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Synthesis of long chain n-3 and n-6 fatty acids having a photoactive conjugated tetraene group
- Source :
- Chemistry and Physics of Lipids. 130:145-158
- Publication Year :
- 2004
- Publisher :
- Elsevier BV, 2004.
-
Abstract
- Fatty acids of the n-3 and n-6 families containing a photoactive conjugated tetraene group near the carboxylate were prepared from several naturally occurring fatty acids by sequential iodolactonization and treatment with excess 1,8-diazabicyclo[5.4.0]undec-7-ene. The new conjugated fatty acids include 5E,7E,9E,11Z,14Z- and 5E,7E,9E,11E,14Z-eicosapentaenoic acids derived from arachidonic acid; 5E,7E,9E,11Z,14Z,17Z- and 5E,7E,9E,11E,14Z,17Z-eicosahexaenoic acids from eicosapentaenoic acid; and 4E,6E,8E,10Z,13Z,16Z,19Z- and 4E,6E,8E,10E,13Z,16Z,19Z-docosaheptaenoic acids from docosahexaenoic acid. All of the newly synthesized fatty acids were characterized by UV, 1H NMR and mass spectroscopy. These new products represent the first examples of directed conjugation of methylene interrupted double bond systems. The products can be synthesized in gram quantities and in high yields (>50%). Interestingly, it did not prove possible to synthesize fatty acids having a triene group near the carboxyl group even using mild conditions and different synthetic approaches. Once initiated, the isomerization always continued until a tetraene group was formed. Because of the sensitivity of the tetraene group to light, these fatty acids have the potential for being used in tracking fatty acid movements in cells employing fluorescence techniques and in UV light-induced cross linking to membrane proteins.
- Subjects :
- chemistry.chemical_classification
Molecular Structure
Trimethylsilyl
Photochemistry
Parinaric Acid
Stereochemistry
Organic Chemistry
Iodolactonization
Fatty acid
Cell Biology
Biochemistry
Eicosapentaenoic acid
Lactones
chemistry.chemical_compound
chemistry
Spectrophotometry
Docosahexaenoic acid
Fatty Acids, Unsaturated
Organic chemistry
Arachidonic acid
Molecular Biology
Chromatography, High Pressure Liquid
Iodine
Polyunsaturated fatty acid
Subjects
Details
- ISSN :
- 00093084
- Volume :
- 130
- Database :
- OpenAIRE
- Journal :
- Chemistry and Physics of Lipids
- Accession number :
- edsair.doi.dedup.....61d2df724c0b13ae6f875598767daf88