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Journal of Lipid Research, Vol 27, 658-680, Copyright © 1986 by Lipid Research, Inc.
KR Applegate and JA Glomset
We used a molecular modeling approach to search for a conformation of
docosahexaenoic acid (DHA) that might uniquely influence acyl chain packing
in cell membranes. Studies of DHA models containing six cis double bonds
and five intervening methylene groups identified two conformations of
special interest. Both had nearly straight chain axes formed by methylene
carbon alignment. In one, the carbons of the six double bonds projected
outward from the methylene axis in two nearly perpendicular planes to form
an angle iron-shaped molecule. In the other, the double-bond carbons
projected outward from the axis at nearly 90 degree-intervals to form a
helix. Studies of packed arrays of these hexaenes with or without saturated
hydrocarbons showed that tight intermolecular packing arrangements were
possible, particularly in the case of the angle iron-shaped molecules. The
planar surfaces of two or more such molecules could be brought into contact
"back to back," while the interplanar "V groove" of each molecule could
come into close apposition with a saturated chain. Because a similar mixed
chain packing arrangement was found also for 1,2 diacylglycerols, these
results raise the possibility that DHA may, in certain circumstances,
promote tight, regular acyl chain packing arrays in DHA-rich membranes.
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Computer-based modeling of the conformation and packing properties of docosahexaenoic acid
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