3-Nitro-L-tyrosine

Base Information

• Chemical Name: 3-Nitro-L-tyrosine
• CAS No.: 621-44-3
• Molecular Formula: C9H10N2O5
• Molecular Weight: 226.189
• Hs Code.: 29225090
• European Community (EC) Number: 210-688-6
• UNII: 7COY1HA6HK
• DSSTox Substance ID: DTXSID80863216
• Nikkaji Number: J78G
• Wikidata: Q412383
• NCI Thesaurus Code: C126911
• Metabolomics Workbench ID: 37922
• ChEMBL ID: CHEMBL1234745
• Mol file: 621-44-3.mol

Synonyms:3-mononitrotyrosine;3-nitro-L-tyrosine;3-nitrotyrosine;3-nitrotyrosine, (DL)-isomer;3-nitrotyrosine, (L)-isomer;nitrotyrosine

Chemical Property of 3-Nitro-L-tyrosine

Chemical Property:

• Appearance/Colour: ochre-yellow to yellow-green powder
• Vapor Pressure: 3.24E-08mmHg at 25°C
• Melting Point: 233-235 °C (dec.)(lit.)
• Refractive Index: 1.5373 (estimate)
• Boiling Point: 431.6 °C at 760 mmHg
• PKA: 2.17±0.20(Predicted)
• Flash Point: 214.8 °C
• PSA: 129.37000
• Density: 1.531 g/cm³
• LogP: 1.47830
• Storage Temp.: -15°C
• Solubility.: Aqueous Acid (Slightly), Water
• Water Solubility.: insoluble
• XLogP3: -2
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 3
• Exact Mass: 226.05897142
• Heavy Atom Count: 16
• Complexity: 278

Purity/Quality:

98%,99%, ^*data from raw suppliers

Nitrotyrosine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 24/25-37/39-26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=C(C=C1CC(C(=O)O)N)[N+](=O)[O-])O
• Isomeric SMILES: C1=CC(=C(C=C1C[C@@H](C(=O)O)N)[N+](=O)[O-])O
• 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.
• Uses: A marker for peroxynitrite. Oxidant and cytotoxic agent. 3-Nitro-L-tyrosine is used as an indicator of the formation of peroxynitrite by NO-dependent oxidative damage.

Technology Process of 3-Nitro-L-tyrosine

There total 11 articles about 3-Nitro-L-tyrosine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 45.0%

L-tyrosine (60-18-4,18875-48-4,25619-78-7,30704-25-7) → 3-nitro-L-tyrosine (621-44-3)

Guidance literature:

With diethylenetriaminopentaacetic acid; dihydrogen peroxide; Nitrite; peroxidase; In aq. phosphate buffer; at 20 ℃; pH=6; Reagent/catalyst; Kinetics; Enzymatic reaction;

DOI:10.1016/j.bbagen.2019.07.012

Reference yield:

L-tyrosine (60-18-4,18875-48-4,25619-78-7,30704-25-7) → (S)-2-[(S)-2-Amino-3-(4-hydroxy-phenyl)-propionylamino]-3-(4-hydroxy-phenyl)-propionic acid (1050-28-8) + 3-nitro-L-tyrosine (621-44-3)

Guidance literature:

With dihydrogen peroxide; copper(II) sulfate; In aq. phosphate buffer; at 45 ℃; for 2h; pH=7.4; Sealed tube;

DOI:10.1021/acs.jafc.0c03926

Reference yield:

(S)-3-(4-hydroxy-3-nitrophenyl)-2-[(ethoxycarbonyl)amino]-1-propanoic acid methyl ester (726181-69-7) → 3-nitro-L-tyrosine (621-44-3)

Guidance literature:

With potassium hydroxide;

DOI:10.1016/j.bmcl.2004.03.103

upstream raw materials:

L-tyrosine

nitric acid

(S)-3-(4-hydroxy-3-nitrophenyl)-2-[(ethoxycarbonyl)amino]-1-propanoic acid methyl ester

L-Tyr-OMe

Downstream raw materials:

(2S)-3-(4-hydroxy-3-nitrophenyl)-2-{[(4-methylphenyl)sulfonyl]amino} propanoic acid

levodopa

(S)-2-Hydroxy-3-(4-hydroxy-3-nitrophenyl)-propanoic acid

methyl 3-nitro-L-tyrosinate

Refernces

• 1、 Nakagawa, Hidehiko,Takusagawa, Mitsuko,Arima, Hiromi,Furukawa, Kumiko,Kinoshita, Takeshi,Ozawa, Toshihiko,Ikota, Nobuo. "Selective scavenging property of the indole moiety for the nitrating species of peroxynitrite". . p. 146 - 149. Retrieved 2004.
• 2、 Hodges, George R.,Marwaha, Jasvir,Paul, Thomas,Ingold. "A novel procedure for generating both nitric oxide and superoxide in situ from chemical sources at any chosen mole ratio. First application: Tyrosine oxidation and a comparison with preformed peroxynitrite". . p. 1287 - 1293. Retrieved 2000.
• 3、 Lehnig, Manfred,Kirsch, Michael. "15N CIDNP investigations of the peroxynitric acid nitration of l-tyrosine and of related compounds". . p. 721 - 729. Retrieved 2006.
• 4、 Sanchez-Cruz, Pedro,Alegria, Antonio E.. "Photosensitized production of nitric oxide and peroxynitrite from a carbon-bound diazenium diolate and 2-methyl-2-nitrosopropane". . p. 79 - 85. Retrieved 2016.
• 5、 Tomita, Hiroya,Katsuyama, Yohei,Minami, Hiromichi,Ohnishi, Yasuo. "Identification and characterization of a bacterial cytochrome P450 monooxygenase catalyzing the 3-nitration of tyrosine in rufomycin biosynthesis". . p. 15859 - 15869. Retrieved 2017.
• 6、 Maimon, Eric,Samuni, Amram,Goldstein, Sara. "Mechanistic insight into the catalytic inhibition by nitroxides of tyrosine oxidation and nitration". . . Retrieved 2019.
• 7、 Shim, Eric Kian-Shiun,Lee, Soo-Ying. "Nitration of Tyrosine in the Mucin Glycoprotein of Edible Bird's Nest Changes Its Color from White to Red". . p. 5654 - 5662. Retrieved 2018/05/30.