Phosphatidylethanol is formed when ethanol substitutes in the transpho
sphatidylation reaction catalyzed by phospholipase D. The structural a
nd thermotropic properties of dipalmitoylphosphatidylethanol and dimyr
istoylphosphatidylethanol have been studied using differential scannin
g calorimetry, fluorescence spectroscopy, and P-31 nuclear magnetic re
sonance, These lipids exist in a bilayer phase with no indication of n
onbilayer phase formation, as shown by P-31 nuclear magnetic resonance
, It was found that the phase behavior of these phospholipids before a
nd during the main chain melting transition is different in 50 mM Tn's
buffer compared to salt solutions. The phase transition behavior and
the 6-propionyl-2-(dimethylamino)naphthalene (Prodan) fluorescence spe
ctra for both lipids are consistent with the formation of the interdig
itated gel phase under certain conditions, Both lipids become interdig
itated in Tris-HCl, and ethanol enhances the formation of this phase.
Comparative studies of the 6-propionyl-2-(dimethylamino)naphthalene sp
ectra in dipalmitoylphosphatidylglycerol, dielaidoylphosphatidylethano
lamine, and dipalmitoyiphosphatidylcholine further elucidate the value
and limitations of this probe as a diagnostic tool for lipid structur
e.