Synthesis and characterization of 1,2-dimyristoylamido-1,2-deoxyphosphatidylcholine as an artificial boundary lipid

Junzo Sunamoto, Mitsuaki Goto, Kiyoshi Iwamoto, Hiroki Kondo, Toshinori Sato

Research output: Contribution to journalArticle

45 Citations (Scopus)

Abstract

The synthesis and characterization of an artificial boundary lipid, 1,2-dimyristoylamido-1,2-deoxyphosphatidylcholine (DDPC), are described. DDPC has two amide bonds instead of ester bonds of regular lecithins such as 1,2-dimyristoylphosphatidylcholine (DMPC). In differential scanning calorimetry (DSC) measurements, DDPC gave two endothermic peaks: one was at 18.0°C (ΔH = 10.74 kJ·mol-1) and the other at 23.0°C (ΔH = 12.91 kJ·mol-1). The former peak was sharp and considered to be the phase transition of the hydrocarbon region, while the latter was assigned to the melt of the hydrogen-belt formed by the amide groups of DDPC. Addition of DDPC to DMPC made the DMPC membrane less fluid in the region close to the surface, and significantly increased the reconstitution efficiency of glycophorin into the membrane. This effect of DDPC was much larger than that of naturally occurring lipid, sphingomyelin.

Original languageEnglish
Pages (from-to)209-219
Number of pages11
JournalBBA - Biomembranes
Volume1024
Issue number2
DOIs
Publication statusPublished - 1990 May 24
Externally publishedYes

Fingerprint

Dimyristoylphosphatidylcholine
Lipids
Amides
Glycophorin
Membranes
Sphingomyelins
Lecithins
Phase Transition
Differential Scanning Calorimetry
Hydrocarbons
Hydrogen
Differential scanning calorimetry
Esters
Phase transitions
Fluids
1,2-dimyristoylamido-1,2-deoxyphosphatidylcholine

Keywords

  • Boundary lipid, artificial
  • DSC
  • Fluorescence polarization
  • Lipid-protein interaction
  • Membrane fluidity

ASJC Scopus subject areas

  • Biophysics
  • Biochemistry
  • Cell Biology

Cite this

Synthesis and characterization of 1,2-dimyristoylamido-1,2-deoxyphosphatidylcholine as an artificial boundary lipid. / Sunamoto, Junzo; Goto, Mitsuaki; Iwamoto, Kiyoshi; Kondo, Hiroki; Sato, Toshinori.

In: BBA - Biomembranes, Vol. 1024, No. 2, 24.05.1990, p. 209-219.

Research output: Contribution to journalArticle

Sunamoto, Junzo ; Goto, Mitsuaki ; Iwamoto, Kiyoshi ; Kondo, Hiroki ; Sato, Toshinori. / Synthesis and characterization of 1,2-dimyristoylamido-1,2-deoxyphosphatidylcholine as an artificial boundary lipid. In: BBA - Biomembranes. 1990 ; Vol. 1024, No. 2. pp. 209-219.
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