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Journal articles on the topic 'Cyclopeptoids'

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Author: Grafiati

Published: 10 March 2023

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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, 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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10

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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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 (June 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 (August 18, 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 (July 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 (July 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 (August 4, 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 (January 2007): 149–57. http://dx.doi.org/10.1002/ejoc.200600354.

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17

Tedesco, Consiglia, Irene Izzo, Francesco De Riccardis, Gavin Vaughan, Michela Brunelli, Andrew Fitch, and Leonard Barboour. "Assembling nanotubes with cyclic peptoids." Acta Crystallographica Section A Foundations and Advances 70, a1 (August 5, 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 side by side arrangement of macrocycles mimicking beta-sheet secondary structure in proteins.[2] In particular, the role of side chains in the solid state assembly of peptoid macrocycles will be discussed to show how they can promote the formation of a peptoid nanotube by acting as pillars, extending vertically with respect to the macrocycle planes. [3] Examples of the solid state assembly of free and metallated cyclic peptoids will be reported to show their extreme versatility as building blocks for designing new materials, with novel chemical properties and defined biological activities. In particular the first crystal structure of a recently synthesized novel cyclic alpha-peptoid, containing open channels with a radius of approximately 7 Å, will be discussed as a case of the successful engineering of cyclopeptoid crystals. In figure it is shown the channel void surface as seen along the a axis (0.0003 au, CrystalExplorer 3.1). The results of recent variable temperature high resolution XRPD measurements performed at ESRF beamline ID31 will be also reported to highlight the unusual thermal stability of this class of compounds and how the mobility of the side chains may be exploited to prepare new functional materials. EU FP7-People- IRSES grant number 319011 is gratefully acknowledged.

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18

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 (March 17, 1993): 478–83. http://dx.doi.org/10.1093/jnci/85.6.478.

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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 (June 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 (January 1992): 11–18. http://dx.doi.org/10.1038/bjc.1992.3.

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21

Schmidt, U., A. Schumacher, J. Mittendorf, and 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, no. 2 (January 12, 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 (August 18, 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 (January 2, 1990). http://dx.doi.org/10.1002/chin.199001369.

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