Nitration and nitrosation of N-acetyl-l-tryptophan and tryptophan residues in proteins by various reactive nitrogen species

Suzuki, Toshinori; Mower, Howard F.; Friesen, Marlin D.; Gilibert, Isabelle; Sawa, Tomohiro; Ohshima, Hiroshi

doi:10.1016/j.freeradbiomed.2004.05.030

Cited by 90 publications

(81 citation statements)

References 52 publications

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“…Significantly lower yields (ca. 1 -2%) have been observed for the peroxynitrite-dependent nitrosation of thiols [17 -19] and of indole derivatives [20] [21].…”

mentioning

confidence: 99%

The Reaction of Peroxynitrite with Morpholine (Secondary Amines) Revisited: The Overlooked Hydroxylamine Formation

Kirsch¹,

Korth²,

Wensing³

et al. 2006

Helvetica Chimica Acta

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In memoriam Hanns FischerThe reaction of peroxynitrite/peroxynitrous acid with morpholine as a model compound for secondary amines is reinvestigated in the absence and presence of carbon dioxide. The concentration-and pHdependent formation of N-nitrosomorpholine and N-nitromorpholine as reported in three previous papers ([25] [26] [14]) is basically confirmed. However, 13 C-NMR spectroscopic product analysis shows that, in the absence of CO 2 , N-hydroxymorpholine is, at pH ! 7, the major product of this reaction, even under anaerobic conditions. The formation of N-hydroxymorpholine has been overlooked in the three cited papers. Additional (ring-opened) oxidation products of morpholine are also detected. The data account for radical pathways for the formation of these products via intermediate morpholinederived aminyl and a-aminoalkyl radicals. This is further supported by EPR-spectrometric detection of morpholine-derived nitroxide radicals, i.e., morpholin-4-yloxy radicals. N-Nitrosomorpholine, however, is very likely formed by electrophilic attack of peroxynitrite-derived N 2 O 4 .15 N-CIDNP Experiments establish that, in the presence of CO 2 , N-nitro-and C-nitromorpholine are generated by radical recombination. The present results are in full accord with a fractional (28 AE 2%) homolytic decay of peroxynitrite/peroxynitrous acid with release of free hydroxyl and nitrogen dioxide radicals.

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“…Significantly lower yields (ca. 1 -2%) have been observed for the peroxynitrite-dependent nitrosation of thiols [17 -19] and of indole derivatives [20] [21].…”

mentioning

confidence: 99%

The Reaction of Peroxynitrite with Morpholine (Secondary Amines) Revisited: The Overlooked Hydroxylamine Formation

Kirsch¹,

Korth²,

Wensing³

et al. 2006

Helvetica Chimica Acta

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“…These reactions may result in structural alterations and loss of enzymatic activity implicated in a variety of diseases, including several neurodegenerative ailments as well as in aging. Specific nitration of tryptophan residues has also been reported (Wendt et al, 2003;Suzuki et al, 2004;Sala et al, 2004). This protein modification reaction has been recently demonstrated for different proteins following reaction with peroxynitrite or a series of metalloproteins capable of peroxidase activity.…”

Section: Analysis Of Oxidatively/nitr(os)atively Products Of Tryptophmentioning

confidence: 81%

“…The occurrence of NO-Trp, 1-NO 2 -Trp, and 6-NO 2 -Trp has been demonstrated by detecting the corresponding adducts having a mass difference of +29 and +45 Da, respectively (Wendt et al, 2003;Suzuki et al, 2004;Sala et al, 2004). Under physiological conditions 6-NO 2 -Trp was stable, whereas NO-Trp, 1-NO 2 -Trp decomposed with half-lives of 1.5 and 18 hours, respectively.…”

Section: Analysis Of Oxidatively/nitr(os)atively Products Of Tryptophmentioning

confidence: 99%

Mass Spectrometry Approaches for the Molecular Characterization of Oxidatively/Nitrosatively Modified Proteins

Scaloni

2006

Redox Proteomics

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“…Among the various amino acids in proteins, tryptophan residues are especially susceptible to attack by reactive nitrogen species (48). Peroxynitrite is capable of oxidizing protein and non-protein sulfhydryl (-SH) groups including lipid peroxidation and reactivity with aromatic amino acid side chain in proteins to form nitroadducts (49).…”

Section: Cellular Biochemistry and Pathologymentioning

confidence: 99%

Contribution of Peroxynitrite, a Reactive Nitrogen Species, in the Pathogenesis of Autoimmunity

Ahmad¹,

Ahsan²

2011

Autoimmune Disorders - Pathogenetic Aspects

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Nitration and nitrosation of N-acetyl-l-tryptophan and tryptophan residues in proteins by various reactive nitrogen species

Cited by 90 publications

References 52 publications

The Reaction of Peroxynitrite with Morpholine (Secondary Amines) Revisited: The Overlooked Hydroxylamine Formation

The Reaction of Peroxynitrite with Morpholine (Secondary Amines) Revisited: The Overlooked Hydroxylamine Formation

Mass Spectrometry Approaches for the Molecular Characterization of Oxidatively/Nitrosatively Modified Proteins

Contribution of Peroxynitrite, a Reactive Nitrogen Species, in the Pathogenesis of Autoimmunity

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