Synthesis of all-cis-1,3-diacylcyclopentane-1,2,3-triol-2-phosphate via acyl group migration in a cyclic diglyceride analog.
The acid-catalyzed isomerization of the diglyceride analog (1,2,3/0)-1,2-dipalmitoylcyclopentane-1,2,3-triol has been used to generate syn-syn-1,3-diacyl-cyclopentane-1,2,3-triol, a required intermediate in the synthesis of a symmetrical all-cis-1,2,3/0-2P cyclopentanoid phosphatidic acid analog. Th...
| Main Authors: | , |
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| Format: | Article |
| Language: | English |
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Elsevier
1979-02-01
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| Series: | Journal of Lipid Research |
| Online Access: | http://www.sciencedirect.com/science/article/pii/S0022227520406406 |
| _version_ | 1818459651686006784 |
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| author | A J Hancock M D Lister |
| author_facet | A J Hancock M D Lister |
| author_sort | A J Hancock |
| collection | DOAJ |
| description | The acid-catalyzed isomerization of the diglyceride analog (1,2,3/0)-1,2-dipalmitoylcyclopentane-1,2,3-triol has been used to generate syn-syn-1,3-diacyl-cyclopentane-1,2,3-triol, a required intermediate in the synthesis of a symmetrical all-cis-1,2,3/0-2P cyclopentanoid phosphatidic acid analog. The all-cis cyclo-phosphatidic acid analog has therefore been obtained in the free acid form and as the diphenyl ester, dimethyl ester, and dipotassium salt derivatives. The compounds have been characterized by microanalysis and spectroscopic methods. The 1,2,3/0-2P analog is now available for comparative studies with the corresponding all-trans cyclophosphatidic acid (1,3/2-2P). |
| first_indexed | 2024-12-14T23:17:45Z |
| format | Article |
| id | doaj.art-1b01817c1b25447890f71b920a03b47f |
| institution | Directory Open Access Journal |
| issn | 0022-2275 |
| language | English |
| last_indexed | 2024-12-14T23:17:45Z |
| publishDate | 1979-02-01 |
| publisher | Elsevier |
| record_format | Article |
| series | Journal of Lipid Research |
| spelling | doaj.art-1b01817c1b25447890f71b920a03b47f2022-12-21T22:44:01ZengElsevierJournal of Lipid Research0022-22751979-02-01202271274Synthesis of all-cis-1,3-diacylcyclopentane-1,2,3-triol-2-phosphate via acyl group migration in a cyclic diglyceride analog.A J HancockM D ListerThe acid-catalyzed isomerization of the diglyceride analog (1,2,3/0)-1,2-dipalmitoylcyclopentane-1,2,3-triol has been used to generate syn-syn-1,3-diacyl-cyclopentane-1,2,3-triol, a required intermediate in the synthesis of a symmetrical all-cis-1,2,3/0-2P cyclopentanoid phosphatidic acid analog. The all-cis cyclo-phosphatidic acid analog has therefore been obtained in the free acid form and as the diphenyl ester, dimethyl ester, and dipotassium salt derivatives. The compounds have been characterized by microanalysis and spectroscopic methods. The 1,2,3/0-2P analog is now available for comparative studies with the corresponding all-trans cyclophosphatidic acid (1,3/2-2P).http://www.sciencedirect.com/science/article/pii/S0022227520406406 |
| spellingShingle | A J Hancock M D Lister Synthesis of all-cis-1,3-diacylcyclopentane-1,2,3-triol-2-phosphate via acyl group migration in a cyclic diglyceride analog. Journal of Lipid Research |
| title | Synthesis of all-cis-1,3-diacylcyclopentane-1,2,3-triol-2-phosphate via acyl group migration in a cyclic diglyceride analog. |
| title_full | Synthesis of all-cis-1,3-diacylcyclopentane-1,2,3-triol-2-phosphate via acyl group migration in a cyclic diglyceride analog. |
| title_fullStr | Synthesis of all-cis-1,3-diacylcyclopentane-1,2,3-triol-2-phosphate via acyl group migration in a cyclic diglyceride analog. |
| title_full_unstemmed | Synthesis of all-cis-1,3-diacylcyclopentane-1,2,3-triol-2-phosphate via acyl group migration in a cyclic diglyceride analog. |
| title_short | Synthesis of all-cis-1,3-diacylcyclopentane-1,2,3-triol-2-phosphate via acyl group migration in a cyclic diglyceride analog. |
| title_sort | synthesis of all cis 1 3 diacylcyclopentane 1 2 3 triol 2 phosphate via acyl group migration in a cyclic diglyceride analog |
| url | http://www.sciencedirect.com/science/article/pii/S0022227520406406 |
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