Synthesis and properties of dimeric glycerophospholipid: 2,2'-dotriacontanedioylbis(1-palmitoyl-sn-glycero-3-phosphocholine)

J Biochem. 1996 Jan;119(1):115-9. doi: 10.1093/oxfordjournals.jbchem.a021195.

Abstract

2,2'-Dotriacontanedioylbis(1-palmitoyl-sn-glycero-3-phosphocholine ) was synthesized chemically as a dimeric version of 1,2-dipalmitoyl-sn-glycero-3-phosphocholine. Upon sonication in water, the bipolar lipid furnished a planar membrane of about 50 Angstrom thickness with gel-to-liquid crystalline phase transition constants of Tm = 53.4 degrees C, DeltaH = 20.9 kcal/mol, and DeltaS = 64.0 e.u. In an air/water interface, the lipid displayed unique surface pressure-surface area isotherms with a limiting area of 105-190 Angstrom/molecule at 10-20 degrees C. The lipid was a substrate of phospholipase A2 (Naja mocambique), which afforded 1-palmitoyl-sn-glycero-3-phosphocholine and dotriacontanedioic acid as final products.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Buffers
  • Chromatography, High Pressure Liquid
  • Chromatography, Thin Layer
  • Hydrolysis
  • Lipid Bilayers
  • Liposomes / chemistry
  • Phosphatidylcholines / chemical synthesis
  • Phosphatidylcholines / chemistry*
  • Phosphatidylcholines / metabolism
  • Phospholipases A / metabolism
  • Phospholipases A2
  • Surface Properties
  • Water

Substances

  • Buffers
  • Lipid Bilayers
  • Liposomes
  • Phosphatidylcholines
  • Water
  • 1,2-ditetradecylphosphatidylcholine
  • Phospholipases A
  • Phospholipases A2