TY - CHAP
T1 - The Chemistry of Peroxynitrite
T2 - Implications for Biological Activity
AU - Goldstein, Sara
AU - Merényi, Gabor
PY - 2008
Y1 - 2008
N2 - In biological systems, nitric oxide (NO) combines rapidly with superoxide (O2 -) to form peroxynitrite ion (ONOO-), a substance that has been implicated as a culprit in many diseases. Peroxynitrite ion is essentially stable, but its protonated form (ONOOH, pKa = 6.5 to 6.8) decomposes rapidly via homolysis of the O-O bond to form about 28% free NO2 and OH radicals. At physiological pH and in the presence of large amounts of bicarbonate, ONOO- reacts with CO2 to produce about 33% NO2 and carbonate ion radicals (CO3 -) in the bulk of the solution. The quantitative role of OH / CO3 - and NO2 radicals during the decomposition of peroxynitrite (ONOOH/ONOO-) under physiological conditions is described in detail. Specifically, the effect of the peroxynitrite dosage rate on the yield and distribution of the final products is demonstrated. By way of an example, the detailed mechanism of nitration of tyrosine, a vital aromatic amino acid, is delineated, showing the difference in the nitration yield between the addition of authentic peroxynitrite and its continuous generation by NO and O2 - radicals.
AB - In biological systems, nitric oxide (NO) combines rapidly with superoxide (O2 -) to form peroxynitrite ion (ONOO-), a substance that has been implicated as a culprit in many diseases. Peroxynitrite ion is essentially stable, but its protonated form (ONOOH, pKa = 6.5 to 6.8) decomposes rapidly via homolysis of the O-O bond to form about 28% free NO2 and OH radicals. At physiological pH and in the presence of large amounts of bicarbonate, ONOO- reacts with CO2 to produce about 33% NO2 and carbonate ion radicals (CO3 -) in the bulk of the solution. The quantitative role of OH / CO3 - and NO2 radicals during the decomposition of peroxynitrite (ONOOH/ONOO-) under physiological conditions is described in detail. Specifically, the effect of the peroxynitrite dosage rate on the yield and distribution of the final products is demonstrated. By way of an example, the detailed mechanism of nitration of tyrosine, a vital aromatic amino acid, is delineated, showing the difference in the nitration yield between the addition of authentic peroxynitrite and its continuous generation by NO and O2 - radicals.
UR - http://www.scopus.com/inward/record.url?scp=42949134909&partnerID=8YFLogxK
U2 - 10.1016/S0076-6879(08)36004-2
DO - 10.1016/S0076-6879(08)36004-2
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C2 - 18237627
AN - SCOPUS:42949134909
SN - 9780123742773
T3 - Methods in Enzymology
SP - 49
EP - 61
BT - Globins and Other Nitric Oxide-Reactive Proteins, Part A
PB - Academic Press Inc.
ER -