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Articles de revues sur le sujet « Cyclopeptoids »

Auteur : Grafiati

Publié le 10 mars 2023

Mis à jour le 31 juillet 2025

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1

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 та Francesco De Riccardis. "Design, synthesis and antimicrobial properties of non-hemolytic cationic α-cyclopeptoids". Bioorganic & Medicinal Chemistry 18, № 5 (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 та Irene Izzo. "Cyclopeptoids as Phase-Transfer Catalysts for the Enantioselective Synthesis of α-Amino Acids". European Journal of Organic Chemistry 2014, № 35 (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 та Irene Izzo. "ChemInform Abstract: Cyclopeptoids as Phase-Transfer Catalysts for the Enantioselective Synthesis of α-Amino Acids." ChemInform 46, № 18 (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 (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 (1989): 1034–43. http://dx.doi.org/10.1002/nadc.19890371006.

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7

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

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9

Tedesco, Consiglia, Eleonora Macedi, Alessandra Meli, et al. "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 (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

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10

Harant, Hanna, Barbara Wolff, Erwin P. Schreiner, et al. "Inhibition of Vascular Endothelial Growth Factor Cotranslational Translocation by the Cyclopeptolide CAM741." Molecular Pharmacology 71, no. 6 (2007): 1657–65. http://dx.doi.org/10.1124/mol.107.034249.

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11

Emmer, Gerhard, Maximilian A. Grassberger, Josef G. Meingassner, Gerhard Schulz, and Michael Schaude. "Derivatives of a Novel Cyclopeptolide. 1. Synthesis, Antifungal Activity, and Structure-Activity Relationships." Journal of Medicinal Chemistry 37, no. 13 (1994): 1908–17. http://dx.doi.org/10.1021/jm00039a002.

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12

EMMER, G., M. A. GRASSBERGER, J. G. MEINGASSNER, G. SCHULZ, and M. SCHAUDE. "ChemInform Abstract: Derivatives of a Novel Cyclopeptolide. Part 1. Synthesis, Antifungal Activity, and Structure-Activity Relationships." ChemInform 25, no. 50 (2010): no. http://dx.doi.org/10.1002/chin.199450214.

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13

Espada, A., and M. M. Dreyfuss. "Effect of the cyclopeptolide 90-215 on the production of destruxins and helvolic acid by Metarhizium anisopliae." Journal of Industrial Microbiology and Biotechnology 19, no. 1 (1997): 7–11. http://dx.doi.org/10.1038/sj.jim.2900408.

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14

Schwabe, K., G. Steinheider, A. Lawen, R. Traber, and A. Hildebrandt. "Reversal of multidrug resistance by novel cyclosporin A analogues and the cyclopeptolide SDZ 214-103 biosynthesized in vitro." Journal of Cancer Research and Clinical Oncology 121, no. 7 (1995): 407–12. http://dx.doi.org/10.1007/bf01212947.

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15

HORNICH, E., K. THIRRING, and H. BERNER. "ChemInform Abstract: Variation of Amino Acids Within the Cyclosporin-Cyclophilin Binding Domain. Synthesis of a 21-Membered Cyclopeptolide." ChemInform 28, no. 18 (2010): no. http://dx.doi.org/10.1002/chin.199718237.

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16

Michalik, Dirk, Angela Schaks, and Ludger A. Wessjohann. "One-Step Synthesis of Natural Product-Inspired Biaryl Ether-Cyclopeptoid Macrocycles by Double Ugi Multiple-Component Reactions of Bifunctional Building Blocks." European Journal of Organic Chemistry 2007, no. 1 (2007): 149–57. http://dx.doi.org/10.1002/ejoc.200600354.

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17

Jachez, B., R. Nordmann, and F. Loor. "Restoration of Taxol Sensitivity of Multidrug-Resistant Cells by the Cyclosporine SDZ PSC 833 and the Cyclopeptolide SDZ 280-446." JNCI Journal of the National Cancer Institute 85, no. 6 (1993): 478–83. http://dx.doi.org/10.1093/jnci/85.6.478.

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18

Tedesco, Consiglia, Irene Izzo, Francesco De Riccardis, et al. "Assembling nanotubes with cyclic peptoids." Acta Crystallographica Section A Foundations and Advances 70, a1 (2014): C563. http://dx.doi.org/10.1107/s2053273314094364.

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Cyclic alpha-peptoids hold the attention of both synthetic and supramolecular chemists for their biostability and potential diversity but also for their elegant and intriguing architectures.[1] Peptoids differ from peptides in the side chains, which are shifted by one position along the peptide backbone to the nitrogen atom to give N-substituted oligoglycine. The lack of the amide proton prevents the formation of NH···OC hydrogen bonds and weaker interactions, as CH···OC hydrogen bonds and CH-pi interactions, play a key role. Inter-annular CH···OC hydrogen bonds can provide face to face or sid

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19

Emmer, Gerhard, Maximilian A. Grassberger, Gerhard Schulz, Danielle Boesch, Claire Gaveriaux, and Francis Loor. "Derivatives of a Novel Cyclopeptolide. 2. Synthesis, Activity against Multidrug Resistance in CHO and KB Cells in vitro, and Structure-Activity Relationships." Journal of Medicinal Chemistry 37, no. 13 (1994): 1918–28. http://dx.doi.org/10.1021/jm00039a003.

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20

Loor, F., D. Boesch, C. Gavériaux, B. Jachez, A. Pourtier-Manzanedo, and G. Emmer. "SDZ 280-446, a novel semi-synthetic cyclopeptolide: in vitro and in vivo circumvention of the P-glycoprotein-mediated tumour cell multidrug resistance." British Journal of Cancer 65, no. 1 (1992): 11–18. http://dx.doi.org/10.1038/bjc.1992.3.

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21

Schmidt, U., A. Schumacher, J. Mittendorf та B. Riedl. "Contribution to the synthesis of aureobasidin A. Synthesis of cyclopeptolides containing the sequence leucyl-N-methyl-β-hydroxyvalyl- (2R)-oxy-(3R)-methyl-pentanoic acid *". Journal of Peptide Research 52, № 2 (2009): 143–54. http://dx.doi.org/10.1111/j.1399-3011.1998.tb01369.x.

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22

EMMER, G., M. A. GRASSBERGER, G. SCHULZ, D. BOESCH, C. GAVERIAUX, and F. LOOR. "ChemInform Abstract: Derivatives of a Novel Cyclopeptolide. Part 2. Synthesis, Activity Against Multidrug Resistance in CHO and KB Cells in vitro, and Structure-Activity Relationships." ChemInform 25, no. 50 (2010): no. http://dx.doi.org/10.1002/chin.199450215.

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23

SCHMIDT, U. "ChemInform Abstract: Natural Cyclopeptides and Cyclopeptolides." ChemInform 21, no. 1 (1990). http://dx.doi.org/10.1002/chin.199001369.

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24

Liang, Yan, Rosaria Schettini, Nicolas Kern, et al. "Deconstructing Best‐in‐Class Neoglycoclusters as a Tool for Dissecting Key Multivalent Processes in Glycosidase Inhibition." Chemistry – A European Journal, January 15, 2024. http://dx.doi.org/10.1002/chem.202304126.

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Multivalency represents an appealing option to modulate selectivity in enzyme inhibition and transform moderate glycosidase inhibitors into highly potent ones. The rational design of multivalent inhibitors is however challenging because global affinity enhancement relies on several interconnected local mechanistic events, whose relative impact is unknown. So far, the largest multivalent effects ever reported for a non‐polymeric glycosidase inhibitor have been obtained with cyclopeptoid‐based inhibitors of Jack bean α‐mannosidase (JBα‐man). Here, we report a structure‐activity relationship (SAR

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25

Tedesco, Consiglia, Irene Izzo, Riccardis Francesco De, et al. "Assembling nanotubes with cyclic peptoids." November 9, 2015. https://doi.org/10.1107/s2053273314094364.

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Cyclic alpha-peptoids hold the attention of both synthetic and supramolecular chemists for their biostability and potential diversity but also for their elegant and intriguing architectures.[1] Peptoids differ from peptides in the side chains, which are shifted by one position along the peptide backbone to the nitrogen atom to give N-substituted oligoglycine. The lack of the amide proton prevents the formation of NH···OC hydrogen bonds and weaker interactions, as CH···OC hydrogen bonds and CH-pi interactions, play a key role. Inter-annular CH···OC hydrogen bonds can provide face to face or sid

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