3604-79-3

Basic information

• Product Name: (2S)-2-amino-3-(4-hydroxy-3-nitro-phenyl)propanoic acid
• Synonyms: (2S)-2-amino-3-(4-hydroxy-3-nitro-phenyl)propanoic acid;3-Mononitrotyrosine;Tyrosine, 3-nitro-;DL-Tyrosine, 3-nitro-;2-AMino-3-(4-hydroxy-3-nitrophenyl)propanoic acid
• CAS NO: 3604-79-3
• Molecular Formula: C₉H₁₀N₂O₅
• Molecular Weight: 226.19
• Mol File: 3604-79-3.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 431.6°Cat760mmHg
• Flash Point: 214.8°C
• Appearance: /
• Density: 1.531g/cm³
• Storage Temp.: 2-8°C
• CAS DataBase Reference: (2S)-2-amino-3-(4-hydroxy-3-nitro-phenyl)propanoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (2S)-2-amino-3-(4-hydroxy-3-nitro-phenyl)propanoic acid(3604-79-3)
• EPA Substance Registry System: (2S)-2-amino-3-(4-hydroxy-3-nitro-phenyl)propanoic acid(3604-79-3)

Safety Data

• Hazardous Substances Data: 3604-79-3(Hazardous Substances Data)

Usage

Description

(2S)-2-amino-3-(4-hydroxy-3-nitro-phenyl)propanoic acid, also known as 3-nitrotyrosine, is a non-natural amino acid derived from L-tyrosine with a nitro group at the 3-position on the phenyl ring. It is a chiral molecule with the S-configuration and has been found to play a role in various biological processes and pathological conditions.

Uses

Used in Pharmaceutical Industry:
(2S)-2-amino-3-(4-hydroxy-3-nitro-phenyl)propanoic acid is used as a therapeutic agent for treating conditions related to oxidative stress and inflammation. Its presence in biological systems is associated with the nitration of tyrosine residues in proteins, which can modulate protein function and contribute to the pathogenesis of various diseases, including neurodegenerative disorders and cardiovascular diseases.
Used in Research and Development:
In the field of research, (2S)-2-amino-3-(4-hydroxy-3-nitro-phenyl)propanoic acid serves as a valuable compound for studying the effects of nitrosative and oxidative stress on cellular processes. It can be used as a molecular probe to investigate the role of nitrotyrosine in protein function and the mechanisms underlying nitration-mediated cellular responses.
Used in Drug Delivery Systems:
Similar to gallotannin, (2S)-2-amino-3-(4-hydroxy-3-nitro-phenyl)propanoic acid can be incorporated into drug delivery systems to enhance its bioavailability and therapeutic efficacy. These systems can be designed to target specific tissues or cells, allowing for more precise and effective treatment of diseases associated with nitrosative and oxidative stress.
Used in Analytical Chemistry:
(2S)-2-amino-3-(4-hydroxy-3-nitro-phenyl)propanoic acid can be employed as a chiral reference compound in the development and validation of analytical methods for the detection and quantification of nitrotyrosine in biological samples. This can be particularly useful in the study of oxidative stress-related conditions and the assessment of the effects of potential therapeutic interventions.

Upstream product

• 556-02-5 ?Tyr 

Downstream Products

• 5575-03-1 (2S)-2-tert-butoxycarbonylamino-3-(4-hydroxy-3-nitro-phenyl)-propionic acid 
• 3387-86-8 3-amino-tyrosine 
• 3078-39-5 3-iodo-DL-tyrosine 

Relevant articles and documents

Interference of the polyphenol epicatechin with the biological chemistry of nitric oxide- and peroxynitrite-mediated reactions

The formation of reactive nitrogen species in mammalians has both beneficial and undesirable effects. Nitric oxide (NO) production in endothelial cells leads to vascular smooth muscle relaxation, but if reactive nitrogen species are generated in high amounts by cells under inflammatory conditions they are toxic. Flavonoids like (-)-epicatechin show an inverse association of their intake with diseases thought to be associated with overproduction of reactive nitrogen species. We found that the formation of cyclic GMP in cultured porcine aortic endothelial cells was not affected by up to 1mM (-)-epicatechin. Half maximal inhibition of interferon-γ/ lipopolysaccharide induced nitrite accumulation in murine macrophages required about 0.5mM of the flavonoid. In contrast, nitration of free tyrosine triggered by 0.1 and 1mM authentic peroxynitrite was inhibited by (-)-epicatechin with IC50 values of 6.6 and 28.0μM, respectively. The presence of 15mM sodium bicarbonate had no significant effect. Nitration of protein-bound tyrosine in phorbol 12-myristate 13-acetate treated HL-60 cells in the presence of nitrite was inhibited by (-)-epicatechin at a similar concentration range (IC50=10-100μM). Myeloperoxidase activity of phorbol 12-myristate 13-acetate stimulated HL-60 cells was inhibited by (-)-epicatechin with an IC50 value of 77.4μM. Epicatechin inhibited dihydrorhodamine oxidation by 50μM authentic peroxynitrite and 1mM 3-morpholino-sydnonimine with IC50 values of 11.8 and 0.63μM, respectively. Our data suggest that at up to 0.1mM (-)-epicatechin preferentially inhibits NO-related nitration and oxidation reactions without affecting NO synthesis and cyclic GMP signaling.

NOVEL MULTIMERIC CD40 LIGANDS, METHOD FOR PREPARING SAME AND USE THEREOF FOR PREPARING DRUGS

The invention concerns a compound of formula (I), wherein Y represents a macrocycle whereof the cycle comprises 9 to 36 atoms, and is functionalized by three amine or COOH functions; Rc represents a group of formula H—Xa—Xb—Xc—Xd—Xe—(Xf)i—, wherein i represents 0 or 1, Xn is in particular selected among lysine, arginine, ornithine residues, Xb is in particular selected among glycine, asparagine, L-proline or D-proline residues, Xc et Xd are in particular selected among tyrosine, phenylalanine or 3-nitrotyrosine residues, Xe et Xf are in particular selected among the following amino acid residues: NH2—(CH2)n—COOH, n ranging from 1 to 10 or NH2—(CH2—CH2—O)m—CH2CH2COOH, m ranging from 3 to 6, provided that one at least of the amino acid residues Xa, Xb, Xc and Xd is different from the corresponding amino acid in the sequence of the natural CD40 143Lys-Gly-Tyr-Tyr146 fragment

Metalloporphyrin treatment of neurologic disease

The present invention provides a method of treating amyotrophic lateral sclerosis and other neurologic diseases by administering a compound of the formula where R is selected from the group consisting of (C6H4)CO2H, (Csub