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Literature DB >> 26400240

β-Strand mimics based on tetrahydropyridazinedione (tpd) peptide stitching.

Chang Won Kang¹, Matthew P Sarnowski¹, Sujeewa Ranatunga¹, Lukasz Wojtas¹, Rainer S Metcalf¹, Wayne C Guida¹, Juan R Del Valle¹.

Abstract

Short peptides featuring a tetrahydropyridazinedione (tpd) backbone tether exhibit reduced conformational flexibility external to the heterocyclic constraint. Analysis by NMR, molecular modeling and X-ray crystallography suggests both covalent and non-covalent stabilization of extended peptide conformations. An efficient solid-phase protocol was developed for the synthesis of a new class of β-strand mimics based on oligomeric tpd subunits.

Entities: Chemical Disease Gene Species

Mesh：

Substances：
Peptides
Pyridazines

Year: 2015 PMID： 26400240 PMCID： PMC5561724 DOI： 10.1039/c5cc07189e

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

18 in total

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2. Design of Density Functionals by Combining the Method of Constraint Satisfaction with Parametrization for Thermochemistry, Thermochemical Kinetics, and Noncovalent Interactions.

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Review 3. Beta-strand mimetics.

Authors: Wendy A Loughlin; Joel D A Tyndall; Matthew P Glenn; David P Fairlie
Journal: Chem Rev Date: 2004-12 Impact factor: 60.622

4. The chemical shift index: a fast and simple method for the assignment of protein secondary structure through NMR spectroscopy.

Authors: D S Wishart; B D Sykes; F M Richards
Journal: Biochemistry Date: 1992-02-18 Impact factor: 3.162

Review 5. Macrocycles are great cycles: applications, opportunities, and challenges of synthetic macrocycles in drug discovery.

Authors: Eric Marsault; Mark L Peterson
Journal: J Med Chem Date: 2011-03-07 Impact factor: 7.446

Review 6. The future of peptide-based drugs.

Authors: David J Craik; David P Fairlie; Spiros Liras; David Price
Journal: Chem Biol Drug Des Date: 2013-01 Impact factor: 2.817

Review 7. Constraining cyclic peptides to mimic protein structure motifs.

Authors: Timothy A Hill; Nicholas E Shepherd; Frederik Diness; David P Fairlie
Journal: Angew Chem Int Ed Engl Date: 2014-10-06 Impact factor: 15.336

Review 8. Design, synthesis, and application of azabicyclo[X.Y.0]alkanone amino acids as constrained dipeptide surrogates and peptide mimics.

Authors: Jérôme Cluzeau; William D Lubell
Journal: Biopolymers Date: 2005 Impact factor: 2.505

β-Strand mimics based on tetrahydropyridazinedione (tpd) peptide stitching.

Review 1. Macrocycles mimic the extended peptide conformation recognized by aspartic, serine, cysteine and metallo proteases.

2. Design of Density Functionals by Combining the Method of Constraint Satisfaction with Parametrization for Thermochemistry, Thermochemical Kinetics, and Noncovalent Interactions.

Review 3. Beta-strand mimetics.

4. The chemical shift index: a fast and simple method for the assignment of protein secondary structure through NMR spectroscopy.

Review 5. Macrocycles are great cycles: applications, opportunities, and challenges of synthetic macrocycles in drug discovery.

Review 6. The future of peptide-based drugs.

Review 7. Constraining cyclic peptides to mimic protein structure motifs.

Review 8. Design, synthesis, and application of azabicyclo[X.Y.0]alkanone amino acids as constrained dipeptide surrogates and peptide mimics.

9. Solid-phase synthesis of tetrahydropyridazinedione-constrained peptides.

10. Anatomy of β-strands at protein-protein interfaces.

1. Structure-Property Relationship Study of N-(Hydroxy)Peptides for the Design of Self-Assembled Parallel β-Sheets.

2. N-Amination Converts Amyloidogenic Tau Peptides into Soluble Antagonists of Cellular Seeding.

Review 3. Protein Domain Mimics as Modulators of Protein-Protein Interactions.

Review 4. Systematic Targeting of Protein-Protein Interactions.

Review 5. Heterocycles as a Peptidomimetic Scaffold: Solid-Phase Synthesis Strategies.

6. Identification of β-strand mediated protein-protein interaction inhibitors using ligand-directed fragment ligation.