Synthesis of antibacterial 1,3-diyne-linked peptoids from an Ugi-4CR/Glaser coupling approach

A library of ten 1,3-diyne-linked peptoids has been synthesized through an Ugi four-component reaction (U-4CR) followed by a copper-catalysed alkyne homocoupling (Glaser reaction). The short and chemoselective reaction sequence allows generating diverse (pseudo) dimeric peptoids. A combinatorial ver...

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Autores principales: Brauer, Martin C N, Neves Filho, Ricardo A W, Westermann, Bernhard, Heinke, Ramona, Wessjohann, Ludger A
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2015
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4311588/
https://www.ncbi.nlm.nih.gov/pubmed/25670988
http://dx.doi.org/10.3762/bjoc.11.4
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author Brauer, Martin C N
Neves Filho, Ricardo A W
Westermann, Bernhard
Heinke, Ramona
Wessjohann, Ludger A
author_facet Brauer, Martin C N
Neves Filho, Ricardo A W
Westermann, Bernhard
Heinke, Ramona
Wessjohann, Ludger A
author_sort Brauer, Martin C N
collection PubMed
description A library of ten 1,3-diyne-linked peptoids has been synthesized through an Ugi four-component reaction (U-4CR) followed by a copper-catalysed alkyne homocoupling (Glaser reaction). The short and chemoselective reaction sequence allows generating diverse (pseudo) dimeric peptoids. A combinatorial version allows the one-pot preparation of, e.g., six-compound-libraries of homo- and heterodimers verified by ESI-MS and HPLC. In a preliminary evaluation, some compounds display moderate activity against the Gram-positive bacterium Bacillus subtilis.
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spelling pubmed-43115882015-02-10 Synthesis of antibacterial 1,3-diyne-linked peptoids from an Ugi-4CR/Glaser coupling approach Brauer, Martin C N Neves Filho, Ricardo A W Westermann, Bernhard Heinke, Ramona Wessjohann, Ludger A Beilstein J Org Chem Full Research Paper A library of ten 1,3-diyne-linked peptoids has been synthesized through an Ugi four-component reaction (U-4CR) followed by a copper-catalysed alkyne homocoupling (Glaser reaction). The short and chemoselective reaction sequence allows generating diverse (pseudo) dimeric peptoids. A combinatorial version allows the one-pot preparation of, e.g., six-compound-libraries of homo- and heterodimers verified by ESI-MS and HPLC. In a preliminary evaluation, some compounds display moderate activity against the Gram-positive bacterium Bacillus subtilis. Beilstein-Institut 2015-01-07 /pmc/articles/PMC4311588/ /pubmed/25670988 http://dx.doi.org/10.3762/bjoc.11.4 Text en Copyright © 2015, Brauer et al. https://creativecommons.org/licenses/by/2.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Full Research Paper
Brauer, Martin C N
Neves Filho, Ricardo A W
Westermann, Bernhard
Heinke, Ramona
Wessjohann, Ludger A
Synthesis of antibacterial 1,3-diyne-linked peptoids from an Ugi-4CR/Glaser coupling approach
title Synthesis of antibacterial 1,3-diyne-linked peptoids from an Ugi-4CR/Glaser coupling approach
title_full Synthesis of antibacterial 1,3-diyne-linked peptoids from an Ugi-4CR/Glaser coupling approach
title_fullStr Synthesis of antibacterial 1,3-diyne-linked peptoids from an Ugi-4CR/Glaser coupling approach
title_full_unstemmed Synthesis of antibacterial 1,3-diyne-linked peptoids from an Ugi-4CR/Glaser coupling approach
title_short Synthesis of antibacterial 1,3-diyne-linked peptoids from an Ugi-4CR/Glaser coupling approach
title_sort synthesis of antibacterial 1,3-diyne-linked peptoids from an ugi-4cr/glaser coupling approach
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4311588/
https://www.ncbi.nlm.nih.gov/pubmed/25670988
http://dx.doi.org/10.3762/bjoc.11.4
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