Literature DB >> 18075658

Synthesis of functionalised aromatic oligamide rods.

Jeffrey Plante1, Fred Campbell, Barbora Malkova, Colin Kilner, Stuart L Warriner, Andrew J Wilson.   

Abstract

A current goal in synthetic chemistry is the design and synthesis of molecules that adopt well defined conformations-so called foldamers. In this manuscript we describe a modular approach for construction of rod shaped para-oligobenzamide molecules. Our approach permits regiospecific incorporation of side chains through a phenolic ether linkage on the scaffold; a feature that partly restricts the conformation of the rod through intramolecular hydrogen-bonding.

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Year:  2007        PMID: 18075658      PMCID: PMC2679363          DOI: 10.1039/b712606a

Source DB:  PubMed          Journal:  Org Biomol Chem        ISSN: 1477-0520            Impact factor:   3.876


  20 in total

1.  Design and application of an alpha-helix-mimetic scaffold based on an oligoamide-foldamer strategy: antagonism of the Bak BH3/Bcl-xL complex.

Authors:  Justin T Ernst; Jorge Becerril; Hyung Soon Park; Hang Yin; Andrew D Hamilton
Journal:  Angew Chem Int Ed Engl       Date:  2003-02-03       Impact factor: 15.336

2.  beta-Peptides as inhibitors of protein-protein interactions.

Authors:  Joshua A Kritzer; Olen M Stephens; Danielle A Guarracino; Samuel K Reznik; Alanna Schepartz
Journal:  Bioorg Med Chem       Date:  2005-01-03       Impact factor: 3.641

3.  Toward beta-amino acid proteins: a cooperatively folded beta-peptide quaternary structure.

Authors:  Jade X Qiu; E James Petersson; Erin E Matthews; Alanna Schepartz
Journal:  J Am Chem Soc       Date:  2006-09-06       Impact factor: 15.419

Review 4.  Foldamers as versatile frameworks for the design and evolution of function.

Authors:  Catherine M Goodman; Sungwook Choi; Scott Shandler; William F DeGrado
Journal:  Nat Chem Biol       Date:  2007-05       Impact factor: 15.040

5.  Helix bundle quaternary structure from alpha/beta-peptide foldamers.

Authors:  W Seth Horne; Joshua L Price; James L Keck; Samuel H Gellman
Journal:  J Am Chem Soc       Date:  2007-03-16       Impact factor: 15.419

Review 6.  Shape-persistent aromatic amide oligomers: new tools for supramolecular chemistry.

Authors:  Zhan-Ting Li; Jun-Li Hou; Chuang Li; Hui-Ping Yi
Journal:  Chem Asian J       Date:  2006-12-18

Review 7.  Crescent oligoamides: from acyclic "macrocycles" to folding nanotubes.

Authors:  B Gong
Journal:  Chemistry       Date:  2001-10-15       Impact factor: 5.236

8.  Helical structures of N-alkylated poly(p-benzamide)s.

Authors:  Aya Tanatani; Akihiro Yokoyama; Isao Azumaya; Yoshinori Takakura; Chikashi Mitsui; Motoo Shiro; Masanobu Uchiyama; Atsuya Muranaka; Nagao Kobayashi; Tsutomu Yokozawa
Journal:  J Am Chem Soc       Date:  2005-06-15       Impact factor: 15.419

9.  Hydrogen bond-induced rigid oligoanthranilamide ribbons that are planar and straight.

Authors:  Zong-Quan Wu; Xi-Kui Jiang; Shi-Zheng Zhu; Zhan-Ting Li
Journal:  Org Lett       Date:  2004-01-22       Impact factor: 6.005

10.  Hydrogen bonded oligohydrazide foldamers and their recognition for saccharides.

Authors:  Jun-Li Hou; Xue-Bin Shao; Guang-Ju Chen; Yan-Xia Zhou; Xi-Kui Jiang; Zhan-Ting Li
Journal:  J Am Chem Soc       Date:  2004-10-06       Impact factor: 15.419

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  14 in total

1.  Evaluating minimalist mimics by exploring key orientations on secondary structures (EKOS).

Authors:  Dongyue Xin; Eunhwa Ko; Lisa M Perez; Thomas R Ioerger; Kevin Burgess
Journal:  Org Biomol Chem       Date:  2013-10-14       Impact factor: 3.876

2.  Synthetic alpha-helix mimetics as agonists and antagonists of islet amyloid polypeptide aggregation.

Authors:  Ishu Saraogi; James A Hebda; Jorge Becerril; Lara A Estroff; Andrew D Miranker; Andrew D Hamilton
Journal:  Angew Chem Int Ed Engl       Date:  2010       Impact factor: 15.336

Review 3.  Inhibition of α-helix-mediated protein-protein interactions using designed molecules.

Authors:  Valeria Azzarito; Kérya Long; Natasha S Murphy; Andrew J Wilson
Journal:  Nat Chem       Date:  2013-03       Impact factor: 24.427

4.  Design, synthesis, and validation of a β-turn mimetic library targeting protein-protein and peptide-receptor interactions.

Authors:  Landon R Whitby; Yoshio Ando; Vincent Setola; Peter K Vogt; Bryan L Roth; Dale L Boger
Journal:  J Am Chem Soc       Date:  2011-06-15       Impact factor: 15.419

5.  Perturbation of the c-Myc-Max protein-protein interaction via synthetic α-helix mimetics.

Authors:  Kwan-Young Jung; Huabo Wang; Peter Teriete; Jeremy L Yap; Lijia Chen; Maryanna E Lanning; Angela Hu; Lester J Lambert; Toril Holien; Anders Sundan; Nicholas D P Cosford; Edward V Prochownik; Steven Fletcher
Journal:  J Med Chem       Date:  2015-03-30       Impact factor: 7.446

6.  Targeting the Side-Chain Convergence of Hydrophobic α-Helical Hot Spots To Design Small-Molecule Mimetics: Key Binding Features for i, i + 3, and i + 7.

Authors:  Zhen Wang; Haitao Ji
Journal:  J Med Chem       Date:  2019-10-22       Impact factor: 7.446

7.  Oligobenzamide proteomimetic inhibitors of the p53-hDM2 protein-protein interaction.

Authors:  Jeffrey P Plante; Thomas Burnley; Barbora Malkova; Michael E Webb; Stuart L Warriner; Thomas A Edwards; Andrew J Wilson
Journal:  Chem Commun (Camb)       Date:  2009-06-24       Impact factor: 6.222

8.  Towards vast libraries of scaffold-diverse, conformationally constrained oligomers.

Authors:  Thomas Kodadek; Patrick J McEnaney
Journal:  Chem Commun (Camb)       Date:  2016-03-21       Impact factor: 6.222

9.  Modeling of arylamide helix mimetics in the p53 peptide binding site of hDM2 suggests parallel and anti-parallel conformations are both stable.

Authors:  Jonathan C Fuller; Richard M Jackson; Thomas A Edwards; Andrew J Wilson; Michael R Shirts
Journal:  PLoS One       Date:  2012-08-20       Impact factor: 3.240

10.  New N-phenylpyrrolamide DNA gyrase B inhibitors: Optimization of efficacy and antibacterial activity.

Authors:  Martina Durcik; Denise Lovison; Žiga Skok; Cristina Durante Cruz; Päivi Tammela; Tihomir Tomašič; Davide Benedetto Tiz; Gábor Draskovits; Ákos Nyerges; Csaba Pál; Janez Ilaš; Lucija Peterlin Mašič; Danijel Kikelj; Nace Zidar
Journal:  Eur J Med Chem       Date:  2018-05-10       Impact factor: 6.514

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