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 composition comprising a compound having the formula:
wherein R 5 is H, C 1 -C 5 alkyl, or a cation; and each Y is independently H, deuterium, or tritium, and at least one Y is deuterium or tritium, wherein the compound comprises at least 5% of the total number of molecules in the composition.
2. The composition of claim 1 , wherein R 5 is C 1 -C 5 alkyl.
3. The composition of claim 2 , wherein R 5 is ethyl.
4. The composition of claim 1 , wherein two or more Y is deuterium.
5. The composition of claim 4 , wherein the compound has an isotopic load that is in a range from 5% to 30%.
6. The composition compound of claim 4 , wherein the isotopic load is in a range from to 10% to 20%.
7. The composition of claim 4 , wherein the isotopic load is in a range from 5% to 15%.
8. The composition of claim 1 , wherein the compound comprises 5% to 99% of the total number of molecules in the composition.
9. The composition of claim 1 , wherein the compound comprises 5% to 50% of the total numbers of molecules in the composition.
10. A composition comprising a compound having the formula:
wherein R 5 is H, C 1 -C 5 alkyl, or a cation; and each Y is independently H, deuterium, or tritium, and at least one Y is deuterium or tritium, wherein the compound comprises at least 5% of the total number of molecules in the composition.
11. The composition of claim 10 , wherein R 5 is C 1 -C 5 alkyl.
12. The composition of claim 11 , wherein R 5 is ethyl.
13. The composition of claim 10 , wherein two or more Y is deuterium.
14. The composition of claim 13 , wherein the compound has an isotopic load that is in a range from 5% to about 20%.
15. The composition of claim 13 , wherein the isotopic load is in a range from about 10% to about 20%.
16. The composition of claim 13 , wherein the isotopic load is in a range from about 5% to about 15%.
17. The composition of claim 10 , wherein the compound comprises 5% to 99% of the total number of molecules in the composition.
18. The composition of claim 10 , wherein the compound comprises 5% to 50% of the total number of molecules in the composition.
19. The composition of claim 1 or 10 , wherein the composition does not comprise trans isomers of said compound.