Literature DB >> 20414912

Peptoid macrocycles: making the rounds with peptidomimetic oligomers.

Barney Yoo1, Sung Bin Y Shin, Mia Lace Huang, Kent Kirshenbaum.   

Abstract

Macrocyclic constraints are often employed to rigidify the conformation of flexible oligomeric systems. This approach has recently been used to organize the structure of peptoid oligomers, which are peptidomimetics composed of chemically diverse N-substituted glycine monomer units. In this review, we describe advances in the synthesis and characterization of cyclic peptoids. We evaluate how the installation of covalent constraints between the oligomer termini or side chains has been effective in defining peptoid conformations. We also discuss the potential applications for this promising family of macrocyclic peptidomimetics.

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Year:  2010        PMID: 20414912     DOI: 10.1002/chem.200903549

Source DB:  PubMed          Journal:  Chemistry        ISSN: 0947-6539            Impact factor:   5.236


  18 in total

1.  A strategy for the diversity-oriented synthesis of macrocyclic scaffolds using multidimensional coupling.

Authors:  Henning S G Beckmann; Feilin Nie; Caroline E Hagerman; Henrik Johansson; Yaw Sing Tan; David Wilcke; David R Spring
Journal:  Nat Chem       Date:  2013-08-25       Impact factor: 24.427

2.  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

Review 3.  Peptoid drug discovery and optimization via surface X-ray scattering.

Authors:  Konstantin Andreev; Michael W Martynowycz; David Gidalevitz
Journal:  Biopolymers       Date:  2019-03-20       Impact factor: 2.505

4.  Sequence-defined bioactive macrocycles via an acid-catalysed cascade reaction.

Authors:  Mintu Porel; Dana N Thornlow; Ngoc N Phan; Christopher A Alabi
Journal:  Nat Chem       Date:  2016-05-09       Impact factor: 24.427

5.  Synthesis and Characterization of Amphiphilic Cyclic Diblock Copolypeptoids from N-Heterocyclic Carbene-Mediated Zwitterionic Polymerization of N-Substituted N-carboxyanhydride.

Authors:  Chang-Uk Lee; Thomas P Smart; Li Guo; Thomas H Epps; Donghui Zhang
Journal:  Macromolecules       Date:  2011-11-29       Impact factor: 5.985

6.  Development of homomultimers and heteromultimers of lung cancer-specific peptoids.

Authors:  Jared C Hooks; Jaya P Matharage; D Gomika Udugamasooriya
Journal:  Biopolymers       Date:  2011       Impact factor: 2.505

7.  Cyclization of peptoids by formation of boronate esters.

Authors:  Sara Chirayil; Kevin J Luebke
Journal:  Tetrahedron Lett       Date:  2011-12-08       Impact factor: 2.415

8.  Androgen receptor antagonism by divalent ethisterone conjugates in castrate-resistant prostate cancer cells.

Authors:  Paul M Levine; Eugine Lee; Alex Greenfield; Richard Bonneau; Susan K Logan; Michael J Garabedian; Kent Kirshenbaum
Journal:  ACS Chem Biol       Date:  2012-08-07       Impact factor: 5.100

9.  Development of cyclic peptomer inhibitors targeting the polo-box domain of polo-like kinase 1.

Authors:  Ravichandran N Murugan; Jung-Eun Park; Dan Lim; Mija Ahn; Chaejoon Cheong; Taeho Kwon; Ky-Youb Nam; Sun Ho Choi; Bo Yeon Kim; Do-Young Yoon; Michael B Yaffe; Dae-Yeul Yu; Kyung S Lee; Jeong Kyu Bang
Journal:  Bioorg Med Chem       Date:  2013-02-27       Impact factor: 3.641

10.  De novo structure prediction and experimental characterization of folded peptoid oligomers.

Authors:  Glenn L Butterfoss; Barney Yoo; Jonathan N Jaworski; Ilya Chorny; Ken A Dill; Ronald N Zuckermann; Richard Bonneau; Kent Kirshenbaum; Vincent A Voelz
Journal:  Proc Natl Acad Sci U S A       Date:  2012-08-20       Impact factor: 11.205

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