3604-79-3

Usage

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

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

Relevant academic research and scientific papers

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 MOLECULES, A PROCESS FOR PREPARING THE SAME AND THE USE THEREOF FOR MANUFACTURING MEDICINAL DRUGS

The invention relates to a compound of the formula (I): in which k and j are independently 0 or 1, Y is a macrocycle in which the cycle includes 9 to 36 carbon atoms and is functionalised by three amino functions and by a chain for attaching the spacer arm Z via an X bond, Rc is a binding pattern with a receptor of the TNF superfamily, X is a chemical function for binding the Y group to the space arm, and Z is a bi-, tri- or tetra-functional spacer arm.

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

Processes for conversion of tyrosine to p-hydroxystyrene and p-acetoxystyrene

Tyrosine was converted to p-hydroxystyrene in a two-step reaction without purification of individual intermediates. Conditions were determined for bromination of tyrosine in which reactive intermediates were formed. The mixture of these intermediates was used directly in a second step reaction to produce p-hydroxystyrene. The p-hydroxystyrene was further acetylated to produce p-acetoxystyrene in the second step reaction vessel.

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

The reaction of peroxynitrite with organic molecules bearing a biologically important functionality. The multiplicity of reaction modes as exemplified by hydroxylation, nitration, nitrosation, dealkylation, oxygenation, and oxidative dimerization and cleavage

The reactions of peroxynitrite with a variety of organic molecules which include a biologically important functionality have been examined to construct a simple model for the peroxynitrite-induced in vivo transformations as well as a chemical probe for the active species involved therein. Phenols were found to undergo hydroxylation, nitration, oxidative dimerization, and oxidation to cyclohexadienones and quinones. The ring nitration of catechol was confirmed for the first time in the in vitro reaction of peroxynitrite. Dealkylation and N-oxide formation were the major reaction modes observed for N,N-dimethyl-p-toluidine. 1,2-Phenylenediamine gave benzotriazole in high yield. The electron-deficient C-C double bond in 1,4-naphthoquinone underwent epoxidation, while the electron-rich C-C double bond in α-methylstyrene suffered oxidative cleavage to acetophenone. The activated double bond in trans-stilbene underwent oxidative cleavage and epoxidation in parallel to give benzaldehyde and trans-stilbene oxide as the major products. The triple bond in diphenylacetylene was simply oxygenated to form benzil, together with trace amounts of ring nitration products. 1-Phenylethanol, imidazole, 2′-deoxyadenosine, and 2′-deoxyguanosine were all quite slow to react, while uracil and cytosine were almost inert to peroxynitrite. The reaction modes exhibited by peroxynitrite are too widespread and complicated to explain the whole mechanistic pathway in terms of a single active species. All reaction modes observed for the peroxynitrite to date could be classified into five categories according to their types: i) electron transfer type, ii) O-electrophilic type, iii) N-electrophilic type, iv) O-nucleophilic type, and v) radical type. Some of these may compete under certain conditions. The active species involved in each of these types of reactions are as follows: i) NO+, NO2, and OH, ii) ONOOH, iii) ONOOH and NO+, iv) OOH- and ONOO-, and v) NO2 and OH.

A study of the reaction of different phenol substrates with nitric oxide and peroxynitrite

The reactivity of different phenol substrates with nitric oxide and peroxynitrite was investigated. In general, nitration is the major reaction with peroxynitrite, while reactions with aqueous solutions of nitric oxide led to mixtures of nitro and nitroso derivatives depending upon the phenol. Nitrosation occurs on phenol substrates bearing a free para- position with respect to the OH group with the exception of 1-naphthol, which afforded a 1:1 mixture of the 2- and the 4-nitroso derivatives. Chromans 7 and 8 showed the highest reactivity with peroxynitrite, which suggests that they can act as efficient scavengers of this toxic intermediate. In both cases the corresponding 5-nitro derivative was the only reaction product detected. Finally, the fact that chroman 8 reacts with nitric oxide to afford the p- quinone derivative 22a in 90% yield suggests that this antioxidant could also be of potential use as specific nitric oxide tracer in biological tissues.