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-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].
Laboratoire de Conception et Application de Molécules Bioactives, Equipe de BioVectorologie, UMR 7199 - CNRS/Université de Strasbourg, Faculté de Pharmacie, 74 route du Rhin, BP 60024, 67401 Illkirch Cedex, France.
Maria
M
Vittoria Spanedda
Laboratoire de Conception et Application de Molécules Bioactives, Equipe de BioVectorologie, UMR 7199 - CNRS/Université de Strasbourg, Faculté de Pharmacie, 74 route du Rhin, BP 60024, 67401 Illkirch Cedex, France.
Christophe
C
Salomé
Laboratoire de Conception et Application de Molécules Bioactives, Equipe de BioVectorologie, UMR 7199 - CNRS/Université de Strasbourg, Faculté de Pharmacie, 74 route du Rhin, BP 60024, 67401 Illkirch Cedex, France.
Benoît
B
Hilbold
Laboratoire de Conception et Application de Molécules Bioactives, Equipe de BioVectorologie, UMR 7199 - CNRS/Université de Strasbourg, Faculté de Pharmacie, 74 route du Rhin, BP 60024, 67401 Illkirch Cedex, France.
Etienne
E
Berner
Laboratoire de Conception et Application de Molécules Bioactives, Equipe de BioVectorologie, UMR 7199 - CNRS/Université de Strasbourg, Faculté de Pharmacie, 74 route du Rhin, BP 60024, 67401 Illkirch Cedex, France.
Béatrice
B
Heurtault
Laboratoire de Conception et Application de Molécules Bioactives, Equipe de BioVectorologie, UMR 7199 - CNRS/Université de Strasbourg, Faculté de Pharmacie, 74 route du Rhin, BP 60024, 67401 Illkirch Cedex, France.
Sylvie
S
Fournel
Laboratoire de Conception et Application de Molécules Bioactives, Equipe de BioVectorologie, UMR 7199 - CNRS/Université de Strasbourg, Faculté de Pharmacie, 74 route du Rhin, BP 60024, 67401 Illkirch Cedex, France.
Benoît
B
Frisch
Laboratoire de Conception et Application de Molécules Bioactives, Equipe de BioVectorologie, UMR 7199 - CNRS/Université de Strasbourg, Faculté de Pharmacie, 74 route du Rhin, BP 60024, 67401 Illkirch Cedex, France.
Line
L
Bourel-Bonnet