, la plupart des études sur les foldamères d’oligoamides quinolines ont été menées dans des solvants organiques. Cette thèse a pour objectif d’étendre leur portée au milieu aqueux et présente plusieurs méthodologies pour parvenir à leur solubilité, leur repliement, la variation de leurs chaines latérales, leur agrégation et leur capacité à former des cristaux dans l’eau.Tout d’abord, une méthode de synthèse en phase solide a été développée permettant l’accès rapide aux foldamères hybrides α-amino acide/quinoline (X/Q). Leur étude dans l’eau montre que contrairement aux foldamères hybrides de type (XQ)n, ceux de type (XQ2)n sont capables d’adopter une conformation hélicoïdale présentant un alignement des chaines α-amino acides dans l’espace. Ensuite, plusieurs chaines latérales courtes ont été identifiées pour doter les foldamères aromatiques d’une solubilité et d’une capacité à cristalliser dans l’eau. Six oligoamides quinoline ont ainsi été synthétisés pour une étude modèle. Des cristaux ont été obtenus pour toutes les séquences sauf une, présentant une excessive solubilité dans l’eau. Enfin, des efforts ont été faits pour construire des faisceaux d’hélices auto-assemblés dans l’eau à base d’effets hydrophobes et d’interactions électrostatiques. Les études RMN et cristallographiques ont indiqué que les effets hydrophobes étaient plus faibles qu’attendu et ne provoquaient pas d’agrégation forte
Foldamer chemistry is a rapidly expanding research field where chemists explore the construction of various artificial architectures that mimic the folded structures of biopolymers found in nature. Quinoline oligoamide foldamers, as an important branch of foldamers, have been shown to possess many desirable features, including stability and predictability of their folded conformations, and are promising candidates to achieve biological applications. Up to now, most investigations of quinoline oligoamide foldamers have been carried out in organic solvents. This thesis is aimed to expand their scope in aqueous medium and presents several methodologies to achieve solubility, folding, side-chain variation, aggregation and crystal growth ability in water.First, a solid phase synthesis method was developed to enable the fast access to α-amino acid/quinoline (X/Q) hybrid oligoamide foldamers. The study of these hybrid foldamers in water showed that contrary to (XQ)n-type foldamers the (XQ2)n-type foldamers could adopt aromatic helical conformations with α-amino acid side chains aligned in space. Then, several short side chains were identified to endow aromatic foldamers with both solubility in, and crystal growth ability from water. Six quinoline oligoamides displaying these side chains were synthesized as a case study. Crystals were obtained from aqueous medium in all cases but one, exceedingly soluble in water. At last, efforts were made to construct self-assembled aromatic helix bundles in water based on hydrophobic effects and electrostatic interactions. NMR and crystallographic studies indicated that hydrophobic effects are weaker than expected and not strongly conducive of aggregation

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Rost, Ulrike. « Organisation and Recognition of Artificial Transmembrane Peptides ». Doctoral thesis, Niedersächsische Staats- und Universitätsbibliothek Göttingen, 2016. http://hdl.handle.net/11858/00-1735-0000-002B-7CA6-D.

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« A library of natural alpha-amino acid-based dendrons synthesis, characterization and self-assembling properties ». 2003. http://library.cuhk.edu.hk/record=b6073532.

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"March 2003."
Thesis (Ph.D.)--Chinese University of Hong Kong, 2003.
Includes bibliographical references (p. 116-126).
Electronic reproduction. Hong Kong : Chinese University of Hong Kong, [2012] System requirements: Adobe Acrobat Reader. Available via World Wide Web.
Mode of access: World Wide Web.
Abstracts in English and Chinese.

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Chapitres de livres sur le sujet "Synthetic Self-assembling Amino Acid"

Tang, Ben Zhong, Kevin K. L. Cheuk, Fouad Salhi, Bingshi Li, Jacky W. Y. Lam, John A. K. Cha et Xudong Xiao. « Synthesis, Helical Chirality, and Self-Assembling Hierarchical Structures of Amino Acid-Containing Polyacetylenes ». Dans ACS Symposium Series, 133–48. Washington, DC : American Chemical Society, 2002. http://dx.doi.org/10.1021/bk-2002-0812.ch010.

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Haspel, Nurit, Jie Zheng, Carlos Aleman, David Zanuy et Ruth Nussinov. « A Protocol for the Design of Protein and Peptide Nanostructure Self-Assemblies Exploiting Synthetic Amino Acids ». Dans Methods in Molecular Biology, 323–52. New York, NY : Springer New York, 2016. http://dx.doi.org/10.1007/978-1-4939-6637-0_17.

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Meldal, Morten, et Robert C. Sheppard. « ESTERS OF FMOC-AMINO ACIDS WITH 3,4,-DIHYDRO-3-HYDROXY-4-OXO-1,2,3-BENZOTRIAZINE. A NEW CLASS OF SELF-INDICATING, ACTIVATED INTERMEDIATES FOR SOLID PHASE SYNTHESIS ». Dans Porto Carras, Chalkidiki, Greece, Aug. 31–Sept. 5, 1986, sous la direction de Dimitrios Theodoropoulos, 131–34. Berlin, Boston : De Gruyter, 1987. http://dx.doi.org/10.1515/9783110864243-027.

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Chhabra, Seema, Smrity Sahu, Keshav Sharma, Maryada Sharma, Lekha Rani, Ranjana Minz et Sunil Dogra. « Th17/IL-17, Immunometabolism and Psoriatic Disease : A Pathological Trifecta ». Dans Psoriasis [Working Title]. IntechOpen, 2022. http://dx.doi.org/10.5772/intechopen.102633.

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The burgeoning arena of immunometabolism provides evidence of how cellular, as well as local (tissue)/systemic metabolic pathways, are playing an important role in controlling immunity and inflammation. An intricate and elaborate network of various metabolic circuits specifically glycolysis, fatty acid oxidation and synthesis and amino acid metabolism precisely generate metabolites that rewire the immune response. Psoriasis is a chronic progressive self-perpetuated “IL-17-centric” inflammatory disease characterized by the co-existence of autoimmune and autoinflammatory pathways. Metabolic responses, governed by oxygen levels, nutrient availability, growth factors, cytokines, AMP/ATP ratios and amino acids, play a pivotal role in programming Th17 cell fate determination. Understanding the intricate interactions and complex interplay of molecular mechanisms responsible for Th17 cell metabolic rewiring, an important determinant of Th17 cell plasticity and heterogeneity, holds the potential to reshape psoriatic therapeutics in ways currently unimagined. This chapter entails with most recent updates on major cellular and systemic metabolic pathways regulating differentiation of Th17 cells as well their cross-talk with intracellular signaling mediators and also sheds light on how dysregulation of these pathways can be responsible for immune impairment and development of psoriatic disease. A better understanding of these metabolic processes could unveil an intriguing leverage point for therapeutic interventions to modulate metabolic programming and Th17 cell responses in this multi-systemic inflammatory disease.

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Actes de conférences sur le sujet "Synthetic Self-assembling Amino Acid"

Han, Sang-Cheol, Kwang-Min Choi et Sang-Eon Park. « Facile Synthesis of Mesoporous Silica Nanotubes With Amide Type Surfactant ». Dans ASME 2008 2nd Multifunctional Nanocomposites and Nanomaterials International Conference. ASMEDC, 2008. http://dx.doi.org/10.1115/mn2008-47070.

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Novel synthetic method for the formation of mesoporous silica nanotubes was proposed using glycyldodecylamide (GDA) as an amino acid surfactant, which enabled to control the tube diameter, wall structure and morphology with the diverse structures of amphiphile due to the capability of H-bonds by forming amide bond. Moreover, this sol-gel transcription process could be elucidated at neutral condition that enabled the recyclable use of surfactant and resulted in unique structures depending on the temperatures of self-assembly.

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