42538-40-9

Basic information

• Product Name: L-2-Bromophenylalanine
• Synonyms: L-2-BROMOPHENYLALANINE;H-O-BROMO-L-PHE-OH;H-PHE(2-BR)-OH;2-BROMO-L-PHENYLALANINE;(2S)-2-amino-3-(2-bromophenyl)propanoic acid;L-2-Br-Phe-OH;(S)-2-Amino-3-(2'-bromophenyl)propanoic acid;L-2-Bromo-phe-OH
• CAS NO: 42538-40-9
• Molecular Formula: C₉H₁₀BrNO₂
• Molecular Weight: 244.09
• Product Categories: Amino Acids;Phenylalanine analogs and other aromatic alpha amino acids;Amino Acid Derivatives;Chiral Reagent;a-amino
• Mol File: 42538-40-9.mol

Chemical Properties

• Melting Point: 270°C (dec.)
• Boiling Point: 363.188 °C at 760 mmHg
• Flash Point: 173.45 °C
• Appearance: Off-white/Powder
• Density: 1.589 g/cm³
• Storage Temp.: Store at -15°C
• PKA: 2.16±0.10(Predicted)
• CAS DataBase Reference: L-2-Bromophenylalanine(CAS DataBase Reference)
• NIST Chemistry Reference: L-2-Bromophenylalanine(42538-40-9)
• EPA Substance Registry System: L-2-Bromophenylalanine(42538-40-9)

Safety Data

• Hazard Codes: Xi
• Safety Statements: 24/25
• Hazardous Substances Data: 42538-40-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
L-2-Bromophenylalanine is used as a building block for drug development due to its ability to improve the stability and bioactivity of peptides, which can lead to the creation of more effective therapeutic agents.
Used in Research and Development:
L-2-Bromophenylalanine is used as a key component in the synthesis of peptides and proteins, facilitating research in various biological and medical fields.
Used in Neurological Disorder Treatment:
L-2-Bromophenylalanine is studied for its potential therapeutic applications in the treatment of neurological disorders, offering a new avenue for developing treatments for such conditions.
Used in Radiolabeled Imaging Agents:
L-2-Bromophenylalanine serves as a precursor for radiolabeled imaging agents, contributing to advancements in diagnostic imaging techniques in medicine.
Used in Medicinal Chemistry and Drug Discovery:
L-2-Bromophenylalanine is utilized in the field of medicinal chemistry and drug discovery, where its unique properties can be harnessed to develop novel compounds with potential therapeutic applications.

Upstream product

• 1991-79-3 2-amino-3-(2-bromophenyl)propanoic acid 
• 6630-33-7 ortho-bromobenzaldehyde 
• 120240-65-5 3-(2-bromophenyl)-2-oxopropanoic acid 
• 3060-50-2 2,2-diphenylglycine 
• 7345-79-1 2-bromocinnamic acid 
• 7345-79-1 2-bromocinnamic acid 
• 63-91-2 L-phenylalanine 

Downstream Products

• 147912-84-3 (S)-N-(9-phenylfluoren-9-yl)-o-bromophenylalanine 
• 1270295-82-3 Z-L-Phe(2Br) 
• 458528-69-3 (S)-3-(2-bromophenyl)-2-hydroxypropionic acid 
• 79815-20-6 (S)-indoline-2-carboxylic acid 
• 612548-09-1 (2S)-3-(2-bromo-phenyl)-2-methoxycarbonylamino-propionic acid 
• 6960-35-6 (S)-O-phenylphenylalanine 
• 938069-18-2 2-bromo-L-phenylalanine methyl ester 

Relevant articles and documents

A novel phenylalanine ammonia-lyase from Pseudozyma antarctica for stereoselective biotransformations of unnatural amino acids

A novel phenylalanine ammonia-lyase of the psychrophilic yeast Pseudozyma antarctica (PzaPAL) was identified by screening microbial genomes against known PAL sequences. PzaPAL has a significantly different substrate binding pocket with an extended loop (26 aa long) connected to the aromatic ring binding region of the active site as compared to the known PALs from eukaryotes. The general properties of recombinant PzaPAL expressed in E. coli were characterized including kinetic features of this novel PAL with L-phenylalanine (S)-1a and further racemic substituted phenylalanines rac-1b-g,k. In most cases, PzaPAL revealed significantly higher turnover numbers than the PAL from Petroselinum crispum (PcPAL). Finally, the biocatalytic performance of PzaPAL and PcPAL was compared in the kinetic resolutions of racemic phenylalanine derivatives (rac-1a-s) by enzymatic ammonia elimination and also in the enantiotope selective ammonia addition reactions to cinnamic acid derivatives (2a-s). The enantiotope selectivity of PzaPAL with o-, m-, p-fluoro-, o-, p-chloro- and o-, m-bromo-substituted cinnamic acids proved to be higher than that of PcPAL.

Telescopic one-pot condensation-hydroamination strategy for the synthesis of optically pure L-phenylalanines from benzaldehydes

A chemo-enzymatic telescopic approach was designed for the synthesis of L-arylalanines in high yield and optical purity, starting from commercially available and inexpensive substituted benzaldehydes. The method exploits a chemical Knoevenagel–Doebner condensation (optimised to give complete conversions in a short reaction time, employing microwave irradiation) and a biocatalytic phenylalanine ammonia lyase mediated hydroamination (for the stereoselective addition of ammonia). The two reactions can be run sequentially in one pot, bringing together the advantages of chemical and biological catalysis. The preparative applicability was demonstrated with the synthesis of five L-dihalophenylalanines (71–84% yield, 98–99% ee) of relevance as molecular probes, for medicinal chemistry and for the synthesis of pharmaceutical ingredients.

Novel chiral open-chain pyridoxamine catalyst and synthesis method and application thereof

The invention relates to a novel chiral open-chain pyridoxamine catalyst and a synthesis method and application thereof. The structural general formula of the pyridoxamine catalyst is shown in the specification, wherein R1, R2, R3 and R4 are one of hydrogen, C1-24 alkyl, C1-24 alkyl containing substituent groups, substances shown in the specification and halogen, the substituent groups on C1-24 alkyl are a substance shown in the specification or a substance shown in the specification or a substance shown in the specification or O-Rw or S-Rw' or halogen, and Rx, Rx', Ry, Ry', Ry'', Rz, Rz', Rw and Rw' are one of hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, tertiary butyl, cyclopentyl, cyclohexyl, cycloheptyl, phenyl, benzyl, (1-phenyl)ethyl, 1-naphthyl, 2-naphthyl and halogen. Compared with the prior art, the pyridoxamine catalyst can achieve rapid and efficient synthesis of chiral amino acid, the preparation raw materials are easy to obtain, reaction conditions are mild, cost is low, and when the novel chiral open-chain pyridoxamine catalyst is used for a transamination reaction, the conditions are mild, and the reaction is stable.

A new type of chiral-pyridoxamines for catalytic asymmetric transamination of α-keto acids

A new type of chiral pyridoxamines bearing an adjacent chiral stereocenter has been developed via multi-step synthesis. The pyridoxamines displayed catalytic activity in asymmetric transamination of α-keto acids to give a variety of optically active amino acids in 27–78% yields with 34–62% ee's under very mild conditions. This work provides a synthetic strategy to construct new chiral pyridoxamines using bromopyridine 7 as a key synthon and also represents an early example of the applications of chiral pyridoxamines in asymmetric catalysis.

The bacterial ammonia lyase EncP: A tunable biocatalyst for the synthesis of unnatural amino acids

Enzymes of the class I lyase-like family catalyze the asymmetric addition of ammonia to arylacrylates, yielding high value amino acids as products. Recent examples include the use of phenylalanine ammonia lyases (PALs), either alone or as a gateway to deracemization cascades (giving (S)- or (R)-α-phenylalanine derivatives, respectively), and also eukaryotic phenylalanine aminomutases (PAMs) for the synthesis of the (R)-β-products. Herein, we present the investigation of another family member, EncP from Streptomyces maritimus, thereby expanding the biocatalytic toolbox and enabling the production of the missing (S)-β-isomer. EncP was found to convert a range of arylacrylates to a mixture of (S)-α- and (S)-β-arylalanines, with regioselectivity correlating to the strength of electron-withdrawing/-donating groups on the ring of each substrate. The low regioselectivity of the wild-type enzyme was addressed via structure-based rational design to generate three variants with altered preference for either α- or β-products. By examining various biocatalyst/substrate combinations, it was demonstrated that the amination pattern of the reaction could be tuned to achieve selectivities between 99:1 and 1:99 for β:α-product ratios as desired.

Asymmetric synthesis of chiral heterocyclic amino acids via the alkylation of the Ni(II) complex of glycine and alkyl halides

An investigation into the reactivity profile of alkyl halides has led to the development of a new method for the asymmetric synthesis of chiral heterocyclic amino acids. This protocol involves the asymmetric alkylation of the Ni(II) complex of glycine to form an intermediate, which then decomposes to form a series of valuable chiral amino acids in high yields and with excellent diastereoselectivity. The chiral amino acids underwent a smooth intramolecular cyclization process to afford the valuable chiral heterocyclic amino acids in high yields and enantioselectivities. This result paves the way for the development of a new synthetic method for chiral heterocyclic amino acids.

Phenylalanine aminomutase-catalyzed addition of ammonia to substituted cinnamic acids: A route to enantiopure α- and β-amino acids

(Chemical Equation Presented) An approach is described for the synthesis of aromatic α- and β-amino acids that uses phenylalanine aminomutase to catalyze a highly enantioselective addition of ammonia to substituted cinnamic acids. The reaction has a broad scope and yields substituted α- and β-phenylalanines with excellent enantiomeric excess. The regioselectivity of the conversion is determined by substituents present at the aromatic ring. A box model for the enzyme active site is proposed, derived from the influence of the hydrophobicity of substituents on the enzyme affinity toward various substrates.

Use of whole cell culture of Aeromonas sp. as enantioselective scavenger: A facile preparation of l-amino acid derivatives in high enantiomeric excess

The bacterium Aeromonas sp. (CGMCC 2226) can enantioselectively scavenge d-isomer, making l-amino acid derivatives (AADs) in high ee. The enantioselective scavenger (ES) has shown a broad substrate scope. Eleven l-AADs, Phe derivatives substituted with methyl-, mono- and dichloro-, bromo-, and nitro-group, were produced in high ee from corresponding racemates.

Chemistry of unprotected amino acids in aqueous solution: Direct bromination of aromatic amino acids with bromoisocyanuric acid sodium salt under strong acidic condition

Brominations of unprotected aromatic amino acids such as phenylalanine, tyrosine, and glycine, with bromoisocyanuric acid mono sodium salt (BICA-Na) were conducted in 60% aq. H2SO4 at 0°C to give a mixture of mono-brominated products in good yield. Unexpectedly, meta-bromophenylglycine was obtained as main product accompanied by ortho- and para-substituted products, while phenylalanine gave only ortho- and para-substituted products. Bromination of 2-phenylethylamine or benzylamine showed a tendency similar to the corresponding amino acids.