Levodopa → N-(4-Amino-4-carboxy-1-hydroxybutylidene)-3-hydroxytyrosine

HRID 1703822Notes

Reaction equation

HRID 1703822 reaction equation
[NH2:1][C@@H:2]([CH2:6][CH2:7][C:8](N[C@H](C(NCC(O)=O)=O)CS)=[O:9])[C:3]([OH:5])=[O:4].[O:21]=[C:22]([C@H:24]([CH2:26][C:27]1[CH:34]=[C:32]([OH:33])[C:30]([OH:31])=[CH:29][CH:28]=1)[NH2:25])[OH:23]>C(O)C(N)(CO)CO>[NH2:1][C@H:2]([C:3]([OH:5])=[O:4])[CH2:6][CH2:7][C:8]([NH:25][C@@H:24]([CH2:26][C:27]1[CH:34]=[C:32]([OH:33])[C:30]([OH:31])=[CH:29][CH:28]=1)[C:22]([OH:23])=[O:21])=[O:9]

Participants

4

Reactant 2

HCID 6047LevodopaHCID 124886Glutathione

Product 1

HCID 115303N-(4-Amino-4-carboxy-1-hydroxybutylidene)-3-hydroxytyrosine

Reagents, catalysts & solvents 1

HCID 6503Tris(hydroxymethyl)aminomethaneSolvent

Procedure

Glutathione and L-DOPA were incubated with a partially purified preparation of sheep kidney γ-glutamyl transpeptidase. γ-Glutamyl-DOPA was isolated from the incubation mixture by preparative ion exchange chromatography on a Dowex-1 (acetate) column. 6.14 of glutathione (0.02 mole) and 1.97 g of L-DOPA (0.01 mole) were dissolved in 200 ml of 1 M Tris (base) solution. 2.5 ml of γ-glutamyl transpeptidase solution (100 units/ml) were added and the flask was flushed with nitrogen to protect DOPA from oxidation and the mixture was incubated at 37° for 6 hours. L-γ-glutamyl-L-3,4-dihydroxyphenylalanine (γ-glutamyl-DOPA) was isolated by ion exchange chromatography as in Example 1. It emerges from the column when approximately 2 liters of the eluent passed through the column. Unreacted. glutathione, free glutamate and cysteinylglycine emerge from the column in earlier fractions.

Workup

  1. addition2.5 ml of γ-glutamyl transpeptidase solution (100 units/ml) were added
  2. customthe flask was flushed with nitrogen

Sources & evidence

ORD record
ord-f84943c021b04bb890971161fb2a6e3a
Source dataset
uspto-grants-1978_11
Patent number
US04125626

Reaction notes

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