Literature DB >> 17506576

Introduction of a triazole amino acid into a peptoid oligomer induces turn formation in aqueous solution.

Jonathan K Pokorski1, Lisa M Miller Jenkins, Hanqiao Feng, Stewart R Durell, Yawen Bai, Daniel H Appella.   

Abstract

Peptoids are a non-natural class of oligomers that are composed of repeating N-substituted glycine units and are capable of folding into helices that mimic peptide structure and function. In this letter, we report the concise synthesis of a 1,5-substituted triazole amino acid (Tzl) and its subsequent incorporation into a short peptoid. The Tzl amino acid was shown to induce turn formation in aqueous solution, thus expanding the structural repertoire available to peptoid chemists.

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Year:  2007        PMID: 17506576     DOI: 10.1021/ol070817y

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


  16 in total

1.  Construction of peptoids with all trans-amide backbones and peptoid reverse turns via the tactical incorporation of N-aryl side chains capable of hydrogen bonding.

Authors:  Joseph R Stringer; J Aaron Crapster; Ilia A Guzei; Helen E Blackwell
Journal:  J Org Chem       Date:  2010-09-17       Impact factor: 4.354

Review 2.  Sophistication of foldamer form and function in vitro and in vivo.

Authors:  Arjel D Bautista; Cody J Craig; Elizabeth A Harker; Alanna Schepartz
Journal:  Curr Opin Chem Biol       Date:  2007-11-07       Impact factor: 8.822

3.  1,4-linked 1,2,3-Triazole des-peptidic analogues of PNA (TzNA): Synthesis of TzNA oligomers by "click" reaction on solid phase and stabilization of derived triplexes with DNA.

Authors:  Gitali Devi; Krishna N Ganesh
Journal:  Artif DNA PNA XNA       Date:  2010-10

4.  Acyl hydrazides as peptoid sub-monomers.

Authors:  Bani Kanta Sarma; Muhammed Yousufuddin; Thomas Kodadek
Journal:  Chem Commun (Camb)       Date:  2011-09-05       Impact factor: 6.222

5.  Close mimicry of lung surfactant protein B by "clicked" dimers of helical, cationic peptoids.

Authors:  Michelle T Dohm; Shannon L Seurynck-Servoss; Jiwon Seo; Ronald N Zuckermann; Annelise E Barron
Journal:  Biopolymers       Date:  2009       Impact factor: 2.505

6.  Probing the bioactive conformation of an archetypal natural product HDAC inhibitor with conformationally homogeneous triazole-modified cyclic tetrapeptides.

Authors:  W Seth Horne; Christian A Olsen; John M Beierle; Ana Montero; M Reza Ghadiri
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

7.  Protein prosthesis: 1,5-disubstituted[1,2,3]triazoles as cis-peptide bond surrogates.

Authors:  Annie Tam; Ulrich Arnold; Matthew B Soellner; Ronald T Raines
Journal:  J Am Chem Soc       Date:  2007-10-03       Impact factor: 15.419

Review 8.  Structure-function relationships in peptoids: recent advances toward deciphering the structural requirements for biological function.

Authors:  Sarah A Fowler; Helen E Blackwell
Journal:  Org Biomol Chem       Date:  2009-02-11       Impact factor: 3.876

9.  Synthesis and characterization of nitroaromatic peptoids: fine tuning peptoid secondary structure through monomer position and functionality.

Authors:  Sarah A Fowler; Rinrada Luechapanichkul; Helen E Blackwell
Journal:  J Org Chem       Date:  2009-02-20       Impact factor: 4.354

10.  Submonomer synthesis of a hybrid peptoid-azapeptoid library.

Authors:  Bani Kanta Sarma; Thomas Kodadek
Journal:  ACS Comb Sci       Date:  2012-09-18       Impact factor: 3.784

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