Chemistry Reference
In-Depth Information
TABLE 5.7. Products and Intermediates Detected in Peroxynitrite-Damaged Amino
Acids
Amino Acid
Product
Reference
Cysteine
disulfide (RSSR)
[205]
Sulfenic acid
(RSOH)
[205, 263, 270]
Sulfinic acid (RSO
2
H)
[205]
Sulfonic acid (RSO
3
H)
[205]
Nitrosocysteine (RSNO)
[271, 275]
Nitrocysteine (RSNO
2
)
[271]
Thiyl radical (RS
•
)
[276]
(disulfide radical anion (RSSR
−•
)
[41]
Sulfinyl radical (RSO
•
)
[41]
Sulfinic acid (RSO
2
H)
[205]
Cysteine sulfinic acid
Sulfonates
[216]
Hypotaurine
Sulfonates
[216]
Methionine
Methionine sulfoxide
[206, 269, 273]
Tryptophan
5- and 6-Nitrotryptophan
[274, 405]
Hydroxytryptophan
[274]
N-Formylkynurenine
[274, 277]
Hydropyrroloindole
[277]
Oxindole
[277]
Tryptophanyl radical
[278]
Tyrosine
3-Nitrotyrosine
[199, 207, 212, 279, 280]
3-Hydroxytyrosine
[212, 279]
dityrosine
[279, 280]
3,5-dinitrotyrosine
[406]
Tyrosyl radical
[287]
Phenylalanine
o
-,
m
- and
p
-Tyrosine
[279]
Nitrophenylalanine
[279]
Nitrotyrosine
[279]
dityrosine
[279]
Histidine
Oxo-histidine
[240]
Nitrohistidine
[240]
Histidinyl radical
[240]
Adapted from Alvarez and Radi [248].
ONOOH RS
+
−
→
NO RSOH
−
2
+
(5.43)
RSOH RS
+
−
→
RSSR OH
+
−
.
(5.44)
disulfide does not usually react with peroxynitrite [267]. However, reactive
disulfide in lipoic acid displayed reactivity with peroxynitrite (1.4 × 10
3
/M/s),
forming thiosulfinate or disulfide-oxide [267]. Sulfinate, such as taurine and
cysteine sulfinic acid, also had reactivity with peroxynitrite, but at least an
order of magnitude slower than that of sulfur-containing amino acids (Table
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