Hydrochloric Acid → S-Nitrosoglutathione

HRID 270755

反応式

HRID 270755 の反応式
[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]

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 124886GlutathioneHCID 23668193Sodium Nitrite

生成物 1

HCID 104858S-Nitrosoglutathione

試薬・触媒・溶媒 1

HCID 962Water溶媒2 回

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-3aa3c0bcebd34695a6db2e03424dc03e
出典データセット
uspto-grants-2008_11
特許番号
US07449595B2

関連ノート

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