Acetone → S-Nitrosoglutathione

HRID 1950672Notes

Reaction equation

HRID 1950672 reaction equation
[CH2:1]([C@H:16]([NH2:20])[C:17]([OH:19])=[O:18])[CH2:2][C:3]([NH:5][C@H:6]([C:9]([NH:11][CH2:12][C:13]([OH:15])=[O:14])=[O:10])[CH2:7][SH:8])=[O:4].[N:21]([O-])=[O:22].[Na+].CC(C)=O>O.Cl>[N:21]([S:8][CH2:7][C@@H:6]([C:9]([NH:11][CH2:12][C:13]([OH:15])=[O:14])=[O:10])[NH:5][C:3](=[O:4])[CH2:2][CH2:1][C@@H:16]([C:17]([OH:19])=[O:18])[NH2:20])=[O:22]

Participants

6

Reactant 3

HCID 180AcetoneHCID 124886GlutathioneHCID 23668193Sodium Nitrite

Product 1

HCID 104858S-NitrosoglutathioneYield 76%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Conditions

Temperature
5 °C

Procedure

1.53 g (5 mmol) L-glutathione (GSH) was dissolved in a mixture of 5.5 ml water and 2.5 ml (2 N) aqueous HCl solution cooled in ice bath, then 0.345 g (mmol) sodium nitrite was added. The mixture was stirred for 40 min at 5° C., then 10 ml acetone was added and the solution was stirred for further 10 min. The precipitated brown deposit was filtered and subsequently washed with ice-cold water (5×1 ml), acetone (3×10 ml) and ether (3×10 ml). Thus 1.29 g (3.8 mmol) of S-nitrosoglutathione was obtained (76% yield).

Workup

  1. temperaturecooled in ice bath
  2. stirringthe solution was stirred for further 10 min
  3. filtrationThe precipitated brown deposit was filtered
  4. washsubsequently washed with ice-cold water (5×1 ml), acetone (3×10 ml) and ether (3×10 ml)

Sources & evidence

ORD record
ord-c440ce77aabc4262a5a23a0eeec3d2c7
Source dataset
uspto-grants-2013_03
Patent number
US08404266B2

Reaction notes

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