European Journal of Organic Chemistry

Cover image for Vol. 2013 Issue 17

Special Issue: Foldamers

June 2013

Volume 2013, Issue 17

Pages 3408–3596

Issue edited by: Claudia Tomasini, Ivan Juc, David J. Aitken, Ferenc Fülöp

  1. Cover Picture

    1. Top of page
    2. Cover Picture
    3. Editorial
    4. Graphical Abstract
    5. News
    6. Biographies
    7. Short Communication
    8. Full Papers
    1. You have free access to this content
      Design and Synthesis of Oligoamide-Based Double α-Helix Mimetics (Eur. J. Org. Chem. 17/2013)

      Oleg V. Kulikov, Sam Thompson, Hai Xu, Christopher D. Incarvito, Richard T. W. Scott, Ishu Saraogi, Laura Nevola and Andrew D. Hamilton

      Article first published online: 6 JUN 2013 | DOI: 10.1002/ejoc.201390045

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      The cover picture shows the binding of transcription factors to nucleic acids. Top left: multicomponent protein; bottom right: leucine zipper; centre: bis-oligobenzamide peptidomimetic; background: DNA chains. The xanthene-linked bis-oligobenzamide shown in the centre is an example of a super-secondary structural protein mimic. This work details the synthesis of oligobenzamide and oligopyridylamide strands connected through various spacers, allowing tuning of the inter-helix angle and thus the potential nucleic acid or protein binding properties. Details are discussed in the article by A. D. Hamilton et al. on page 3427 ff. Dr. Karl Harrison (Department of Chemistry, University of Oxford) is gratefully acknowledged for the production of the cover picture.

  2. Editorial

    1. Top of page
    2. Cover Picture
    3. Editorial
    4. Graphical Abstract
    5. News
    6. Biographies
    7. Short Communication
    8. Full Papers
    1. Foldamers

      You have free access to this content
      Foldamers (pages 3408–3409)

      Claudia Tomasini, Ivan Huc, David J. Aitken and Ferenc Fülöp

      Article first published online: 6 JUN 2013 | DOI: 10.1002/ejoc.201300676

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      Our Guest Editors introduce this special issue on Foldamers. “This collection of publications gives a flavour of how the foldamers research area is continuously growing and expanding and we trust that it will be informative and stimulating for the organic chemistry community.”

  3. Graphical Abstract

    1. Top of page
    2. Cover Picture
    3. Editorial
    4. Graphical Abstract
    5. News
    6. Biographies
    7. Short Communication
    8. Full Papers
  4. News

    1. Top of page
    2. Cover Picture
    3. Editorial
    4. Graphical Abstract
    5. News
    6. Biographies
    7. Short Communication
    8. Full Papers
  5. Biographies

    1. Top of page
    2. Cover Picture
    3. Editorial
    4. Graphical Abstract
    5. News
    6. Biographies
    7. Short Communication
    8. Full Papers
  6. Short Communication

    1. Top of page
    2. Cover Picture
    3. Editorial
    4. Graphical Abstract
    5. News
    6. Biographies
    7. Short Communication
    8. Full Papers
    1. Transfer Hydrogenation

      A Genetically Encodable Ligand for Transfer Hydrogenation (pages 3427–3431)

      Clemens Mayer and Donald Hilvert

      Article first published online: 26 APR 2013 | DOI: 10.1002/ejoc.201300340

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      Simple tripeptides are shown to be effective ligands for iridium-catalyzed transfer hydrogenations. Peptide–iridium complexes efficiently reduce ketones, aldehydes, imines, and NAD+ under mild conditions in aqueous buffer. As genetically encodable foldamers, peptides are attractive ligands for the construction of artificial metalloenzymes for diverse biotechnological applications.

  7. Full Papers

    1. Top of page
    2. Cover Picture
    3. Editorial
    4. Graphical Abstract
    5. News
    6. Biographies
    7. Short Communication
    8. Full Papers
    1. Peptidomimetics

      Design and Synthesis of Oligoamide-Based Double α-Helix Mimetics (pages 3433–3445)

      Oleg V. Kulikov, Sam Thompson, Hai Xu, Christopher D. Incarvito, Richard T. W. Scott, Ishu Saraogi, Laura Nevola and Andrew D. Hamilton

      Article first published online: 23 MAY 2013 | DOI: 10.1002/ejoc.201300363

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      We report the modular synthesis of bis-oligobenzamides and bis-oligopyridylamides as double-helix peptidomimetics with a variety of spacers in which the disposition of strands is tuneable to mimic a range of super-secondary structures.

    2. Dinuclear Foldamers

      Dinuclear Chloride-Binding Foldamers Based on Fluorescent Oligoureas (pages 3446–3454)

      Peiju Yang, Jiamin Wang, Chuandong Jia, Xiao-Juan Yang and Biao Wu

      Article first published online: 3 APR 2013 | DOI: 10.1002/ejoc.201300043

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      A series of dinuclear chloride-binding foldamers have been synthesized from naphthyl- and anthracenyl-decorated, ortho-phenylene-bridged oligoureas (tetrakisurea to hexakisurea).

    3. Peptidomimetics

      All-Thioamidated Homo-α-Peptides: Synthesis and Conformation (pages 3455–3463)

      Fernando Formaggio, Marco Crisma, Claudio Toniolo and Cristina Peggion

      Article first published online: 27 MAR 2013 | DOI: 10.1002/ejoc.201300050

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      Short series of terminally protected, fully thioamidated, homo-α-peptides were synthesized. For the first time, their preparation was achieved in single-step fashion through direct thionation of their oxygenated precursors. Conformation analysis confirms that the thioamidated α-amino acid residues can easily adopt either folded or fully extended conformations.

    4. Foldamers

      Structural Characterization of Peptide Oligomers Containing (1R,2S)-2-Aminocyclohexanecarboxylic Acid (cis-ACHC) (pages 3464–3469)

      Soo Hyuk Choi, Monika Ivancic, Ilia A. Guzei and Samuel H. Gellman

      Article first published online: 23 APR 2013 | DOI: 10.1002/ejoc.201300118

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      Three types of peptide oligomers that contain cis-2-aminocyclohexanecarboxylic acid (cis-ACHC) were analyzed by two-dimensional NMR spectroscopy and X-ray crystallography. Folded conformations do not appear to be populated in solution. Crystallographic data reveal extended confomations with specific preferences for cis-ACHC residues.

    5. Self-Assembling Multivalency

      Self-Assembling Multivalency – Supramolecular Polymers Assembled from Monovalent Mannose-Labelled Discotic Molecules (pages 3470–3476)

      Katja Petkau-Milroy and Luc Brunsveld

      Article first published online: 4 APR 2013 | DOI: 10.1002/ejoc.201300057

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      The supramolecular multivalency of discotic molecules, which feature either a single or three mannose units and self-assemble into columnar polymers, is evaluated. The binding affinity of the multivalent supramolecular polymers is enhanced compared to that of the monovalent bioactive ligand. Additional decoration with three mannose ligands does not further contribute to the binding.

    6. Peptide Foldamer Design

      Synthesis of Cyclic γ-Amino Acids for Foldamers and Peptide Nanotubes (pages 3477–3493)

      Nuria Rodríguez-Vázquez, Stephan Salzinger, Luis F. Silva, Manuel Amorín and Juan R. Granja

      Article first published online: 13 MAR 2013 | DOI: 10.1002/ejoc.201201565

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      We describe the synthesis of cyclic γ-amino acids that have a cis relationship between the amino and the carboxylic acid groups. This makes them suitable for the design of foldamers that adopt β-sheet-type structures.

    7. Foldamers

      The Role of the Chiral cis-1,3-Disubstituted 2,2-Dimethylcyclobutane Motif in the Conformational Bias of Several Types of γ-Peptides (pages 3494–3503)

      Jordi Aguilera, Juan A. Cobos, Raquel Gutiérrez-Abad, Carles Acosta, Pau Nolis, Ona Illa and Rosa M. Ortuño

      Article first published online: 15 APR 2013 | DOI: 10.1002/ejoc.201300066

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      Extended but constrained conformations are preferred when a chiral cyclobutane moiety forms part of the backbone in different polycyclobutane γ-peptides. Nevertheless, strong hydrogen bonds promoting folded conformations are produced in hybrid peptides when the carbocycle is not part of the main polyamide skeleton but acts as a chiral branched platform providing functionalized side chains.

    8. Aromatic Oligoamide Foldamers with a “Wet Edge” as Inhibitors of the α-Helix-Mediated p53–hDM2 Protein–Protein Interaction (pages 3504–3512)

      Panchami Prabhakaran, Anna Barnard, Natasha S. Murphy, Colin A. Kilner, Thomas A. Edwards and Andrew J. Wilson

      Article first published online: 8 MAY 2013 | DOI: 10.1002/ejoc.201300069

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      A 3-O-alkylated aromatic oligoamide foldamer incorporating an additional and hydrophilic 6-O-alkyl substituent in the central monomer is shown to have improved solubility, adopt an active binding conformation and disrupt the p53–hDM2 interaction.

    9. Foldamer Aggregation Propensity

      Foldamer Stability Coupled to Aggregation Propensity of Elongated Trp-Cage Miniproteins (pages 3513–3522)

      Viktor Farkas, Barbara Csordás, Orsolya Hegyi, Gábor K. Tóth and András Perczel

      Article first published online: 25 APR 2013 | DOI: 10.1002/ejoc.201300071

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      Optical spectroscopic studies of the small, well-folded peptide foldamer, Trp-cage miniprotein. Investigation of stability-associated aggregation properties of three Trp-cage foldamers.

    10. Macrocyclic β-Sheets

      Recipe for β-Sheets: Foldamers Containing Amyloidogenic Peptide Sequences (pages 3523–3528)

      Ryan Spencer, Kevin H. Chen, Gerald Manuel and James S. Nowick

      Article first published online: 15 MAY 2013 | DOI: 10.1002/ejoc.201300221

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      Recipe for β-Sheets: Combine one N-methyl-amino acid, two δ-linked ornithine turn units, and nine α-amino acids by solid-phase peptide synthesis. Cyclize in solution, deprotect, and purify by RP-HPLC. Confirm folding by 1H NMR ROESY and magnetic anisotropy studies. Serve to laboratories interested in studying and inhibiting amyloid aggregation or studying β-sheet assembly.

    11. Peptide Structures

      The Ant-Pro Reverse-Turn Motif. Structural Features and Conformational Characteristics (pages 3529–3542)

      Vijaykumar H. Thorat, Tukaram S. Ingole, Kuruppanthara N. Vijayadas, Roshna V. Nair, Sangram S. Kale, Veera V. E. Ramesh, Hilda C. Davis, Panchami Prabhakaran, Rajesh G. Gonnade, Rupesh L. Gawade, Vedavati G. Puranik, Pattuparambil R. Rajamohanan and Gangadhar J. Sanjayan

      Article first published online: 25 APR 2013 | DOI: 10.1002/ejoc.201201739

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      Characteristic conformational features of the Ant-Pro reverse turn ― a folded pseudo β-turn motif with a closed nine-membered-ring H-bonded network involving just two amino acid residues ― are described. The results were obtained from the investigation of ten crystal structures and their NMR conformations in the solution state.

    12. Protein Folding

      Synthesis and Structural Studies of α/β-Peptides Derived from Fused Furano-pyran­ β-Amino Acid and L-Ala (pages 3543–3554)

      Gangavaram V. M. Sharma, Tailor Sridhar, Pothula Purushotham Reddy and Ajit C. Kunwar

      Article first published online: 7 MAY 2013 | DOI: 10.1002/ejoc.201300055

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      α/β-Peptides were synthesized from alternating fused furano-pyran β-amino acid/L-Ala units, and their conformations were analyzed. The system adopted a left-handed 9/11-helix that was supported by 7-mr H-bonding at the N-terminus.

    13. Foldamers

      You have full text access to this OnlineOpen article
      Foldameric β-H18/20P Mixed Helix Stabilized by Head-to-Tail Contacts: A Way to Higher-Order Structures (pages 3555–3559)

      Éva Szolnoki, Anasztázia Hetényi, István M. Mándity, Ferenc Fülöp and Tamás A. Martinek

      Article first published online: 3 APR 2013 | DOI: 10.1002/ejoc.201201633

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      The discovery of a large-diameter β-peptidic foldamer mixed helix is reported. The formation of the β-H18/20P helix is solvent- and concentration-dependent, and occurs by a head-to-tail self-assembly process in solution.

    14. Antimicrobial Peptoids

      Amphiphilic Cyclic Peptoids That Exhibit Antimicrobial Activity by Disrupting Staphylococcus aureus Membranes (pages 3560–3566)

      Mia L. Huang, Meredith A. Benson, Sung Bin Y. Shin, Victor J. Torres and Kent Kirshenbaum

      Article first published online: 19 APR 2013 | DOI: 10.1002/ejoc.201300077

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      Macrocyclic peptoid oligomers that organize into globally amphiphilic faces show potent antimicrobial activity against clinical isolates of methicillin-resistant Staphylococcus aureus (MRSA) and disrupt the bacterial cell surface, as shown by scanning electron microscopy. Scale bar: 300 nm.

    15. Foldamers

      Preorganised Dipeptide Mimics as Foldamer Building Blocks (pages 3567–3573)

      Nicola Castellucci and Claudia Tomasini

      Article first published online: 15 MAY 2013 | DOI: 10.1002/ejoc.201300194

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      Rigid, flexible, rigid: the combination of a 3,4-disubstituted oxazolidin-2-one ring, a flexible methylene group and a 1,4-disubstituted triazole ring allows the formation of a new dipeptide mimic that favours the formation of bent conformations.

    16. Aromatic Oligoamides

      Aromatic Oligoamides with a Rare ortho-Connectivity: Synthesis and Study of ortho-Arylopeptoids (pages 3574–3589)

      Thomas Hjelmgaard and John Nielsen

      Article first published online: 7 MAY 2013 | DOI: 10.1002/ejoc.201300398

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      We present the first synthesis and study of N-alkylated ortho-aminomethyl-benzamides termed “ortho-arylopeptoids”. These compounds can be synthesized both on solid-phase and in solution using a unique submonomer method and constitute a rare example of aromatic oligoamides with ortho-connectivity. The tert-butyl and phenyl side chains offer complete control over the amide conformations.

    17. Hybrid Peptide Foldamers

      C12-Helix Development in (αγ)n Sequences – Spectroscopic Characterization of Boc–[Aib–γ4(R)Val]–OMe Oligomers (pages 3590–3596)

      Bhimareddy Dinesh, Vishwanathan Vinaya, Srinivasarao Raghothama and Padmanabhan Balaram

      Article first published online: 14 MAY 2013 | DOI: 10.1002/ejoc.201300264

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      The formation of C12-helical structures in the hybrid αγ oligopeptides Boc–[Aib–γ4(R)Val]n–OMe in solution is demonstrated by NMR and IR methods. The intramolecularly hydrogen-bonded solution conformations resemble those previously determined by X-ray crystallography. C12-helix development has also been monitored by far-UV CD.

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