IP Library Granted Patent US 7,321,070
Granted Patent B2
US 7,321,070 · App. 10/629,982 · Granted Jan 22, 2008

Synthesis of isotopically labeled R- or S-[

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Quick Facts
Patent No.
US 7,321,070
App. No.
10/629,982
Granted
Jan 22, 2008
Kind
B2
Abstract

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.

Claims (29)

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.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 7, 2018
From: LOS ALAMOS NATIONAL SECURITY, LLC
To: TRIAD NATIONAL SECURITY, LLC
Reel/Frame 047446/0849 →