Nitrotyrosine

Nitrotyrosine[1]
IUPAC name (2S)-2-Amino-3-(4-hydroxy-3-nitrophenyl)propanoic acid
Other names 3-Nitro-L-tyrosine; 3-Nitrotyrosine
Identifiers
CAS number	621-44-3
PubChem	65124
ChemSpider	58633 Y
DrugBank	DB03867
ChEBI	CHEBI:44454 Y
Jmol-3D images	Image 1
SMILES O=[N+]([O-])c1cc(ccc1O)C[C@@H](C(=O)O)N
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 Y Key: FBTSQILOGYXGMD-LURJTMIESA-N Y InChI=1/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 Key: FBTSQILOGYXGMD-LURJTMIEBK
Properties
Molecular formula	C9H10N2O5
Molar mass	226.19 g/mol
Appearance	Yellow to green crystalline solid
Melting point	233-235 °C (dec.)
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Nitrotyrosine is a product of tyrosine nitration mediated by reactive nitrogen species such as peroxynitrite anion and nitrogen dioxide. It is detected in large number of pathological conditions^[2][3] and is considered a marker of NO-dependent, reactive nitrogen species-induced nitrative stress. Nitrotyrosine is found in numerous disease-affected tissues, such as the cornea in keratoconus.^[4] Peroxynitrite and/or nitrative stress may participate in the pathogenesis of diabetes^[5]

References

1. ^ 3-Nitro-L-tyrosine at Sigma-Aldrich
2. ^ Mohiuddin I, Chai H, Lin PH, Lumsden AB, Yao Q, Chen C (June 2006). "Nitrotyrosine and chlorotyrosine: clinical significance and biological functions in the vascular system". J. Surg. Res. 133 (2): 143–9. doi:10.1016/j.jss.2005.10.008. PMID 16360172. http://linkinghub.elsevier.com/retrieve/pii/S0022-4804(05)00544-5. 
3. ^ Pacher P, Beckman JS, Liaudet L (2007). "Nitric oxide and peroxynitrite in health and disease.". Physiol Rev. 87 (1): 315. doi:10.1152/physrev.00029.2006. PMC 2248324. PMID 17237348. http://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=2248324. 
4. ^ Buddi R, Lin B, Atilano SR, Zorapapel NC, Kenney MC, Brown DJ (March 2002). "Evidence of oxidative stress in human corneal diseases". J. Histochem. Cytochem. 50 (3): 341–51. PMID 11850437. http://www.jhc.org/cgi/pmidlookup?view=long&pmid=11850437. 
5. ^ Pacher P, Obrosova IG, Mabley JG, Szabó C (2005). "Role of nitrosative stress and peroxynitrite in the pathogenesis of diabetic complications. Emerging new therapeutical strategies". Curr. Med. Chem. 12 (3): 267–75. PMC 2225483. PMID 15723618. http://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=2225483.