Computer-based modeling of the conformation and packing properties of docosahexaenoic acid.

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 int...

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Main Authors: K R Applegate, J A Glomset
Format: Article
Language:English
Published: Elsevier 1988-08-01
Series:Journal of Lipid Research
Online Access:http://www.sciencedirect.com/science/article/pii/S0022227520388052
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spelling doaj-575b54d759894420a93bde9b009ca9e62021-04-25T04:21:09ZengElsevierJournal of Lipid Research0022-22751988-08-01276658680Computer-based modeling of the conformation and packing properties of docosahexaenoic acid.K R ApplegateJ A GlomsetWe 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.http://www.sciencedirect.com/science/article/pii/S0022227520388052
collection DOAJ
language English
format Article
sources DOAJ
author K R Applegate
J A Glomset
spellingShingle K R Applegate
J A Glomset
Computer-based modeling of the conformation and packing properties of docosahexaenoic acid.
Journal of Lipid Research
author_facet K R Applegate
J A Glomset
author_sort K R Applegate
title Computer-based modeling of the conformation and packing properties of docosahexaenoic acid.
title_short Computer-based modeling of the conformation and packing properties of docosahexaenoic acid.
title_full Computer-based modeling of the conformation and packing properties of docosahexaenoic acid.
title_fullStr Computer-based modeling of the conformation and packing properties of docosahexaenoic acid.
title_full_unstemmed Computer-based modeling of the conformation and packing properties of docosahexaenoic acid.
title_sort computer-based modeling of the conformation and packing properties of docosahexaenoic acid.
publisher Elsevier
series Journal of Lipid Research
issn 0022-2275
publishDate 1988-08-01
description 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.
url http://www.sciencedirect.com/science/article/pii/S0022227520388052
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