Reaction equation
[NH2:1][C@@H:2]([CH2:6][CH2:7][C:8]([NH:10][C@H:11]([C:14]([NH:16][CH2:17][C:18]([OH:20])=[O:19])=[O:15])[CH2:12][SH:13])=[O:9])[C:3]([OH:5])=[O:4].Cl.[N:22]([O-])=[O:23].[Na+]>O>[NH2:1][C@H:2]([C:3]([OH:5])=[O:4])[CH2:6][CH2:7][C:8]([NH:10][C@H:11]([C:14]([NH:16][CH2:17][C:18]([OH:20])=[O:19])=[O:15])[CH2:12][S:13][N:22]=[O:23])=[O:9]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
Glutathione (N—(N—L—γ-glutamyl-L-cysteinyl)glycine) (100 g, 0.325 mol) was dissolved in deoxygenated water (200 ml) and 2N HCl (162 ml) at room temperature and then the reaction mixture was cooled to 0° C. With rapid stirring, a solution of sodium nitrite (24.4 g, 0.35 mol) in water (40 ml) was added. Stirring with cooling of the reaction mixture was continued for approximately 1 hour, after which time the pink precipitate which formed was collected by vacuum filtration. The filter cake was resuspended in chilled 40% acetone-water (600 ml) and collected by vacuum filtration. The filter cake was washed with acetone (2×200 ml) and ether (100 ml) and then dried under high vacuum at room temperature in the dark to afford the title compound, N—(N—L—γ-glutamyl-S-Nitroso-L-cysteinyl)glycine, as a pink powder. 1H NMR (D2O): δ1.98 (m, 2H), 2.32 (t, 2H), 3.67 (t, 1H), 3.82 (s, 2H), 3.86 (dd, 1H), 3.98 (dd, 1H), 4.53 (m, 1H).
Workup
- temperaturewith cooling of the reaction mixture
- customafter which time the pink precipitate which formed
- filtrationwas collected by vacuum filtration
- filtrationcollected by vacuum filtration
- washThe filter cake was washed with acetone (2×200 ml) and ether (100 ml)
- customdried under high vacuum at room temperature in the dark
Sources & evidence
- ORD record
- ord-521e1e4b769b4345a49e2df5b7ddbd9f
- Source dataset
- uspto-grants-2007_02
- Patent number
- US07176238B1
Linked notes
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