Relevant bibliographies by topics / Cyclopeptoids

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  1. Journal articles
  2. Dissertations / Theses
  3. Conference papers

Academic literature on the topic 'Cyclopeptoids'

Author: Grafiati
Published: 10 March 2023

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Journal articles on the topic "Cyclopeptoids"

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Sala, Giorgio Della, Brunello Nardone, Francesco De Riccardis, and Irene Izzo. "Cyclopeptoids: a novel class of phase-transfer catalysts." Org. Biomol. Chem. 11, no. 5 (2013): 726–31. http://dx.doi.org/10.1039/c2ob26764k.

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2

Comegna, Daniela, Monica Benincasa, Renato Gennaro, Irene Izzo, and Francesco De Riccardis. "Design, synthesis and antimicrobial properties of non-hemolytic cationic α-cyclopeptoids." Bioorganic & Medicinal Chemistry 18, no. 5 (March 2010): 2010–18. http://dx.doi.org/10.1016/j.bmc.2010.01.026.

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3

Schettini, Rosaria, Brunello Nardone, Francesco De Riccardis, Giorgio Della Sala, and Irene Izzo. "Cyclopeptoids as Phase-Transfer Catalysts for the Enantioselective Synthesis of α-Amino Acids." European Journal of Organic Chemistry 2014, no. 35 (November 10, 2014): 7793–97. http://dx.doi.org/10.1002/ejoc.201403224.

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4

Schettini, Rosaria, Brunello Nardone, Francesco De Riccardis, Giorgio Della Sala, and Irene Izzo. "ChemInform Abstract: Cyclopeptoids as Phase-Transfer Catalysts for the Enantioselective Synthesis of α-Amino Acids." ChemInform 46, no. 18 (April 16, 2015): no. http://dx.doi.org/10.1002/chin.201518066.

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5

Della Sala, Giorgio, Irene Izzo, Rosaria Schettini, Assunta D’Amato, and Francesco De Riccardis. "Catalytic Alkylation of 2-Aryl-2-oxazoline-4-carboxylic Acid Esters Using Cyclopeptoids; Newly Designed Phase-Transfer Catalysts." Synthesis 49, no. 06 (November 24, 2016): 1319–26. http://dx.doi.org/10.1055/s-0036-1588102.

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6

Schmidt, Ulrich. "Natürliche Cyclopeptide und Cyclopeptolide." Nachrichten aus Chemie, Technik und Laboratorium 37, no. 10 (October 1989): 1034–43. http://dx.doi.org/10.1002/nadc.19890371006.

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7

Lepage, Mathieu L., Alessandra Meli, Anne Bodlenner, Céline Tarnus, Francesco De Riccardis, Irene Izzo, and Philippe Compain. "Synthesis of the first examples of iminosugar clusters based on cyclopeptoid cores." Beilstein Journal of Organic Chemistry 10 (June 23, 2014): 1406–12. http://dx.doi.org/10.3762/bjoc.10.144.

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Cyclic N-propargyl α-peptoids of various sizes were prepared by way of macrocyclizations of linear N-substituted oligoglycines. These compounds were used as molecular platforms to synthesize a series of iminosugar clusters with different valency and alkyl spacer lengths by means of Cu(I)-catalysed azide–alkyne cycloadditions. Evaluation of these compounds as α-mannosidase inhibitors led to significant multivalent effects and further demonstrated the decisive influence of scaffold rigidity on binding affinity enhancements.
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8

Lepage, Mathieu L., Jérémy P. Schneider, Anne Bodlenner, Alessandra Meli, Francesco De Riccardis, Marjorie Schmitt, Céline Tarnus, et al. "Iminosugar-Cyclopeptoid Conjugates Raise Multivalent Effect in Glycosidase Inhibition at Unprecedented High Levels." Chemistry - A European Journal 22, no. 15 (February 24, 2016): 5151–55. http://dx.doi.org/10.1002/chem.201600338.

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9

Tedesco, Consiglia, Eleonora Macedi, Alessandra Meli, Giovanni Pierri, Giorgio Della Sala, Christina Drathen, Andrew N. Fitch, Gavin B. M. Vaughan, Irene Izzo, and Francesco De Riccardis. "Synthesis, crystallization, X-ray structural characterization and solid-state assembly of a cyclic hexapeptoid with propargyl and methoxyethyl side chains." Acta Crystallographica Section B Structural Science, Crystal Engineering and Materials 73, no. 3 (June 1, 2017): 399–412. http://dx.doi.org/10.1107/s2052520617002505.

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The synthesis and the structural characterization of a cyclic hexapeptoid with four methoxyethyl and two propargyl side chains have disclosed the presence of a hydrate crystal form [form (I)] and an anhydrous crystal form [form (II)]. The relative amounts of form (I) and form (II) in the as-purified product were determined by Rietveld refinement and depend on the purification procedures. In crystal form (I), peptoid molecules assemble in a columnar arrangement by means of side-chain-to-backbone C=CH...OC hydrogen bonds. In the anhydrous crystal form (II), cyclopeptoid molecules form ribbons by means of backbone-to-backbone CH2...OC hydrogen bonds, thus mimicking β-sheet secondary structures in proteins. In both crystal forms side chains act as joints among the columns or the ribbons and contribute to the stability of the whole solid-state assembly. Water molecules in the hydrate crystal form (I) bridge columns of cyclic peptoid molecules, providing a more efficient packing.
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Harant, Hanna, Barbara Wolff, Erwin P. Schreiner, Berndt Oberhauser, Lotte Hofer, Nicole Lettner, Sabine Maier, Jan E. de Vries, and Ivan J. Lindley. "Inhibition of Vascular Endothelial Growth Factor Cotranslational Translocation by the Cyclopeptolide CAM741." Molecular Pharmacology 71, no. 6 (March 16, 2007): 1657–65. http://dx.doi.org/10.1124/mol.107.034249.

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Dissertations / Theses on the topic "Cyclopeptoids"

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Nardone, Brunello. "Synthesis, Structure and Properties of Cyclopeptoids and Cyclopeptides." Doctoral thesis, Universita degli studi di Salerno, 2014. http://hdl.handle.net/10556/1463.

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2012 - 2013
Aim of the research project has been the synthesis of cyclopeptides and cyclopeptoids in order to investigate their structural properties and catalytic activities. In particular, studies of the arrangement and the cyclopeptoids organization in the crystal structure have been realized. Moreover, the influence of some aminoacidic residues on conformational control of peptoid skeleton was evaluated. In this context, the effect of proline, an amminoacid with an important role in the formation of secondary protein structures,1 and of a pseudo-proline residue on the cystal structure and conformational equilibria of some cyclopeptoids was evaluated. In particular, N-methoxyethyl cyclic peptoids containing proline and N-methoxyethyl hexacyclopeptoid (proline-free) in complexed and uncomplexed form (1-3, figure 1) were successfully synthesized and characterized by X-ray diffraction. In addition, the synthesis of a cyclohexapeptoid containing a pseudo-proline residue was obtained (4, figure 1). Furthermore, two isomeric amphiphilic peptoids (5 and 6, figure 1) were synthesized in order to investigate the effect of amphiphilicity on the crystal frame. All that is described in sections 2,3. Moreover, considering the well documented complexation properties of cyclopeptoids towards alkaline metals,2 the ability of some cyclohexapeptoids to work as phase-transfer catalysts was investigated in a benchmark SN2 reaction. In particular, the cyclopeptoid which revealed to be the most active was the N-[2-(2-methoxyethoxy)ethyl] side chain cyclohexapeptoid (7, figure 2). Therefore, we also tested some proline-rich cyclopeptoids in asymmetric phase transfer catalysis and the most promising demonstrated to be the cyclopeptoid 8 (figure 2) alternating N-3,5-dimethyl benzylamine glycine and proline residues. The catalytic studies mentioned are illustrated in section 4. Finally, in section 5 is reported a novel synthetic strategy for the synthesis of the biologically active cyclotide kalata B1 (9, figure 4) based on Fmoc/t-Bu solid phase synthesis and on the use of an innovative linker... [edited by author]
XII n.s.
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2

Batisse, Chloé. "Nouvelles voies de synthèse énantiosélective pour l'accès à des composés difluorométhylés." Thesis, Strasbourg, 2018. http://www.theses.fr/2018STRAF041/document.

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En dépit de sa rareté au sein des produits naturels et des processus biologiques, le fluor joue un rôle de plus en plus important dans nos vies quotidiennes. Un atome de fluor ou un groupement fluoré, lorsqu’il fait partie d’une molécule biologiquement active, permet d’améliorer drastiquement ses propriétés physiques, chimiques et biologiques. Le groupement -CHF2, en plus de posséder les propriétés remarquables communes à de nombreuses espèces émergentes fluorées, est considéré comme un bioisostère des groupements hydroxyle, thiol et amino. Il peut également être engagé dans des liaisons de type hydrogène grâce à son proton acide. Cependant, les voies de synthèse permettant d’introduire stéréosélectivement le groupe -CHF2 sont encore peu nombreuses. Par exemple, seuls peu de groupes ont concentré leurs efforts sur la synthèse d’alcools α,α-difluorométhylés. Afin de remédier à ce manque de méthodologies, deux stratégies ont été imaginées au sein de notre équipe. La première consiste à utiliser un sulfoxyde α,α-difluorométhylé énantiopur en tant qu’inducteur de chiralité. La seconde méthode repose sur l’utilisation de cyclopeptoïdes chiraux lors de la difluorométhylation énantiosélective de dérivés carbonylés dans des conditions de catalyse à transfert de phase. Ces deux stratégies ainsi que les résultats qui ont été obtenus au cours de ce projet de thèse sont exposés dans le présent manuscrit
Despite being largely absent from natural products and biological processes, fluorine plays an increasingly important role in numerous areas of our daily life. The presence of fluorine atoms or fluoroalkyl groups in bioactive molecules can indeed deeply modify their physical, chemical and biological properties. In addition to these outstanding properties common to many emerging fluorinated groups, the -CHF2 group has been shown to be an interesting bioisostere of hydroxyl, thiol and amine groups and a strong hydrogen bond donor. However, in contrast to enantioselective trifluoromethylation, the enantioselective introduction of a difluoromethyl group is still in its infancy. For instance only few examples in the literature describe the synthesis of enantioenriched α,α-difluoromethyl alcohols. As part of our study to overcome this scarcity, we envisaged two different strategies to synthesise these compounds. The first method aimed to access highly enantioenriched α,α-difluoromethyl alcohols by using an enantiopure aryl α,α-difluoromethyl sulfoxide as chiral and traceless auxiliary. Phase transfer catalysis was chosen as a second strategy for the enantioselective difluoromethylation of carbonyl derivatives in presence of chiral cyclopeptoïds. Those two methods and the results obtained are discussed in this manuscript
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3

Lepage, Mathieu. "Conception et synthèse de nouvelles classes d’iminosucres d’intérêt biologique : ingénierie click pour des systèmes multivalents." Thesis, Strasbourg, 2014. http://www.theses.fr/2014STRAF049/document.

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Des résultats récents ont montré les premières preuves d’un effet multivalent puissant des iminosucres sur l’inhibition des glycosidases, avec des gains d’affinité allant jusqu’à 10000. Afin de comprendre les différentes caractéristiques de cet « effet de cluster » et d’en poursuivre l’optimisation, de nouvelles charpentes doivent être conçues. Le premier axe de recherche a donc consisté en la mise au point d’un ensemble de techniques d’ingénierie « click » pour la synthèse de systèmes multivalents, avec le développement d’une stratégie Sweet LEGO®. Cette approche permettrait un accès simple à une grande variété de néocyclodextrines préfonctionnalisées. Le second axe a consisté en une étude de relation structure-activité autour de charpentes moléculaires polyalcynes utilisées pour préparer de nouveaux clusters par chimie « click ». Une partie des clusters a été préparée en utilisant de nouvelles charpentes cyclopeptoïdes. Ils ont permis de poursuivre l’optimisation de l’effet multivalent des iminosucres sur l’inhibition de glycosidases. En particulier, un composé portant 30 ligands a montré le meilleur effet multivalent connu sur une enzyme modèle
Recent reports have demonstrated the first pieces of evidence of a strong multivalent effect in glycosidase inhibition by iminosugars, with affinity enhancements close to 10000. In order to understand the different parameters of this “cluster effect” and to continue its optimization, new scaffolds must be designed. The first research topic was thus to develop a set of « Click » Chemistry engineering techniques for the synthesis of multivalent systems, with the development of a Sweet LEGO® strategy. In the end, it would allow an easy access to a broad range of prefunctionalized neocyclodextrins. The second research topic consisted in a structure-activity relationship study by varying the molecular polyalkyne scaffold used for the preparation of new clusters by way of « Click » Chemistry. They allowed to investigate the specific features of the iminosugar cluster effect in the inhibition of glycosidases. In particular, a compound of unprecedented valency bearing 30 iminosugar units demonstrated an unprecedented dramatic affinity enhancement for the inhibition of a model enzyme (Jack bean alpha-mannosidase)
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4

POURTIER, ALBIN. "Description et caracterisation d'agents modulant la resistance tumorale pleiotropique mediee par la p-glycoproteine." Strasbourg 1, 1993. http://www.theses.fr/1993STR15096.

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5

Schneider, Jérémy. "Synthèse d'une diversité de glycoclusters : effet multivalent sur l'inhibition des glycosidases." Thesis, Strasbourg, 2017. http://www.theses.fr/2017STRAF005.

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Les premiers iminosucres multivalents rapportés dans la littérature datent de 1999. Depuis, c’est plus d’une centaine de clusters de ce type qui ont été synthétisés et décrits une quarantaine de publications. L’obtention d’un premier effet multivalent fort sur une glycosidase, en 2010, a initié de nouveaux travaux visant à étudier et à comprendre son mécanisme et ses limites. Dans cette optique le présent travail de thèse a exploité plusieurs approches. La première partie décrit la synthèse de dendrons "cliquables" permettant de multiplier par trois ou par neuf la valence initiale des plateformes utilisées. La deuxième est une étude de la synthèse d’espaceurs rigides. La troisième est la préparation de plateformes modulables, des neo-cyclodextrines, pour obtenir un contrôle plus fin de la topologie des clusters. L’association de dendrons "cliquables" et de plateformes cyclopeptoïdes de dimensions contrôlées a abouti à un résultat sans précèdent en termes d’effet multivalent. Ainsi, le cluster 36-valent à ligands DNJ est un inhibiteur 170 000 fois plus fort que l’analogue monovalent correspondant sur l’alpha-mannosidase des pois sabre blanc (Jack Bean)
The first multivalent iminosugars were published in 1999. From this date, it’s more than a hundred of clusters that were synthesized and presented in about forty publications. In 2010, the first strong multivalent effect in glycosidase inhibition was obtained and prompted further studies of its mechanism and its limits. To reach these goals, this PhD work has developed different strategies. The first was to synthesize "clickable" dendrons which can lead to a multiplication of the initial valency of our scaffolds by three or by nine. The second approach was a study to obtain rigid linkers. The third one was the preparation of modular scaffolds, neo-cyclodextrins, in order to finely tune the topology of the resulting clusters. The combination of our "clickable" dendrons with cyclopeptoid scaffolds gave an unprecedented multivalent effect on glycosidase inhibition. The 36-valent DNJ-based cluster is indeed a 170 000-fold more potent inhibitor than the corresponding monovalent control for Jack Bean alpha-mannosidase
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Conference papers on the topic "Cyclopeptoids"

1

Oberhauser, B., B. Grohmann, and H. Sperner. "Selective Epimerisation of a Fungal Cyclopeptolide via an 2-Amino-oxazole Intermediate - Conformational Consequences." In The 2nd International Electronic Conference on Synthetic Organic Chemistry. Basel, Switzerland: MDPI, 1998. http://dx.doi.org/10.3390/ecsoc-2-01702.

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