38739-13-8

Basic information

• Product Name: 3-Bromo-L-tyrosine
• Synonyms: 3-Bromo-L-tyrosine;H-Tyr(3-Br)-OH;(S)-2-amino-3-(3-bromo-4-hydroxyphenyl)propanoic acid;L-3-Bromotyrosine
• CAS NO: 38739-13-8
• Molecular Formula: C₉H₁₀BrNO₃
• Molecular Weight: 260.0846
• Mol File: 38739-13-8.mol
• Article Data: 12

Chemical Properties

• Melting Point: 247-248 °C
• Boiling Point: 402.8±45.0 °C(Predicted)
• Appearance: /
• Density: 1.710±0.06 g/cm3(Predicted)
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: Aqueous Acid (Sparingly), DMSO (Heated), Methanol (Heated)
• PKA: 2.21±0.20(Predicted)
• CAS DataBase Reference: 3-Bromo-L-tyrosine(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Bromo-L-tyrosine(38739-13-8)
• EPA Substance Registry System: 3-Bromo-L-tyrosine(38739-13-8)

Safety Data

• Hazardous Substances Data: 38739-13-8(Hazardous Substances Data)

Usage

Description

3-Bromo-L-tyrosine is an amino acid derivative that features a bromine atom attached to the tyrosine molecule. This unique structure endows it with specific properties that make it valuable in various applications, particularly in the medical and pharmaceutical fields.

Uses

Used in Pharmaceutical Industry:
3-Bromo-L-tyrosine is used as a key component in the preparation and synthesis of polyclonal antibodies for combating brominated protein-related allergic responses and afflictions. Its presence in these antibodies helps target and neutralize allergens, providing relief to individuals suffering from such conditions.
Used in Medical Research:
In the field of medical research, 3-Bromo-L-tyrosine is utilized for its effectiveness in asthma control and prediction, particularly in children. Its role in these applications aids in the development of treatments and diagnostic tools to manage and prevent asthma episodes, ultimately improving the quality of life for affected individuals.

Upstream product

• 60-18-4 L-tyrosine 
• 64-18-6 formic acid 
• 7726-95-6 bromine 
• 95-56-7 2-hydroxybromobenzene 
• 113-24-6 sodium pyruvate 
• 108-86-1 bromobenzene 
• 127-17-3 2-oxo-propionic acid 
• 139517-74-1 methyl (S)-3 -(3-bromo-4-hydroxyphenyl)-2-((tert-butoxycarbonyl)amino)propanoate 
• 3417-91-2 L-tyrosine methyl ester HCl 
• 57-60-3 piruvate 

Downstream Products

• 108757-18-2 5-bromo-3-iodo-L-tyrosine 
• 98778-83-7 methyl (S)-2-amino-3-(3-bromo-4-hydroxyphenyl)propanoate hydrochloride 
• 113311-28-7 (S)-N-Boc-3-bromotyrosine 
• 109152-30-9 psammaplin A 
• 390424-25-6 3-(3-bromo-4-hydroxyphenyl)-2-oxopropionic acid 
• 390424-29-0 3-(3-bromo-4-hydroxy-phenyl)-2-tert-butoxycarbonylamino-propionic acid 2,5-dioxo-pyrrolidin-1-yl ester 
• 390424-30-3 Di-N-Boc-amino-psammaplin A 
• 98778-75-7 cyclo-3-bromo-L-tyrosyl-L-tyrosine 
• 98778-72-4 N-(tert-butoxycarbonyl)-L-tyrosyl-3-bromo-L-tyrosine methyl ester 

Relevant articles and documents

A Single Atom Change Facilitates the Membrane Transport of Green Fluorescent Proteins in Mammalian Cells

Direct delivery of proteins into mammalian cells is a challenging problem in biological and biomedical applications. The most common strategies for the delivery of proteins into the cells include the use of cell-penetrating peptides or supercharged proteins. Herein, we show for the first time that a single atom change, hydrogen to halogen, at one of the tyrosine residues can increase the cellular entry of ～28 kDa green fluorescent protein (GFP) in mammalian cells. The protein uptake is facilitated by a receptor-mediated endocytosis and the cargo can be released effectively into cytosol by co-treatment with the endosomolytic peptide ppTG21.

Synthesis and trypanocide activity of chloro-l-tyrosine and bromo-l-tyrosine derivatives

Twenty-two halogenated l-tyrosine derivatives were synthesized to examine new substances for the treatment of Chagas disease. The synthesis of these derivatives with different degree of substitution in the amino group with methyl iodide, giving primary, tertiary, and quaternary amino acids. All compounds were tested in vitro against intracellular amastigotes of Trypanosoma cruzi, and the cytotoxicity were evaluated over monocytic cell line U-937. Compound 25 was the most active against T. cruzi with a EC50 of 75.52 μM compared with benznidazole with a EC50 of 58.79 μM. Compounds 3, 4, 7, and 15 were the derivatives with the best selectivity index (SI) with values of 7.5, 8.3,12.1, and 8.6, respectively. Finally, compound 7 was the safer and the more promising derivative against T. cruzi.

Biocatalytic One-Pot Synthesis of l-Tyrosine Derivatives from Monosubstituted Benzenes, Pyruvate, and Ammonia

l-Tyrosine derivatives were obtained in >97% ee via a biocatalytic one-pot two-step cascade using substituted benzenes, pyruvate, and NH3 as starting materials. In the first step, monosubstituted arenes were regioselectively hydroxylated in the o-position by monooxygenase P450 BM3 (using O2 as oxidant with NADPH-recycling) to yield the corresponding phenols, which subsequently underwent C-C coupling and simultaneous asymmetric amination with pyruvate and NH3 using tyrosine phenol lyase to furnish l-DOPA surrogates in up to 5.2 g L-1. Instead of analytically pure arenes, crude aromatic gasoline blends containing toluene were used to yield 3-methyl-l-tyrosine in excellent yield (2 g L-1) and >97% ee.