Hydrochloric Acid → S-Nitrosoglutathione

HRID 430713

Reaction equation

HRID 430713 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

5

Reactant 3

HCID 313Hydrochloric AcidHCID 124886GlutathioneHCID 23668193Sodium Nitrite

Product 1

HCID 104858S-Nitrosoglutathione

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

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 vaccum 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 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

  1. temperaturewith cooling of the reaction mixture
  2. customafter which time the pink precipitate which formed
  3. filtrationwas collected by vaccum filtration
  4. filtrationcollected by vacuum filtration
  5. washThe filter cake was washed with acetone (2×200 ml) and ether (100 ml)
  6. customdried under high vacuum at room temperature in the dark

Sources & evidence

ORD record
ord-76a117c6e5e142f194f61eace738e289
Source dataset
uspto-grants-2001_11
Patent number
US06323234B1

Linked notes

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