Nitrotyrosine

Structural formula
General
Surname	Nitrotyrosine
other names	(2 S ) -2-Amino-3- (4-hydroxy-3-nitrophenyl) propanoic acid ( IUPAC ) ; L - (-) - nitrotyrosine; ( S ) - (-) - nitrotyrosine; D - (+) - nitrotyrosine; ( R ) - (+) - nitrotyrosine; 3-nitro- L- tyrosine;
Molecular formula	C 9 H 10 N 2 O 5
Brief description	yellow-greenish solid
External identifiers / databases
EC number	210-688-6
ECHA InfoCard	100.009.718
PubChem	65124
ChemSpider	58633
DrugBank	DB03867
Wikidata	Q412383
properties
Molar mass	226.19 g mol −1
Physical state	firmly
Melting point	233–235 ° C (decomposition)
solubility	almost insoluble in water
safety instructions
GHS labeling of hazardous substances	no GHS pictograms
	no GHS pictograms
H and P phrases	H: no H-phrases
	P: no P-phrases
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Nitrotyrosine , more correctly 3-nitrotyrosine , is a non-proteinogenic amino acid . The compound is created in organisms by the action of the reactive nitrogen species peroxynitrite on tyrosine .

properties

3-nitrotyrosine is a derivative of the proteinogenic amino acid tyrosine. It is a yellowish to slightly greenish solid with a decomposition point at around 235 ° C.

Occurrence and origin

Of the two possible enantiomers of chiral 3-nitrotyrosine, only the L form occurs in organisms . There it is formed from the proteinogenic amino acid tyrosine under the action of the peroxynitrite anion ( nucleophilic aromatic substitution ).

Biomarkers

3-nitro- L- tyrosine is used in laboratory diagnostics as a biomarker for nitrosative stress . The level of 3-nitro- L- tyrosine in the blood serum is increased in a number of diseases such as gastric cancer , arteriosclerosis , lung diseases (such as asthma), sepsis , vasculitis and other inflammatory diseases . In general, the compound is a biomarker for apoptosis (programmed cell death).

The detection of 3-nitro- L- tyrosine can take place , for example, via HPLC-MS .

Individual evidence

↑ ^a ^b ^c data sheet 3-Nitro-L-tyrosine from Sigma-Aldrich , accessed on May 7, 2017 ( PDF ).
^ Entry on 3-Nitro-L-tyrosine at ChemicalBook , accessed on January 6, 2010.
↑ C. Oldreive, C. Rice-Evans: "The mechanisms for nitration and nitrotyrosine formation in vitro and in vivo: impact of diet", in: Free Radic. Res. , 2001 , 35 , pp. 215-231; PMID 11697121 .
↑ SA Kharitonov, PJ Barnes: "Nitric oxide, nitrotyrosine, and nitric oxide modulators in asthma and chronic obstructive pulmonary disease", in: Curr Allergy Asthma Rep , 2003 , 3 , pp. 121-129; PMID 12562551 .
^ I. Mohiuddin, H. Chai, PH Lin, AB Lumsden, Q. Yao, C. Chen: "Nitrotyrosine and chlorotyrosine: clinical significance and biological functions in the vascular system", in: Journal of Surgical Research , 2006 , 133 , Pp. 143-149; PMID 16360172 .
↑ AW Abu-Qare, MB Abou-Donia: "Biomarkers of apoptosis: release of cytochrome c, activation of caspase-3, induction of 8-hydroxy-2'-deoxyguanosine, increased 3-nitrotyrosine, and alteration of p53 gene", in: J Toxicol Env Health Pt B-Crit Rev , 2001 , 4 , pp. 313-332, PMID 11503418 .
↑ H. Ryberg and K. Caidahl: "Chromatographic and mass spectrometric methods for quantitative determination of 3-nitrotyrosine in biological samples and their application to human samples", in: J. Chromatogr. B , 2007 , 851 , pp. 160-171, PMID 17344105 .

literature

P. Pacher, IG Obrosova, JG Mabley, C. Szabo: “Role of nitrosative stress and peroxynitrite in the pathogenesis of diabetic complications. Emerging new therapeutic strategies ”, in: Curr Med Chem , 2005 , 12 , pp. 267-275; PMID 15723618 ; PMC 2225483 (free full text).
R. Buddi, B. Lin, SR Atilano, NC Zorapapel, MC Kenney, DJ Brown: "Evidence of oxidative stress in human corneal diseases" , in: J Histochem Cytochem , 2002 , 50 , pp. 341-351; PMID 11850437
KA Hanafy, JS Krumenacker, F. Murad: “NO, nitrotyrosine, and cyclic GMP in signal transduction”, in: Med Sci Monit , 2001 , 7 , pp. 801-819; PMID 11433215 .
H. Nakazawa, N. Fukuyama, S. Takizawa, C. Tsuji, M. Yoshitake, H. Ishida: "Nitrotyrosine formation and its role in various pathological conditions", in: Free Radic. Res. , 2000 , 33 , pp. 771-784; PMID 11237099 .
A. Ceriello: "Nitrotyrosine: new findings as a marker of postprandial oxidative stress", in: Int. J. Clin. Pract. Suppl. , 2002 , 129 , pp. 51-58; PMID 12166608 .
MW Duncan: “A review of approaches to the analysis of 3-nitrotyrosine”, in: Amino Acids , 2003 , 25 , pp. 351-361; PMID 14661096 .
D. Tsikas, K. Caidahl: "Recent methodological advances in the mass spectrometric analysis of free and protein-associated 3-nitrotyrosine in human plasma", in: J. Chromatogr. B, analyte. Technol. Biomed. Life Sci. , 2005 , 814 , pp. 1-9; PMID 15607702 .

[sigma-1] ta sheet 3-Nitro-L-tyrosine from Sigma-Aldrich , accessed on May 7, 2017 ( PDF ).

[chemicalbook-2] Entry on 3-Nitro-L-tyrosine at ChemicalBook , accessed on January 6, 2010.

[3] C. Oldreive, C. Rice-Evans: "The mechanisms for nitration and nitrotyrosine formation in vitro and in vivo: impact of diet", in: Free Radic. Res. , 2001 , 35 , pp. 215-231; PMID 11697121 .

[4] SA Kharitonov, PJ Barnes: "Nitric oxide, nitrotyrosine, and nitric oxide modulators in asthma and chronic obstructive pulmonary disease", in: Curr Allergy Asthma Rep , 2003 , 3 , pp. 121-129; PMID 12562551 .

[5] I. Mohiuddin, H. Chai, PH Lin, AB Lumsden, Q. Yao, C. Chen: "Nitrotyrosine and chlorotyrosine: clinical significance and biological functions in the vascular system", in: Journal of Surgical Research , 2006 , 133 , Pp. 143-149; PMID 16360172 .

[6] AW Abu-Qare, MB Abou-Donia: "Biomarkers of apoptosis: release of cytochrome c, activation of caspase-3, induction of 8-hydroxy-2'-deoxyguanosine, increased 3-nitrotyrosine, and alteration of p53 gene", in: J Toxicol Env Health Pt B-Crit Rev , 2001 , 4 , pp. 313-332, PMID 11503418 .

[7] H. Ryberg and K. Caidahl: "Chromatographic and mass spectrometric methods for quantitative determination of 3-nitrotyrosine in biological samples and their application to human samples", in: J. Chromatogr. B , 2007 , 851 , pp. 160-171, PMID 17344105 .