Levodopa → Acetate

HRID 1703821Notes

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]>>[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].[C:3]([O-:5])(=[O:4])[CH3:2]

Participants

Reactant 2

HCID 6047Levodopa

HCID 124886Glutathione

Product 2

HCID 175Acetate

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

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.

Sources & evidence

ORD record: ord-c6bb98656d1944aa9f3b4b88101c2a00
Source dataset: uspto-grants-1978_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04125626

Reaction notes

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