Literature DB >> 19343235

Structure-function relationships in peptoids: recent advances toward deciphering the structural requirements for biological function.

Sarah A Fowler1, Helen E Blackwell.   

Abstract

Oligomers of N-substituted glycine, or peptoids, are versatile tools to probe biological processes and hold promise as therapeutic agents. An underlying theme in the majority of recent peptoid research is the connection between peptoid function and peptoid structure. For certain applications, well-folded peptoids are essential for activity, while unstructured peptoids appear to suffice, or even are superior, for other applications. Currently, these structure-function connections are largely made after the design, synthesis, and characterization process. However, as guidelines for peptoid folding are elucidated and the known biological activities are expanded, we anticipate these connections will provide a pathway toward the de novo design of functional peptoids. In this perspective, we review several of the peptoid structure-function relationships that have been delineated over the past five years.

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Year:  2009        PMID: 19343235      PMCID: PMC5962266          DOI: 10.1039/b817980h

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


  75 in total

1.  Peptoid oligomers with alpha-chiral, aromatic side chains: effects of chain length on secondary structure.

Authors:  C W Wu; T J Sanborn; R N Zuckermann; A E Barron
Journal:  J Am Chem Soc       Date:  2001-04-04       Impact factor: 15.419

Review 2.  Chemical signaling among bacteria and its inhibition.

Authors:  Gholson J Lyon; Tom W Muir
Journal:  Chem Biol       Date:  2003-11

Review 3.  Quorum sensing: cell-to-cell communication in bacteria.

Authors:  Christopher M Waters; Bonnie L Bassler
Journal:  Annu Rev Cell Dev Biol       Date:  2005       Impact factor: 13.827

4.  Click to fit: versatile polyvalent display on a peptidomimetic scaffold.

Authors:  Hangjun Jang; Aaron Fafarman; Justin M Holub; Kent Kirshenbaum
Journal:  Org Lett       Date:  2005-05-12       Impact factor: 6.005

5.  Stepwise transformation of a cholera toxin and a p24 (HIV-1) epitope into D-peptide analogs.

Authors:  A Kramer; R D Stigler; T Knaute; B Hoffmann; J Schneider-Mergener
Journal:  Protein Eng       Date:  1998-10

6.  Chiral N-substituted glycines can form stable helical conformations.

Authors:  P Armand; K Kirshenbaum; A Falicov; R L Dunbrack; K A Dill; R N Zuckermann; F E Cohen
Journal:  Fold Des       Date:  1997

Review 7.  Lessons from zinc-binding peptides.

Authors:  J M Berg; H A Godwin
Journal:  Annu Rev Biophys Biomol Struct       Date:  1997

8.  Discovery of nanomolar ligands for 7-transmembrane G-protein-coupled receptors from a diverse N-(substituted)glycine peptoid library.

Authors:  R N Zuckermann; E J Martin; D C Spellmeyer; G B Stauber; K R Shoemaker; J M Kerr; G M Figliozzi; D A Goff; M A Siani; R J Simon
Journal:  J Med Chem       Date:  1994-08-19       Impact factor: 7.446

9.  Peptoids that mimic the structure, function, and mechanism of helical antimicrobial peptides.

Authors:  Nathaniel P Chongsiriwatana; James A Patch; Ann M Czyzewski; Michelle T Dohm; Andrey Ivankin; David Gidalevitz; Ronald N Zuckermann; Annelise E Barron
Journal:  Proc Natl Acad Sci U S A       Date:  2008-02-19       Impact factor: 11.205

10.  Design and synthesis of a cell-permeable synthetic transcription factor mimic.

Authors:  Xiangshu Xiao; Peng Yu; Hyun-Suk Lim; Devanjan Sikder; Thomas Kodadek
Journal:  J Comb Chem       Date:  2007-05-27
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  54 in total

1.  A chemically synthesized peptoid-based drag-tag enhances free-solution DNA sequencing by capillary electrophoresis.

Authors:  Russell D Haynes; Robert J Meagher; Annelise E Barron
Journal:  Biopolymers       Date:  2011       Impact factor: 2.505

2.  Fragmentation Patterns and Mechanisms of Singly and Doubly Protonated Peptoids Studied by Collision Induced Dissociation.

Authors:  Jianhua Ren; Yuan Tian; Ekram Hossain; Michael D Connolly
Journal:  J Am Soc Mass Spectrom       Date:  2016-02-01       Impact factor: 3.109

3.  Conformational behavior of polyalanine peptides with and without protecting groups of varying chain lengths: population of PP-II structure!

Authors:  Fateh S Nandel; Mohan L Garg; Mohd Shafique
Journal:  J Mol Model       Date:  2015-04-23       Impact factor: 1.810

4.  Hydrophobic interactions modulate antimicrobial peptoid selectivity towards anionic lipid membranes.

Authors:  Konstantin Andreev; Michael W Martynowycz; Mia L Huang; Ivan Kuzmenko; Wei Bu; Kent Kirshenbaum; David Gidalevitz
Journal:  Biochim Biophys Acta Biomembr       Date:  2018-04-03       Impact factor: 3.747

5.  Rapid photoassisted access to N,O,S-polyheterocycles with benzoazocine and hydroquinoline cores: intramolecular cycloadditions of photogenerated azaxylylenes.

Authors:  Olga A Mukhina; N N Bhuvan Kumar; Teresa M Arisco; Roman A Valiulin; Greg A Metzel; Andrei G Kutateladze
Journal:  Angew Chem Int Ed Engl       Date:  2011-08-31       Impact factor: 15.336

6.  Construction and conformational behavior of peptoids with cis-amide bond geometry: design of a peptoid with alternate φ, ψ values of inverse PP-II/PP-II and PP-I structures.

Authors:  Fateh Singh Nandel; Radhika Rani Jaswal; Avneet Saini; Vibhuti Nandel; Mohd Shafique
Journal:  J Mol Model       Date:  2014-08-31       Impact factor: 1.810

7.  Electron capture dissociation studies of the fragmentation patterns of doubly protonated and mixed protonated-sodiated peptoids.

Authors:  Bogdan Bogdanov; Xiaoning Zhao; David B Robinson; Jianhua Ren
Journal:  J Am Soc Mass Spectrom       Date:  2014-05-21       Impact factor: 3.109

8.  Synthesis and Mass Spectrometry Analysis of Oligo-peptoids.

Authors:  Jianhua Ren; Yadwinder S Mann; Yuntao Zhang; Michael D Browne
Journal:  J Vis Exp       Date:  2018-02-21       Impact factor: 1.355

9.  Novel peptoid building blocks: synthesis of functionalized aromatic helix-inducing submonomers.

Authors:  Jiwon Seo; Annelise E Barron; Ronald N Zuckermann
Journal:  Org Lett       Date:  2010-02-05       Impact factor: 6.005

10.  Synthesis of libraries of peptidomimetic compounds containing a 2-oxopiperazine unit in the main chain.

Authors:  Sujit Suwal; Thomas Kodadek
Journal:  Org Biomol Chem       Date:  2013-04-07       Impact factor: 3.876

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