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

• Main Authors: Maria Vittoria Spanedda, Christophe Salomé, Benoît Hilbold, Etienne Berner, Béatrice Heurtault, Sylvie Fournel, Benoît Frisch, Line Bourel-Bonnet
• Format: Article
• Language: English
• Published: Elsevier 2015-12-01
• Series: Data in Brief
• Online Access: http://www.sciencedirect.com/science/article/pii/S2352340915001705

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 DOGP3NH2 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].