Phosphatidylcholine-derived bolaamphiphiles via click chemistry.
The copper-catalyzed azide alkyne cycloaddition is employed to modify phosphatidylcholine precursors with sn-2 acyl chains containing terminal alkyne or azide groups. Although the reactions are conducted as biphasic dispersions, the yields are essentially quantitative. Bolaamphiphiles are formed by simply clicking together two phosphatidylcholine alkyne precursors to a central bisazide scaffold. The chemistry introduces polar 1,4-triazole units into the lipophilic region of the bilayer membrane, and the bolaamphiphiles do not form stable vesicles. [structure: see text].
O'Neil
Edward J
EJ
Department of Chemistry & Biochemistry, 251 Nieuwland Science Hall, University of Notre Dame, Notre Dame, Indiana 46556, USA.
DiVittorio
Kristy M
KM
Smith
Bradley D
BD
D000577:Amides / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D003300:Copper / Q000737:chemistry; D003500:Cyclization; D047028:Macrocyclic Compounds / Q000138:chemical synthesis / Q000737:chemistry; D015394:Molecular Structure; D010713:Phosphatidylcholines / Q000737:chemistry*; D013237:Stereoisomerism; D013501:Surface-Active Agents / Q000138:chemical synthesis* / Q000737:chemistry; D013997:Time Factors
D000577:Amides; D047028:Macrocyclic Compounds; D010713:Phosphatidylcholines; D013501:Surface-Active Agents; D003300:Copper