Design and synthesis of asymmetric acyclic phospholipid bolaamphiphiles

J Org Chem. 2005 Apr 1;70(7):2606-15. doi: 10.1021/jo048167o.

Abstract

[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.

Publication types

  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Magnetic Resonance Spectroscopy
  • Microscopy, Electron, Scanning
  • Molecular Structure
  • Phospholipids / chemical synthesis
  • Phospholipids / chemistry*
  • Solvents / chemistry
  • Spectroscopy, Fourier Transform Infrared

Substances

  • Phospholipids
  • Solvents