Skip to main content
. 2019 Mar 12;119(9):5607–5774. doi: 10.1021/acs.chemrev.8b00538

Table 3. Oxidation Products of Amino Acids.

amino acid product
(1) Oxidative Modifications of Amino Acid Residue Side Chains399,400,409,410
arginine γ-glutamyl semialdehyde, glyco-oxidation adducts
cysteine disulfides, cysteic acid, glutathione cysteine, lipid peroxidation adducts, amino acid oxidation adducts, sulfenic acid, sulfinic acid, sulfonic acid, nitroso-cysteine
glutamic acid oxalic acid, pyruvate adducts, hydro-peroxides
histidine aspartate
asparagine
2-oxo-histidine
4-hydroxy-glutaminic acid
lipid peroxidation adducts
amino acid oxidation adducts
hydro-peroxides
isoleucine hydro-peroxides
leucine 3-hydroxy-leucine, 4-hydroxy-leucine
5-hydroxy-leucine, hydro-peroxides
lysine α-amino-adipic semialdehyde, chloramines, hydro-peroxides
lipid peroxidation adducts, amino acid oxidation adducts
glyco-oxidation adducts
methionine methionine sulfoxide, methionine sulfone
phenylalanine 2-hydroxy-phenylalanine, 3-hydroxy-phenylalanine
4-hydroxy-phenylalanine, 3,4-dihydroxy-phenylalanine
proline glutamic semialdehyde, 4-hydroxyproline, 5-hydroxyproline
pyroglutamic acid, 2-pyrrolidone, hydro-peroxides
threonine 2-amino-3-ketobutyric acid
tryptophan 2-hydroxy-tryptophan, 4-hydroxy-tryptophan
5-hydroxy-tryptophan, 6-hydroxy-tryptophan
7-hydroxy-tryptophan, n-formyl-kynurenine
3-hydroxy-kynurenine, kynurenine
6-nitro-tryptophan, tryptophan-tryptophan cross-linkages
hydro-peroxides
tyrosine 3,4-dihydroxy-phenylalanine, 3-nitro-tyrosine, 3-chloro-tyrosine
3,5-dichloro-tyrosine, tyrosine–tyrosine cross-linkages
tyrosine-oxygen-tyrosine, 2,3-dihydroxy-phenylalanine
hydro-peroxides
(2) Metal-Catalyzed Oxidation of Amino Acid Residues in Proteins400
histidine aspartate, asparagine, oxo-histidine
proline hydroxy-proline, glutamate, γ-glutamyl-semialdehyde
arginine γ-glutamyl-semialdehyde
lysine amino-adipic-semialdehyde
threonine amino-ketobutyrate
tyrosine Tyr–Tyr (dityrosine)
cysteine ESESE (disulfide cross-links)