Hydrochloric Acid → S-Nitrosoglutathione
Reaction equation
[NH2:1][C@H:2]([C:18]([OH:20])=[O:19])[CH2:3][CH2:4][C:5]([NH:7][C@H:8]([C:11]([NH:13][CH2:14][C:15]([OH:17])=[O:16])=[O:12])[CH2:9][SH:10])=[O:6].Cl.[N:22]([O-])=[O:23].[Na+]>O>[NH2:1][C@H:2]([C:18]([OH:20])=[O:19])[CH2:3][CH2:4][C:5]([NH:7][C@H:8]([C:11]([NH:13][CH2:14][C:15]([OH:17])=[O:16])=[O:12])[CH2:9][S:10][N:22]=[O:23])=[O:6]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
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 and 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 vacumm 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 as a pink powder. 1H NMR (D2O) δ: 1.98 (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 vacumm 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-26af818281ce4b989418b1b9d537f82d
- Source dataset
- uspto-grants-2000_07
- Patent number
- US06083515
Reaction notes
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