267225-27-4

Basic information

• Product Name: D-2-Bromophenylalanine
• Synonyms: H-D-PHE(2-BR)-OH;H-O-BROMO-D-PHE-OH;D-2-BROMOPHE;D-2-BROMOPHENYLALANINE;2-BROMO-D-PHENYLALANINE;(R)-2-AMINO-3-(2-BROMO-PHENYL)-PROPIONIC ACID;RARECHEM BK PT 0040;(2R)-2-amino-3-(2-bromophenyl)propanoic acid
• CAS NO: 267225-27-4
• 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: 267225-27-4.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 363.2 °C at 760 mmHg
• Flash Point: 173.4 °C
• Appearance: White to off-white/Powder
• Density: 1.588g/cm³
• Vapor Pressure: 6.53E-06mmHg at 25°C
• Refractive Index: 1.608
• Storage Temp.: Store at -15°C
• PKA: 2.16±0.10(Predicted)
• CAS DataBase Reference: D-2-Bromophenylalanine(CAS DataBase Reference)
• NIST Chemistry Reference: D-2-Bromophenylalanine(267225-27-4)
• EPA Substance Registry System: D-2-Bromophenylalanine(267225-27-4)

Safety Data

• Hazard Codes: Xi
• Hazardous Substances Data: 267225-27-4(Hazardous Substances Data)

Usage

Chemical Properties

White to off-white powder

InChI:InChI=1/C9H10BrNO2/c10-7-4-2-1-3-6(7)5-8(11)9(12)13/h1-4,8H,5,11H2,(H,12,13)/t8-/m1/s1

Upstream product

• 1991-79-3 2-amino-3-(2-bromophenyl)propanoic acid 
• 7345-79-1 2-bromocinnamic acid 
• 120240-65-5 3-(2-bromophenyl)-2-oxopropanoic acid 
• 3060-50-2 2,2-diphenylglycine 

Downstream Products

• 773033-36-6 methyl 6-bromo-1,2,3,4-tetrahydroisoquinoline-3-carboxylate 
• 721880-65-5 methyl 2-amino-3-(3-bromophenyl)propanoate 
• 938462-34-1 (2R)-2-amino-3-(2-bromophenyl)propan-1-ol 

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.

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.

Enantioselective scavenging using homogenate of Rhodotorula graminis: a facile preparation of d-amino acid derivatives in enantiopure form

An enantioselective scavenger (ES) comprised homogenate of Rhodotorula graminis containing multiple enzymes can enantioselectively remove l-enantiomer in a racemic mixture of amino acid derivatives (AADs), yielding d-enantiomer in high ee. Thirteen non-proteinogenic AADs were produced in enantiopure d form. The method appears to be an efficient cleaning and preparative strategy which can be applied to the production of d-AADs in high ee by enantioselectively scavenging the 'l-contaminants'.