Synthesis of isotopically labeled R- or S-[
View Patent ↗The present invention is directed to asymmetric chiral labeled glycerols including at least one chiral atom, from one to two 13 C atoms and from zero to four deuterium atoms bonded directly to a carbon atom, e.g., (2S) [1,2- 13 C 2 ]glycerol and (2R) [1,2- 13 C 2 ]glycerol, and to the use of such chiral glycerols in the preparation of labeled amino acids.
1. An asymmetric chiral labeled glycerol selected from the group consisting of (2S) [2- 13 C]glycerol and (2R) [2- 13 C]glycerol and from one to four deuterium atoms bonded directly to a carbon atom with the proviso that where there is only one deuterium atom, it is bonded to a terminal carbon atom.
2. An asymmetric chiral labeled glycerol selected from the group consisting of (2S) [1,2- 13 C 2 ]glycerol and (2R) [1,2- 13 C 2 ]glycerol and from zero to four deuterium atoms bonded directly to a carbon atom.
3. An asymmetric chiral labeled glycerol selected from the group consisting of (2S, 3S) [1,2- 13 C 2 , 3- 2 H]glycerol, (2R, 3R) [1,2- 13 C 2 , 3- 2 H]glycerol, (2S, 3R) [1,2- 13 C 2 , 3- 2 H]glycerol, (2R, 3S) [1,2- 13 C 2 , 3- 2 H]glycerol, (2S) [1- 13 C, 2- 2 H]glycerol and (2R) [1- 13 C, 2- 2 H]glycerol.
4. The asymmetric chiral labeled glycerol of claim 2 wherein said glycerol is selected from the group consisting of (2S) [1,2- 13 C 2 , 3- 2 H]glycerol and (2R) [1,2- 13 C 2 , 3- 2 H]glycerol.
5. The asymmetric chiral labeled glycerol of claim 2 wherein said glycerol is selected from the group consisting of (2S) [1,2- 13 C 2 , 3- 2 H 2 ]glycerol and (2R) [1,2- 13 C 2 , 3- 2 H 2 ]glycerol.
6. The asymmetric chiral labeled glycerol of claim 1 wherein said glycerol is selected from the group consisting of (2S) [1- 2 H, 2- 13 C]glycerol and (2R) [1- 2 H, 2- 13 C]glycerol.
7. The asymmetric chiral labeled glycerol of claim 1 wherein said glycerol is selected from the group consisting of (2S) [1- 2 H 2 , 2- 13 C]glycerol and (2R) [1- 2 H 2 , 2- 13 C]glycerol.
8. An asymmetric chiral labeled glycerol selected from the group consisting of (1S, 2S) [1- 13 C, 1- 2 H]glycerol, (1R, 2R) [1- 13 C, 1- 2 H]glycerol, (1S, 2R) [1- 13 C, 1- 2 H]glycerol and (1R, 2S) [1- 13 C, 1- 2 H]glycerol.
9. An asymmetric chiral labeled glycerol including two chiral atoms, from one to two 13 C atoms and from one to four deuterium atoms bonded directly to a carbon atom.
10. The asymmetric chiral labeled glycerol of claim 9 wherein said glycerol is selected from the group consisting of
(1R, 2R) [1- 13 C, 1,2- 2 H 2 ]glycerol, (1S, 2S) [1- 13 C, 1,2- 2 H 2 ]glycerol,
(1S, 2R) [1- 13 C, 1,2- 2 H 2 ]glycerol, (1R, 2S) [1- 13 C, 1,2- 2 H 2 ]glycerol,
(1R, 2R) [1- 13 C, 1,3- 2 H 3 ]glycerol, (1S, 2S) [1- 13 C, 1,3- 2 H 3 ]glycerol,
(1S, 2R) [1- 13 C, 1,3- 2 H 3 ]glycerol and (1R, 2S) [1- 13 C, 1,3- 2 H 3 ]glycerol.
11. The asymmetric chiral labeled glycerol of claim 9 wherein said glycerol is selected from the group consisting of
(1R, 2R) [1- 13 C, 1,2,3,3- 2 H 4 ]glycerol, (1S, 2S) [1- 13 C, 1,2,3,3- 2 H 4 ]glycerol,
(1S, 2R) [1- 13 C, 1,2,3,3- 2 H 4 ]glycerol and (1R, 2S) [1- 13 C, 1,2,3,3- 2 H 4 ]glycerol.
12. The asymmetric chiral labeled glycerol of claim 9 wherein said glycerol is selected from the group consisting of
(1R, 2R) [1,2- 13 C 2 , 1- 2 H]glycerol, (1S, 2S) [1,2- 13 C 2 , 1- 2 H]glycerol,
(1S, 2R) [1,2- 13 C 2 , 1- 2 H]glycerol and (1R, 2S) [1,2- 13 C 2 , 1- 2 H]glycerol.
13. The asymmetric chiral labeled glycerol of claim 9 wherein said glycerol is selected from the group consisting of
(1R, 2R) [1,2- 13 C 2 , 1,2- 2 H 2 ]glycerol, (1S, 2S) [1,2- 13 C 2 , 1,2- 2 H 2 ]glycerol,
(1S, 2R) [1,2- 13 C 2 , 1,2- 2 H 2 ]glycerol and (1R, 2S) [1,2- 13 C 2 , 1,2- 2 H 2 ]glycerol.
14. The asymmetric chiral labeled glycerol of claim 9 wherein said glycerol is selected from the group consisting of
(1R, 2R) [1,2- 13 C 2 , 1,3- 2 H 3 ]glycerol, (1S, 2S) [1,2- 13 C 2 , 1,3- 2 H 3 ]glycerol,
(1S, 2R) [1,2- 13 C 2 , 1,3- 2 H 3 ]glycerol and (1R, 2S) [1,2- 13 C 2 , 1,3- 2 H 3 ]glycerol.
15. The asymmetric chiral labeled glycerol of claim 9 wherein said glycerol is selected from the group consisting of
(1R, 2R) [1,2- 13 C 2 , 1,2,3,3- 2 H 4 ]glycerol, (1S, 2S) [1,2- 13 C 2 , 1,2,3,3- 2 H 4 ]glycerol,
(1S, 2R) [1,2- 13 C 2 , 1,2,3,3- 2 H 4 ]glycerol and (1R, 2S) [1,2- 13 C 2 , 1,2,3,3- 2 H 4 ]glycerol.