Design and synthesis of asymmetric acyclic phospholipid bolaamphiphiles.
[structure: see text] A synthetic route was devised for the generation of asymmetric lipid bolaamphiphiles through the sequential esterification of an alkyldioic acid, bearing distinct terminal protecting groups, with propanylamine and lyso-phosphatidylcholine headgroups. Bolaamphiphile self-assembly was investigated in solvent mixes of varying polarity by nuclear magnetic resonance (NMR) and Fourier transform-infrared (FT-IR) spectroscopy, as well as in water by cryo-high-resolution scanning electron microscopy (cryo-HRSEM). We anticipate that asymmetric lipid bolaamphiphiles will provide facile building blocks for engineering a variety of unique membrane-mimetic structures.
Kai
Toshitsugu
T
Department of Surgery, Emory University School of Medicine, Integrated Microscopy & Microanalytical Facility, Emory University, Atlanta, Georgia 30322, USA.
Sun
Xue-Long
XL
Faucher
Keith M
KM
Apkarian
Robert P
RP
Chaikof
Elliot L
EL
D009682:Magnetic Resonance Spectroscopy; D008855:Microscopy, Electron, Scanning; D015394:Molecular Structure; D010743:Phospholipids / Q000138:chemical synthesis / Q000737:chemistry*; D012997:Solvents / Q000737:chemistry; D017550:Spectroscopy, Fourier Transform Infrared
D010743:Phospholipids; D012997:Solvents