title: Functionalization of fatty acid vesicles through newly synthesized bolaamphiphile-DNA conjugates.
abstract: The surface functionalization of fatty acid vesicles will allow their use as nanoreactors for complex chemistry. In this report, the tethering of several DNA conjugates to decanoic acid vesicles for molecular recognition and synthetic purposes was explored. Due to the highly dynamic nature of these structures, only one novel bola-amphiphile DNA conjugate could interact efficiently with or spontaneously pierce into the vesicle bilayers without jeopardizing their self-assembly or stability. This molecule was synthesized via a Cu(I)-catalyzed [3 + 2] azide-alkyne cycloaddition (click reaction), and consists of a single hydrocarbon chain of 20 carbons having on one end a triazole group linked to the 5'-phosphate of the nucleic acid and on the other side a hydroxyl-group. Its insertion was so effective that a fluorescent label on the DNA complementary to the conjugate could be used to visualize fatty acid structures.
authors.affiliation: Center for Fundamental Living Technology (FLinT), Department of Physics, Chemistry and Pharmacy, University of Southern Denmark , Campusvej 55, DK-5230 Odense M, Denmark.
authors.forename: Michael C
authors.initials: MC
authors.lastname: Wamberg
authors.forename: Rafał
authors.initials: R
authors.lastname: Wieczorek
authors.forename: Søren Bo
authors.initials: SB
authors.lastname: Brier
authors.forename: Jan Willem
authors.initials: JW
authors.lastname: de Vries
authors.forename: Minseok
authors.initials: M
authors.lastname: Kwak
authors.forename: Andreas
authors.initials: A
authors.lastname: Herrmann
authors.forename: Pierre-Alain
authors.initials: PA
authors.lastname: Monnard
mesh_terms: D000480:Alkynes / Q000737:chemistry; D001386:Azides / Q000737:chemistry; D002384:Catalysis; D057930:Click Chemistry; D003300:Copper / Q000737:chemistry; D004247:DNA / Q000737:chemistry*; D003652:Decanoic Acids / Q000737:chemistry*; D005456:Fluorescent Dyes / Q000737:chemistry; D005663:Furans / Q000737:chemistry*; D057927:Hydrophobic and Hydrophilic Interactions; D008567:Membranes, Artificial; D011728:Pyridones / Q000737:chemistry*
chemical_list: D000480:Alkynes; D001386:Azides; D003652:Decanoic Acids; D005456:Fluorescent Dyes; D005663:Furans; D008567:Membranes, Artificial; D011728:Pyridones; C543575:bolaamphiphile; C031071:decanoic acid; D003300:Copper; D004247:DNA