Hydrochloric Acid → S-Nitrosoglutathione

HRID 270755

Reaktionsgleichung

Reaktionsgleichung von HRID 270755
[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]

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 124886GlutathioneHCID 23668193Sodium Nitrite

Produkt 1

HCID 104858S-Nitrosoglutathione

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel2×

Versuchsvorschrift

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).

Aufarbeitung

  1. temperaturewith cooling of the reaction mixture
  2. customafter which time the pink precipitate which formed
  3. filtrationwas collected by vacuum 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

Quellen und Nachweise

ORD-Eintrag
ord-3aa3c0bcebd34695a6db2e03424dc03e
Quelldatensatz
uspto-grants-2008_11
Patentnummer
US07449595B2

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