Hydrochloric Acid → S-Nitrosoglutathione

HRID 501871

반응식

HRID 501871 반응식
[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]

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 124886GlutathioneHCID 23668193Sodium Nitrite

생성물 1

HCID 104858S-Nitrosoglutathione

시약·촉매·용매 1

HCID 962Water용매2회

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-708c303b2e934314910653ca19994034
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07772278B2

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