L-Tyrosine → (2S)-3-(4-hydroxyphenyl)-2-nitramidopropanoic acid

HRID 1629666Notes

Reaction equation

HRID 1629666 reaction equation
[NH2:1][C@H:2]([C:11]([OH:13])=[O:12])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1.[N:14]([O:16][O-])=[O:15]>P([O-])([O-])([O-])=O>[N+:14]([NH:1][C@H:2]([C:11]([OH:13])=[O:12])[CH2:3][C:4]1[CH:5]=[CH:6][C:7]([OH:10])=[CH:8][CH:9]=1)([O-:16])=[O:15]

Participants

4

Reactant 2

HCID 6057L-Tyrosine2×HCID 104806Peroxynitrite radical

Product 1

HCID 9834478(2S)-3-(4-hydroxyphenyl)-2-nitramidopropanoic acid

Reagents, catalysts & solvents 1

HCID 1061PhosphateSolvent

Procedure

Nitration of L-tyrosine: Peroxynitrite (0.44 μmol) was reacted with 0.16 μmol of L-tyrosine in 2 mL phosphate buffer solution, pH 7.4 at T=24° C. for 5 min. The concentration of such formed nitrotyrosine was estimated by recording the 438 nm absorbance (ε=4200 M−1cm−1) of basified solutions (via the addition of 0.2 ml of 7.8 M NaOH). The same experiments were repeated in the presence of either 0.1 μmol 1-Fe or 1-Mn.

Sources & evidence

ORD record
ord-cede1cb35eb9453bb950f72addd9404b
Source dataset
uspto-grants-2014_07
Patent number
US08791099B2

Reaction notes

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