99295-78-0

Basic information

• Product Name: 3-Bromo-D-phenylalanine
• Synonyms: 3-Bromo-D-phenylalanine
• CAS NO: 99295-78-0
• Molecular Formula: C9H10BrNO2
• Molecular Weight: 244.09
• Product Categories: Amino Acids
• Mol File: 99295-78-0.mol
• Article Data: 15

Chemical Properties

• Boiling Point: 368.4 °C at 760 mmHg
• Flash Point: 176.6 °C
• Appearance: /
• Density: 1.588 g/cm³
• Storage Temp.: Store at RT.
• PKA: 2.16±0.10(Predicted)
• CAS DataBase Reference: 3-Bromo-D-phenylalanine(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Bromo-D-phenylalanine(99295-78-0)
• EPA Substance Registry System: 3-Bromo-D-phenylalanine(99295-78-0)

Safety Data

• Hazardous Substances Data: 99295-78-0(Hazardous Substances Data)

Usage

Description

3-Bromo-D-phenylalanine is a non-natural, chiral amino acid derivative that features a bromine atom at the 3-position of the phenyl ring. It is an important building block in organic synthesis and has potential applications in various fields due to its unique structural properties.

Uses

Used in Pharmaceutical Industry:
3-Bromo-D-phenylalanine is used as a key intermediate in the synthesis of various pharmaceutical compounds. One notable example is its role in the production of 3-(Methylsulfonyl)-D-phenylalanine Hydrochloride (M326188), which has been identified as a potent LFA-1/ICAM-1 Antagonist SAR 1118.
Used in Ophthalmic Solutions:
In the ophthalmic industry, 3-Bromo-D-phenylalanine is utilized in the development of an Ophthalmic Solution for treating dry eye. The synthesized compound, 3-(Methylsulfonyl)-D-phenylalanine Hydrochloride, serves as an effective treatment for this condition, demonstrating the versatility of 3-Bromo-D-phenylalanine in addressing specific medical needs.

Upstream product

• 15017-44-4 diethyl (acetylamino)<(3-bromophenyl)methyl>propanedioate 
• 823-78-9 meta-bromobenzyl bromide 
• 82278-73-7 (2S)-3-(3-bromophenyl)-2-[(tert-butoxycarbonyl)amino]propanoic acid 
• 14473-91-7 3-Bromocinnamic acid 
• 14473-91-7 3-bromocinnamic acid 
• 3132-99-8 m-bromobenzoic aldehyde 
• 117391-50-1 3-amino-3-(3-bromo-phenyl)-propionic acid 
• 30163-20-3 2-amino-3-(3-bromophenyl)propanoic acid 

Downstream Products

• 875782-96-0 C₁₀H₁₂BrNO₂ 
• 164172-95-6 (S)-3-([1,1'-biphenyl]-3-yl)-2-aminopropanoic acid 

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.

Organocatalytic Enantioselective Addition of α-Aminoalkyl Radicals to Isoquinolines

With a dual organocatalytic system involving a chiral phosphoric acid and a dicyanopyrazine-derived chromophore (DPZ) photosensitizer and under the irradiation with visible light, an enantioselective Minisci-type addition of α-amino acid-derived redox-active esters (RAEs) to isoquinolines has been developed. A variety of prochiral α-aminoalkyl radicals generated from RAEs were successfully introduced on isoquinolines, providing a range of valuable α-isoquinoline-substituted chiral secondary amines in high yields with good to excellent enantioselectivities.

Design, synthesis, and functional assessment of Cmpd-15 derivatives as negative allosteric modulators for the β2-adrenergic receptor

The β2-adrenergic receptor (β2AR), a G protein-coupled receptor, is an important therapeutic target. We recently described Cmpd-15, the first small molecule negative allosteric modulator (NAM) for the β2AR. Herein we report in details the design, synthesis and structure-activity relationships (SAR) of seven Cmpd-15 derivatives. Furthermore, we provide in a dose-response paradigm, the details of the effects of these derivatives in modulating agonist-induced β2AR activities (G-protein-mediated cAMP production and β-arrestin recruitment to the receptor) as well as the binding affinity of an orthosteric agonist in radio-ligand competition binding assay. Our results show that some modifications, including removal of the formamide group in the para-formamido phenylalanine region and bromine in the meta-bromobenzyl methylbenzamide region caused dramatic reduction in the functional activity of Cmpd-15. These SAR results provide valuable insights into the mechanism of action of the NAM Cmpd-15 as well as the basis for future development of more potent and selective modulators for the β2AR based on the chemical scaffold of Cmpd-15.