Literature DB >> 21952530

Design, synthesis and protein-targeting properties of thioether-linked hydrogen bond surrogate helices.

Andrew B Mahon1, Paramjit S Arora.   

Abstract

Appropriately-placed hydrogen bond surrogates have been demonstrated to efficiently nucleate helical conformations. Herein we describe an efficient method for the synthesis of thioether-based hydrogen bond surrogate (teHBS) helices. A teHBS helix is shown to adopt a stable conformation and target its cognate protein receptor with high affinity. This journal is © The Royal Society of Chemistry 2012

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Year:  2011        PMID： 21952530      PMCID： PMC3412876          DOI： 10.1039/c1cc14730g

Source DB:  PubMed          Journal:  Chem Commun (Camb)        ISSN： 1359-7345            Impact factor:   6.222


  32 in total

1.  Circular dichroism spectra of short, fixed-nucleus alanine helices.

Authors:  Der-Hang Chin; Robert W Woody; Carol A Rohl; Robert L Baldwin
Journal:  Proc Natl Acad Sci U S A       Date:  2002-11-11       Impact factor: 11.205

2.  Tissue sulfhydryl groups.

Authors:  G L ELLMAN
Journal:  Arch Biochem Biophys       Date:  1959-05       Impact factor: 4.013

3.  Terphenyl-based helical mimetics that disrupt the p53/HDM2 interaction.

Authors:  Hang Yin; Gui-in Lee; Hyung Soon Park; Gregory A Payne; Johanna M Rodriguez; Said M Sebti; Andrew D Hamilton
Journal:  Angew Chem Int Ed Engl       Date:  2005-04-29       Impact factor: 15.336

4.  The effect of cyclization on the enzymatic degradation of herpes simplex virus glycoprotein D derived epitope peptide.

Authors:  Regina Tugyi; Gábor Mezö; Erzsébet Fellinger; David Andreu; Ferenc Hudecz
Journal:  J Pept Sci       Date:  2005-10       Impact factor: 1.905

5.  Synthesis of constrained helical peptides by thioether ligation: application to analogs of gp41.

Authors:  Florence M Brunel; Philip E Dawson
Journal:  Chem Commun (Camb)       Date:  2005-03-11       Impact factor: 6.222

6.  Solid-phase synthesis of hydrogen-bond surrogate-derived alpha-helices.

Authors:  Gianluca Dimartino; Deyun Wang; Ross N Chapman; Paramjit S Arora
Journal:  Org Lett       Date:  2005-06-09       Impact factor: 6.005

7.  Evaluation of biologically relevant short alpha-helices stabilized by a main-chain hydrogen-bond surrogate.

Authors:  Deyun Wang; Kang Chen; John L Kulp Iii; Paramjit S Arora
Journal:  J Am Chem Soc       Date:  2006-07-19       Impact factor: 15.419

8.  Paralog-selective ligands for bcl-2 proteins.

Authors:  Anja C Gemperli; Stacey E Rutledge; Abby Maranda; Alanna Schepartz
Journal:  J Am Chem Soc       Date:  2005-02-16       Impact factor: 15.419

9.  Single turn peptide alpha helices with exceptional stability in water.

Authors:  Nicholas E Shepherd; Huy N Hoang; Giovanni Abbenante; David P Fairlie
Journal:  J Am Chem Soc       Date:  2005-03-09       Impact factor: 15.419

10.  An orthosteric inhibitor of the Ras-Sos interaction.

Authors:  Anupam Patgiri; Kamlesh K Yadav; Paramjit S Arora; Dafna Bar-Sagi
Journal:  Nat Chem Biol       Date:  2011-07-17       Impact factor: 15.040
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  9 in total

Review 1.  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

2.  Effects of side chains in helix nucleation differ from helix propagation.

Authors:  Stephen E Miller; Andrew M Watkins; Neville R Kallenbach; Paramjit S Arora
Journal:  Proc Natl Acad Sci U S A       Date:  2014-04-21       Impact factor: 11.205

3.  Reversible α-helix formation controlled by a hydrogen bond surrogate.

Authors:  Stephen E Miller; Neville R Kallenbach; Paramjit S Arora
Journal:  Tetrahedron       Date:  2011-12-29       Impact factor: 2.457

4.  Nucleation effects in peptide foldamers.

Authors:  Anupam Patgiri; Stephen T Joy; Paramjit S Arora
Journal:  J Am Chem Soc       Date:  2012-07-05       Impact factor: 15.419

Review 5.  Protein Domain Mimics as Modulators of Protein-Protein Interactions.

Authors:  Nicholas Sawyer; Andrew M Watkins; Paramjit S Arora
Journal:  Acc Chem Res       Date:  2017-05-31       Impact factor: 22.384

6.  Hydrogen Bond Surrogate Stabilization of β-Hairpins.

Authors:  Nicholas Sawyer; Paramjit S Arora
Journal:  ACS Chem Biol       Date:  2018-07-18       Impact factor: 5.100

7.  An optimal hydrogen-bond surrogate for α-helices.

Authors:  Stephen T Joy; Paramjit S Arora
Journal:  Chem Commun (Camb)       Date:  2016-04-28       Impact factor: 6.222

Review 8.  Structure-Based Design of Inhibitors of Protein-Protein Interactions: Mimicking Peptide Binding Epitopes.

Authors:  Marta Pelay-Gimeno; Adrian Glas; Oliver Koch; Tom N Grossmann
Journal:  Angew Chem Int Ed Engl       Date:  2015-06-26       Impact factor: 15.336

9.  Orthogonal functionalisation of α-helix mimetics.

Authors:  Anna Barnard; Kérya Long; David J Yeo; Jennifer A Miles; Valeria Azzarito; George M Burslem; Panchami Prabhakaran; Thomas A Edwards; Andrew J Wilson
Journal:  Org Biomol Chem       Date:  2014-09-21       Impact factor: 3.876
  9 in total

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