Site-specific isotopic labeling of 1,4-diene systems
Methods for preparing isotopically modified 1,4-diene systems from non-isotopically modified 1,4-dienes involve selective oxidation of one or more bis-allylic position(s), or the preparation of isotopically modified 1,4-diene systems via trapping pi-allylic complexes with a source of deuterium or tritium. Such methods are useful for preparing isotopically modified polyunsaturated lipid including polyunsaturated fatty acids and polyunsaturated fatty acid derivatives.
1. A compound of the formula:
wherein: R 5 is an unsubstituted C 1 -C 5 alkyl group; and each Y is independently deuterium or tritium.
2. The compound of claim 1 , wherein R 5 is an unsubstituted ethyl.
3. The compound of claim 1 , wherein each Y is deuterium.
4. The compound of claim 1 , wherein R 5 is an unsubstituted ethyl; and each Y is deuterium.
5. The compound of claim 1 , wherein the compound has an isotopic load that is in a range of from about 25% to about 30%.
6. A composition comprising
and one or both of eicosapentaenoic acid and docosahexaenoic acid, wherein:
R 5 is an unsubstituted C 1 -C 5 alkyl group; and
each Y is independently deuterium or tritium.
7. The composition of claim 6 , wherein R 5 is an unsubstituted ethyl.
8. The composition of claim 6 , wherein each Y is deuterium.
9. The composition of claim 6 , wherein R 5 is an unsubstituted ethyl; and each Y is deuterium.
10. The composition of claim 6 , wherein the isotopic loads of the compounds are independently in a range of from about 25% to about 30%.
11. The composition of claim 6 , wherein the composition has an isotopic purity in a range of about 5% to about 99%.
12. The composition of claim 6 , wherein the composition has an isotopic purity in a range of about 5% to about 50%.
13. The composition of claim 6 , wherein the composition has an isotopic purity in a range of about 5% to about 25%.