A unique surface interaction for perdeuterated ethanol and 1-butanol w
ith dipalmitoylphosphatidylcholine (DPPC)/monosialoganglioside (G(M1))
multilamellar vesicles can be detected from the fast exchange averagi
ng of the nuclear quadrupole coupling constant of the alcohol in the f
ree and bound states using deuterium NMR. At 1.0% perdeuterated ethano
l or 0.5% perdeuterated 1-butanol, a small splitting of the alcohol re
sonance(s) was detected in the liquid-crystalline phase, but not in th
e gel phase of the bilayer. The observed splitting is proportional to
the fraction of alcohol bound and is dependent on temperature, alcohol
, and G(M1) concentrations. The splitting was only observed in the pre
sence of negatively charged G(M1) but not neutral asialoganglioside (a
sialo-G(M1)) in DPPC multilamellar vesicles. The observed splitting de
creased with the addition of Ca2+ or Mg2+ ions. This effect was revers
ed upon the addition of chelating agents. It is proposed that the uniq
ue surface interaction for alcohol may result from small surface pertu
rbations of the phosphatidylcholine head groups by the negatively char
ged sialic moieties of neighboring G(M1) molecules in the bilayer.