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Literature DB >> 29897248

Mimicry of a β-Hairpin Turn by a Nonpeptidic Laterally Flexible Foldamer.

Joseph W Meisel¹, Chunhua T Hu¹, Andrew D Hamilton¹.

Abstract

The design and characterization of a proteomimetic foldamer that displays lateral flexibility endowed by intramolecular bifurcated hydrogen bonds is reported. The MAMBA scaffold, derived from meta-aminomethylbenzoic acid, adopts a serpentine conformation that mimics the side chain projection of all four residues in a β-hairpin turn.

Entities: Chemical Disease Species

Mesh：

Substances：
Peptides

Year: 2018 PMID： 29897248 PMCID： PMC6047514 DOI： 10.1021/acs.orglett.8b01463

Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.005

31 in total

Review 1. Peptidomimetics, a synthetic tool of drug discovery.

Authors: Josef Vagner; Hongchang Qu; Victor J Hruby
Journal: Curr Opin Chem Biol Date: 2008-05-14 Impact factor: 8.822

Review 2. α-Helix mimetics: outwards and upwards.

Authors: Madura K P Jayatunga; Sam Thompson; Andrew D Hamilton
Journal: Bioorg Med Chem Lett Date: 2013-12-08 Impact factor: 2.823

3. An unnatural amino acid that induces beta-sheet folding and interaction in peptides.

Authors: James S Nowick; Kit S Lam; Tatyana V Khasanova; William E Kemnitzer; Santanu Maitra; Hao T Mee; Ruiwu Liu
Journal: J Am Chem Soc Date: 2002-05-08 Impact factor: 15.419

4. Structural characterization of a beta-turn mimic within a protein-protein interface.

Authors: Björn Eckhardt; Wolfgang Grosse; Lars-Oliver Essen; Armin Geyer
Journal: Proc Natl Acad Sci U S A Date: 2010-10-11 Impact factor: 11.205

5. Luminescent pyrimidine hydrazide oligomers with peptide affinity.

Authors: Xiaoqiang Li; Stefan Miltschitzky; Burkhard König
Journal: Bioorg Med Chem Date: 2006-05-22 Impact factor: 3.641

Review 6. Protein Epitope Mimetics: From New Antibiotics to Supramolecular Synthetic Vaccines.

Authors: Katja Zerbe; Kerstin Moehle; John A Robinson
Journal: Acc Chem Res Date: 2017-06-01 Impact factor: 22.384

7. Stapled α-helical peptide drug development: a potent dual inhibitor of MDM2 and MDMX for p53-dependent cancer therapy.

Authors: Yong S Chang; Bradford Graves; Vincent Guerlavais; Christian Tovar; Kathryn Packman; Kwong-Him To; Karen A Olson; Kamala Kesavan; Pranoti Gangurde; Aditi Mukherjee; Theresa Baker; Krzysztof Darlak; Carl Elkin; Zoran Filipovic; Farooq Z Qureshi; Hongliang Cai; Pamela Berry; Eric Feyfant; Xiangguo E Shi; James Horstick; D Allen Annis; Anthony M Manning; Nader Fotouhi; Huw Nash; Lyubomir T Vassilev; Tomi K Sawyer
Journal: Proc Natl Acad Sci U S A Date: 2013-08-14 Impact factor: 11.205

Mimicry of a β-Hairpin Turn by a Nonpeptidic Laterally Flexible Foldamer.

Review 1. Peptidomimetics, a synthetic tool of drug discovery.

Review 2. α-Helix mimetics: outwards and upwards.

3. An unnatural amino acid that induces beta-sheet folding and interaction in peptides.

4. Structural characterization of a beta-turn mimic within a protein-protein interface.

5. Luminescent pyrimidine hydrazide oligomers with peptide affinity.

Review 6. Protein Epitope Mimetics: From New Antibiotics to Supramolecular Synthetic Vaccines.

7. Stapled α-helical peptide drug development: a potent dual inhibitor of MDM2 and MDMX for p53-dependent cancer therapy.

8. 2-O-alkylated para-benzamide α-helix mimetics: the role of scaffold curvature.

9. Comprehensive analysis of loops at protein-protein interfaces for macrocycle design.

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

1. Translation of Diverse Aramid- and 1,3-Dicarbonyl-peptides by Wild Type Ribosomes in Vitro.

2. Heterofunctionalized Cavitands by Macrocyclization of Sequence-Defined Foldamers.