24250-84-8

Basic information

• Product Name: 4-Bromo-L-phenylalanine
• Synonyms: (S)-3-(4-Bromophenyl)-2-aminopropanoic acid;(S)-3-(4-Bromophenyl)-2-aminopropionic acid;L-4-Bromo-phe-OH;4-Bromo-L-phenylalan;(S)-4-Bromophenylalanine Hydrochloride Salt;L-4-Br-Phe-OH 4-BroMo-L-Phenylalanine;4-Bromo-L-phenylalanine≥ 99% (HPLC);L-Phe(4-Br)-OH
• CAS NO: 24250-84-8
• Molecular Formula: C₉H₁₀BrNO₂
• Molecular Weight: 244.09
• EINECS: 237-941-3
• Product Categories: Peptide Synthesis;Phenylalanine Derivatives;Unnatural Amino Acid Derivatives;a-amino;Amino Acids;Phenylalanine analogs and other aromatic alpha amino acids;Chiral Reagent;Phenylalanine [Phe, F];Unusual Amino Acids
• Mol File: 24250-84-8.mol
• Article Data: 24

Chemical Properties

• Melting Point: ~265 °C (dec.)
• Boiling Point: 368.4 °C at 760 mmHg
• Flash Point: 176.6 °C
• Appearance: /
• Density: 1.588 g/cm³
• Vapor Pressure: 6.06E-07mmHg at 25°C
• Storage Temp.: Store at RT.
• Solubility: Methanol (Slightly, Sonicated), Water (Slightly, Heated, Sonicated)
• PKA: 2.18±0.10(Predicted)
• Stability: Hygroscopic
• BRN: 2212159
• CAS DataBase Reference: 4-Bromo-L-phenylalanine(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Bromo-L-phenylalanine(24250-84-8)
• EPA Substance Registry System: 4-Bromo-L-phenylalanine(24250-84-8)

Safety Data

• Hazard Codes: T,Xi
• Statements: 25
• Safety Statements: 45
• RIDADR: UN2811
• WGK Germany: 3
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 24250-84-8(Hazardous Substances Data)

Usage

Chemical Properties

Off-white powder

InChI:InChI=1/C9H10BrNO2.ClH/c10-7-3-1-6(2-4-7)5-8(11)9(12)13;/h1-4,8H,5,11H2,(H,12,13);1H/t8-;/m0./s1

Upstream product

• 39801-57-5 N-trifluoroacetyl-p-bromo-DL-phenylalanine 
• 123052-82-4 tert-butyl (2S,5S)-5-(4-bromobenzyl)-2-(tert-butyl)-3-methyl-4-oxo-1-imidazolidinecarboxylate 
• 63-91-2 L-phenylalanine 
• 14091-15-7 p-bromo-DL-phenylalanine 
• 589-15-1 1-bromomethyl-4-bromobenzene 
• 1200-07-3 trans-4-bromocinnamic acid 
• 171095-12-8 N-acetyl-4-bromophenylalanine 
• 444726-88-9 H-Phe(4-Br)-OMe hydrochloride 
• 1200-07-3 3-(4-bromophenyl)acrylic acid 
• 39773-47-2 3-amino-3-(4'-bromophenyl)propanoic acid 
• 198561-04-5 Fmoc-4-bromo-L-phenylalanine 
• 213318-44-6 N-Boc-indole-2-boronic acid 
• 191162-39-7 quinolin-3-ylboronic acid 
• 1122-91-4 4-bromo-benzaldehyde 

Downstream Products

• 99359-32-7 (S)-2-amino-3-(4-bromophenyl)propionic acid methyl ester hydrochloride 
• 1100357-99-0 (S)-2-(benzyloxycarbonylamino)-3-(4-bromophenyl)propanoic acid 
• 99359-33-8 (S)-methyl 2-amino-3-(4-bromophenyl)propanoate 
• 1141478-88-7 (S)-3-(4-bromophenyl)-2-hydroxypropionic acid 
• 1141478-88-7 (2R)-3-(4-bromophenyl)-2-hydroxypropanoic acid 
• 500767-10-2 (2S)-2-amino-3-(4-bromophenyl)propanamide 
• 500767-17-9 (2S,5S,6S)-3-aza-2-(p-bromobenzyl)-6-[(tert-butyloxycarbonyl)amino]-5-hydroxy-7-phenylheptanoyl amide 
• 500767-38-4 Pyridine-2-carboxylic acid ((S)-1-{(1S,2S)-1-benzyl-3-[(S)-2-(4-bromo-phenyl)-1-carbamoyl-ethylamino]-2-hydroxy-propylcarbamoyl}-2-methyl-propyl)-amide 
• 500767-24-8 (2S,5S,6S)-3-aza-3-(benzyloxycarbonyl)-2-(p-bromobenzyl)-6-[(tert-butyloxycarbonyl)amino]-5-hydroxy-7-phenylheptanoyl amide 
• 500767-08-8 Pyridine-2-carboxylic acid ((S)-1-{(1S,2S)-1-benzyl-3-[(S)-5-(4-bromo-benzyl)-2,4-dioxo-imidazolidin-1-yl]-2-hydroxy-propylcarbamoyl}-2-methyl-propyl)-amide 
• 558467-56-4 (2S,5S,6S)-3-aza-3-(benzyloxycarbonyl)-2-(p-bromobenzyl)-6-[[(tert-butyloxycarbonyl)-L-valinyl]amino]-5-hydroxy-7-phenylheptanoyl amide 
• 232277-15-5 N-(2,6-dichlorobenzoyl)-4-bromo-L-phenylalanine methyl ester 
• 232271-19-1 [14C]-TR-14035 

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.

Colony-wise Analysis of a Theonella swinhoei Marine Sponge with a Yellow Interior Permitted the Isolation of Theonellamide i

There are several examples of marine organisms whose metabolic profiles differ among conspecifics inhabiting the same region. We have analyzed the metabolic profile of each colony of a Theonella swinhoei marine sponge with a yellow interior and noticed the patchy distribution of one metabolite. This compound was isolated and its structure was studied by a combination of spectrometric analyses and chemical degradation, showing it to be a congener in the theonellamide class of bicyclic peptides. Theonellamides had previously been isolated by us only from T. swinhoei with a white interior and not from those with a yellow interior.

Kinetic Resolution of Aromatic β-Amino Acids Using a Combination of Phenylalanine Ammonia Lyase and Aminomutase Biocatalysts

An enzymatic strategy for the preparation of (R)-β-arylalanines employing phenylalanine aminomutase and ammonia lyase (PAM and PAL) enzymes has been demonstrated. Candidate PAMs with the desired (S)-selectivity from Streptomyces maritimus (EncP) and Bacillus sp. (PabH) were identified via sequence analysis using a well-studied template sequence. The newly discovered PabH could be linked to the first ever proposed biosynthesis of pyloricidin-like secondary metabolites and was shown to display better β-lyase activity in many cases. In spite of this, a method combining the higher conversion of EncP with a strict α-lyase from Anabaena variabilis (AvPAL) was found to be more amenable, allowing kinetic resolution of five racemic substrates and a preparative-scale reaction with >98% (R) enantiomeric excess. This work represents an improved and enantiocomplementary method to existing biocatalytic strategies, allowing simple product separation and modular telescopic combination with a preceding chemical step using an achiral aldehyde as starting material. (Figure presented.).