Literature DB >> 22642718

Microwave-enhanced solid-phase synthesis of N,N'-linked aliphatic oligoureas and related hybrids.

Céline Douat-Casassus1, Karolina Pulka, Paul Claudon, Gilles Guichard.   

Abstract

A practical and efficient microwave-assisted solid-phase method for the synthesis of N,N'-linked oligoureas and related amide/urea hybrid oligomers, featuring the use of succinimidyl (2-azido-2-substituted ethyl) carbamate monomers, is reported. The rate enhancement of urea formation under microwave irradiation combined with the mild conditions of the phosphine-based azide reduction makes this approach very effective for routine synthesis of oligoureas and possibly for library production.

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Year:  2012        PMID: 22642718     DOI: 10.1021/ol3012106

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


  5 in total

1.  Shaping quaternary assemblies of water-soluble non-peptide helical foldamers by sequence manipulation.

Authors:  Gavin W Collie; Karolina Pulka-Ziach; Caterina M Lombardo; Juliette Fremaux; Frédéric Rosu; Marion Decossas; Laura Mauran; Olivier Lambert; Valérie Gabelica; Cameron D Mackereth; Gilles Guichard
Journal:  Nat Chem       Date:  2015-09-28       Impact factor: 24.427

2.  Optimal anchoring of a foldamer inhibitor of ASF1 histone chaperone through backbone plasticity.

Authors:  Johanne Mbianda; May Bakail; Christophe André; Gwenaëlle Moal; Marie E Perrin; Guillaume Pinna; Raphaël Guerois; Francois Becher; Pierre Legrand; Seydou Traoré; Céline Douat; Gilles Guichard; Françoise Ochsenbein
Journal:  Sci Adv       Date:  2021-03-19       Impact factor: 14.136

3.  Ureidopeptide GLP-1 analogues with prolonged activity in vivo via signal bias and altered receptor trafficking.

Authors:  Juliette Fremaux; Claire Venin; Laura Mauran; Robert Zimmer; Florian Koensgen; Didier Rognan; Stavroula Bitsi; Maria A Lucey; Ben Jones; Alejandra Tomas; Gilles Guichard; Sébastien R Goudreau
Journal:  Chem Sci       Date:  2019-09-11       Impact factor: 9.825

4.  Solid-phase methodology for synthesis of O-alkylated aromatic oligoamide inhibitors of α-helix-mediated protein-protein interactions.

Authors:  Natasha S Murphy; Panchami Prabhakaran; Valeria Azzarito; Jeffrey P Plante; Michaele J Hardie; Colin A Kilner; Stuart L Warriner; Andrew J Wilson
Journal:  Chemistry       Date:  2013-03-18       Impact factor: 5.236

5.  Surfactant-facilitated crystallisation of water-soluble foldamers.

Authors:  G W Collie; K Pulka-Ziach; G Guichard
Journal:  Chem Sci       Date:  2016-02-10       Impact factor: 9.825

  5 in total

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