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Smart tools and orthogonal click-like reactions onto small unilamellar vesicles: Additional molecular data

We present here the synthetic routes and the experimental data (NMR and MS spectra) for model reactions for copper-free Huisgen 1,4-cycloaddition, Staudinger ligation and for addition of a dithiol on a dibromomaleimide ring. Starting materials were synthesized from the commercially available 4-chlor...

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Autores principales: Vittoria Spanedda, Maria, Salomé, Christophe, Hilbold, Benoît, Berner, Etienne, Heurtault, Béatrice, Fournel, Sylvie, Frisch, Benoît, Bourel-Bonnet, Line
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Elsevier 2015
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4588400/
https://www.ncbi.nlm.nih.gov/pubmed/26501083
http://dx.doi.org/10.1016/j.dib.2015.08.014
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author Vittoria Spanedda, Maria
Salomé, Christophe
Hilbold, Benoît
Berner, Etienne
Heurtault, Béatrice
Fournel, Sylvie
Frisch, Benoît
Bourel-Bonnet, Line
author_facet Vittoria Spanedda, Maria
Salomé, Christophe
Hilbold, Benoît
Berner, Etienne
Heurtault, Béatrice
Fournel, Sylvie
Frisch, Benoît
Bourel-Bonnet, Line
author_sort Vittoria Spanedda, Maria
collection PubMed
description We present here the synthetic routes and the experimental data (NMR and MS spectra) for model reactions for copper-free Huisgen 1,4-cycloaddition, Staudinger ligation and for addition of a dithiol on a dibromomaleimide ring. Starting materials were synthesized from the commercially available 4-chlorophenethylamine, previously described 2-(cyclooct-2-yn-1-yloxy)acetic acid, 1-fluorocyclooct-2-ynecarboxylic acid, commercial 2-(diphenylphosphino)terephthalic acid 1-methyl 4-pentafluorophenyl diester and dibromomaleimide. In all cases, the expected compounds were obtained with good yield (50% to quantitative). A novel synthesis of the lipid anchor DOGP(3)NH(2) is also described. These data were used as basis for the study reported in the article “Smart Tools and Orthogonal Click-like Reactions onto Small Unilamellar Vesicles” in Chemistry and Physics of Lipids [1].
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spelling pubmed-45884002015-10-23 Smart tools and orthogonal click-like reactions onto small unilamellar vesicles: Additional molecular data Vittoria Spanedda, Maria Salomé, Christophe Hilbold, Benoît Berner, Etienne Heurtault, Béatrice Fournel, Sylvie Frisch, Benoît Bourel-Bonnet, Line Data Brief Data Article We present here the synthetic routes and the experimental data (NMR and MS spectra) for model reactions for copper-free Huisgen 1,4-cycloaddition, Staudinger ligation and for addition of a dithiol on a dibromomaleimide ring. Starting materials were synthesized from the commercially available 4-chlorophenethylamine, previously described 2-(cyclooct-2-yn-1-yloxy)acetic acid, 1-fluorocyclooct-2-ynecarboxylic acid, commercial 2-(diphenylphosphino)terephthalic acid 1-methyl 4-pentafluorophenyl diester and dibromomaleimide. In all cases, the expected compounds were obtained with good yield (50% to quantitative). A novel synthesis of the lipid anchor DOGP(3)NH(2) is also described. These data were used as basis for the study reported in the article “Smart Tools and Orthogonal Click-like Reactions onto Small Unilamellar Vesicles” in Chemistry and Physics of Lipids [1]. Elsevier 2015-08-28 /pmc/articles/PMC4588400/ /pubmed/26501083 http://dx.doi.org/10.1016/j.dib.2015.08.014 Text en © 2015 Published by Elsevier Inc. http://creativecommons.org/licenses/by/4.0/ This is an open access article under the CC BY license (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Data Article
Vittoria Spanedda, Maria
Salomé, Christophe
Hilbold, Benoît
Berner, Etienne
Heurtault, Béatrice
Fournel, Sylvie
Frisch, Benoît
Bourel-Bonnet, Line
Smart tools and orthogonal click-like reactions onto small unilamellar vesicles: Additional molecular data
title Smart tools and orthogonal click-like reactions onto small unilamellar vesicles: Additional molecular data
title_full Smart tools and orthogonal click-like reactions onto small unilamellar vesicles: Additional molecular data
title_fullStr Smart tools and orthogonal click-like reactions onto small unilamellar vesicles: Additional molecular data
title_full_unstemmed Smart tools and orthogonal click-like reactions onto small unilamellar vesicles: Additional molecular data
title_short Smart tools and orthogonal click-like reactions onto small unilamellar vesicles: Additional molecular data
title_sort smart tools and orthogonal click-like reactions onto small unilamellar vesicles: additional molecular data
topic Data Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4588400/
https://www.ncbi.nlm.nih.gov/pubmed/26501083
http://dx.doi.org/10.1016/j.dib.2015.08.014
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