Glutathione → S-(1,2-Dicarboxyethyl)glutathione

HRID 1090175노트

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HRID 1090175 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].[C:21]([OH:28])(=[O:27])/[CH:22]=[CH:23]\[C:24]([OH:26])=[O:25]>O.II>[C:24]([CH:23]([S:13][CH2:12][C@@H:11]([C:14]([NH:16][CH2:17][C:18]([OH:20])=[O:19])=[O:15])[NH:10][C:8](=[O:9])[CH2:7][CH2:6][C@@H:2]([C:3]([OH:5])=[O:4])[NH2:1])[CH2:22][C:21]([OH:28])=[O:27])([OH:26])=[O:25]

참가 물질

5

반응물 2

HCID 124886GlutathioneHCID 444266Maleic Acid

생성물 1

HCID 9802383S-(1,2-Dicarboxyethyl)glutathione수율 71%

시약·촉매·용매 2

HCID 807Iodine촉매HCID 962Water용매

실험 절차

Glutathione (9.2 g) and 5.0 g of maleic acid are dissolved in 150 ml of water and the solution is allowed to stand at room temperature for 12 hours. The reaction mixture is sampled (one or two drops) and one drop of 0.01N I2 test solution is added to the sample. After confirming, in this manner, that there is no more iodine consumption, 6.6 g of copper acetate (monohydrate) is added to the reaction mixture. If a precipitate, which is small in amount, is found, the precipitate is filtered off. The filtrate is concentrated to about 70 ml, ethanol is added to the concentrate, and the resulting blue copper salt precipitate is collected by filtration. This is recrystallized from water-ethanol. This copper salt is further dissolved in 200 ml of water, hydrogen sulfide is passed through the solution to cause precipitation of copper sulfide, and the precipitate is filtered off. The filtrate is concentrated under reduced pressure and ethanol is added to the residue, whereupon white crystals appear. The crystals are collected by filtration, washed with ethanol and recrystallized from water-ethanol to give about 9 g of the desired compound as white amorphous crystals (hygroscopic).

후처리

  1. additionis added to the sample
  2. customno more iodine consumption, 6.6 g of copper acetate (monohydrate)
  3. additionis added to the reaction mixture
  4. filtrationthe precipitate is filtered off
  5. concentrationThe filtrate is concentrated to about 70 ml, ethanol
  6. additionis added to the concentrate
  7. filtrationthe resulting blue copper salt precipitate is collected by filtration
  8. customThis is recrystallized from water-ethanol
  9. dissolutionThis copper salt is further dissolved in 200 ml of water
  10. customprecipitation of copper sulfide
  11. filtrationthe precipitate is filtered off
  12. concentrationThe filtrate is concentrated under reduced pressure and ethanol
  13. additionis added to the residue, whereupon white crystals
  14. filtrationThe crystals are collected by filtration
  15. washwashed with ethanol
  16. customrecrystallized from water-ethanol

출처 및 근거

ORD 기록
ord-efcb87160134422b969b80ffef71cc1c
출처 데이터셋
uspto-grants-1992_01
특허 번호
US05081149

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