Processes for isotopic modification of polyunsaturated fatty acids and derivatives thereof
Disclosed herein are methods for preparing isotopically modified polyunsaturated lipids containing 1,4-diene systems involving selective isotopic modification of one or more bis-allylic positions of the polyunsaturated lipids in the presence of a transition metal catalyst.
1. A ruthenium complex of the formula I:
wherein R and R′ comprise the remainder of linolenic acid, arachidonic acid, eicosapentaenoic acid, or docosahexaenoic acid or an ester thereof; wherein when present, the ester is a C 1 -C 21 alkyl ester;
wherein the ruthenium complex further comprises a cyclopentadiene (Cp) ligand; and
wherein ruthenium in the ruthenium complex is in the +1 oxidation state (Ru +1 ).
2. The complex of claim 1 , wherein R and R′ comprise the remainder of linolenic acid.
3. The complex of claim 1 , wherein R and R′ comprise the remainder of arachidonic acid.
4. The complex of claim 1 , wherein R and R′ comprise the remainder of eicosapentaenoic acid.
5. The complex of claim 1 , wherein R and R′ comprise the remainder of docosahexaenoic acid.
6. The complex of claim 1 , wherein R and R′ comprise the remainder of linolenic C 1 -C 21 alkyl ester.
7. The complex of claim 1 , wherein R and R′ comprise the remainder of arachidonic C 1 -C 21 alkyl ester.
8. The complex of claim 1 , wherein R and R′ comprise the remainder of eicosapentaenoic C 1 -C 21 alkyl ester.
9. The complex of claim 1 , wherein R and R′ comprise the remainder of docosahexaenoic C 1 -C 21 alkyl ester.
10. The complex of claim 1 , wherein R and R′ comprise the remainder of linolenic ethyl ester.
11. The complex of claim 1 , wherein R and R′ comprise the remainder of arachidonic ethyl ester.
12. The complex of claim 1 , wherein R and R′ comprise the remainder of eicosapentaenoic ethyl ester.
13. The complex of claim 1 , wherein R and R′ comprise the remainder of docosahexaenoic ethyl ester.