Synthesis and Properties of Dimeric Glycerophospholipid: 2,2':-Dotriacontanedioylbis(l-Palmitoyl-sn-Glycero-3-Phosphocholine)

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.

Formation and stability of micelles and vesicles

“…Also, new types of bolaform surfactants have recently been synthesized that are based on glycosyl ethers [26], or carry bipolar phosphate headgroups [27], or have perfluoroalkylated carbon chains [28], or are based on dimeric glycerophospholipids [29].…”

Bolaamphiphilic Phosphocholines: Structure and Phase Behavior in Aqueous Media

“…Surfactants bearing hydrophilic substituents at the α- and ω-positions of a hydrophobe, so-called “bolaform amphiphiles” , (also called bolaamphiphiles, bolas, or “gemini” surfactants), have recently been the subject of numerous reports. While many of these studies describe the synthesis of phosphatidyl, − amino acid, − carbohydrate, − reactive, or novel hydrophobic linker − bolas, comparatively few of these efforts have focused on the unique structural and physical properties displayed by this class of bioinspired materials. Interest in bolaform amphiphiles within our group has centered on their possible use as a host monolayer membrane matrix for coupled ion and electron-transfer − and supported membrane devices.…”