3-Nitro-L-tyrosine Chemical Properties

Melting point:

233-235 °C (dec.) (lit.)

alpha 

4 º (c=1, 1N HCl)

Boiling point:

367.79°C (rough estimate)

Density 

1.4160 (rough estimate)

refractive index 

1.5373 (estimate)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

solubility 

Aqueous Acid (Slightly), Water

pka

2.17±0.20(Predicted)

form 

crystalline

color 

yellow to green

Water Solubility 

insoluble

BRN 

2813157

InChI

InChI=1S/C9H10N2O5/c10-6(9(13)14)3-5-1-2-8(12)7(4-5)11(15)16/h1-2,4,6,12H,3,10H2,(H,13,14)/t6-/m0/s1

InChIKey

FBTSQILOGYXGMD-LURJTMIESA-N

SMILES

C(O)(=O)[C@H](CC1=CC=C(O)C([N+]([O-])=O)=C1)N

CAS DataBase Reference

621-44-3(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

24/25-37/39-26-36

WGK Germany 

3

HS Code 

29225090

MSDS

• Language:English Provider:3-Nitro-L-tyrosine
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

3-Nitro-L-tyrosine Usage And Synthesis

Description

Nitrotyrosine is formed by peroxynitrite-mediated nitration of protein tyrosine residues. Its presence on proteins can be used as a marker for peroxynitrite formation in vivo. Both free and protein-bound nitrotyrosine are commonly found in mammalian tissues and are increased in pathological conditions. The basal levels of free nitrotyrosine in human plasma is approximately 3 nM as determined by gas chromatography/mass spectrometry.

Chemical Properties

ochre-yellow to yellow-green powder

Uses

A marker for peroxynitrite. Oxidant and cytotoxic agent.

Uses

3-Nitro-L-tyrosine is used as an indicator of the formation of peroxynitrite by NO-dependent oxidative damage.

Definition

ChEBI: 3-nitro-L-tyrosine is a 3-nitrotyrosine comprising L-tyrosine having a nitro group at the 3-position on the phenyl ring. It is a L-tyrosine derivative, a non-proteinogenic L-alpha-amino acid and a 3-nitrotyrosine. It is an enantiomer of a 3-nitro-D-tyrosine.

Biochem/physiol Actions

Oxidant and cytotoxic agent.

References

[1] J S BECKMAN  W H K. Nitric oxide, superoxide, and peroxynitrite: the good, the bad, and ugly.[J]. American Journal of Physiology, 1996, 271 5 Pt 1: C1424-37. DOI: 10.1152/ajpcell.1996.271.5.c1424
[2] J S BECKMANN. Extensive nitration of protein tyrosines in human atherosclerosis detected by immunohistochemistry.[J]. Biological chemistry Hoppe-Seyler, 1994, 375 2: 81-88. DOI: 10.1515/bchm3.1994.375.2.81
[3] K ABE. Upregulation of protein-tyrosine nitration in the anterior horn cells of amyotrophic lateral sclerosis.[J]. Neurological Research, 1997, 19 2: 124-128. DOI: 10.1080/01616412.1997.11740784
[4] ROBERT J. FERRANTE PHD.  Leslie A S PhD, MD. Increased 3-nitrotyrosine and oxidative damage in mice with a human copper/zinc superoxide dismutase mutation[J]. Annals of Neurology, 2004, 42 3: 326-334. DOI: 10.1002/ana.410420309
[5] I Y HADDAD. Quantitation of nitrotyrosine levels in lung sections of patients and animals with acute lung injury.[J]. Journal of Clinical Investigation, 1994, 94 6: 2407-2413. DOI: 10.1172/jci117607
[6] M. OHYA. Plasma Nitrotyrosine Concentration Relates to Prognosis in Human Septic Shock[J]. SHOCK, 2002, 18 1: 116-118. DOI: 10.1097/00024382-200208000-00004
[7] DIMITRIOS TSIKAS. Accurate quantification of basal plasma levels of 3-nitrotyrosine and 3-nitrotyrosinoalbumin by gas chromatography–tandem mass spectrometry[J]. Journal of Chromatography B, 2003, 784 1: Pages 77-90. DOI: 10.1016/s1570-0232(02)00751-1
[8] EDZARD SCHWEDHELM. Gas Chromatographic–Tandem Mass Spectrometric Quantification of Free 3-Nitrotyrosine in Human Plasma at the Basal State[J]. Analytical biochemistry, 1999, 276 2: Pages 195-203. DOI: 10.1006/abio.1999.4361
[9] JIAN LIU  Steven G L. High-fat, low-carbohydrate diet alters myocardial oxidative stress and impairs recovery of cardiac function after ischemia and reperfusion in obese rats[J]. Nutrition Research, 2013, 33 4: Pages 311-321. DOI: 10.1016/j.nutres.2013.02.005

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