481660-72-4

Basic information

• Product Name: 2,4,6-Trifluoro-L-Phenylalanine
• Synonyms: 2,4,6-Trifluoro-L-Phenylalanine;L-2,4,6-Trifluoro-Phe-OH;(S)-2-AMINO-3-(2,4,6-TRIFLUOROPHENYL)PROPANOIC ACID;(2S)-2-amino-3-(2,4,6-trifluorophenyl)propanoic acid
• CAS NO: 481660-72-4
• Molecular Formula: C9H8F3NO2
• Molecular Weight: 219.1605296
• Mol File: 481660-72-4.mol

Chemical Properties

• Appearance: /
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 2,4,6-Trifluoro-L-Phenylalanine(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4,6-Trifluoro-L-Phenylalanine(481660-72-4)
• EPA Substance Registry System: 2,4,6-Trifluoro-L-Phenylalanine(481660-72-4)

Safety Data

• Hazardous Substances Data: 481660-72-4(Hazardous Substances Data)

Usage

Uses

Used in Medicinal Chemistry and Drug Development:
2,4,6-Trifluoro-L-Phenylalanine is used as a building block for the synthesis of new pharmaceutical compounds, leveraging its enhanced interaction with biological targets to improve the efficacy and selectivity of drug candidates.
Used in Biochemical Probes:
2,4,6-Trifluoro-L-Phenylalanine is used as a biochemical probe to study the function of specific proteins and enzymes in biological systems, providing insights into their mechanisms of action and potential therapeutic applications.
Used in Disease and Disorder Treatment:
2,4,6-Trifluoro-L-Phenylalanine has been studied for its potential use in the treatment of various diseases and disorders, owing to its unique structure and ability to modulate biological processes.
Used in Research and Development:
2,4,6-Trifluoro-L-Phenylalanine is utilized in research and development to explore its potential applications in different therapeutic areas, including but not limited to, oncology, neurology, and metabolic disorders, by understanding its interactions with specific biological targets and pathways.

Upstream product

• 324027-93-2 diethyl 2-acetamido-2-(2,4,6-trifluorobenzyl)malonate 
• 151411-98-2 2-(bromomethyl)-1,3,5-trifluorobenzene 
• 324028-11-7 acetyl-D-2,4,6-trifluorophenylalanine 
• 324028-05-9 acetyl-DL-2,4,6-trifluorophenylalanine 
• 324027-99-8 2-acetylamino-2-(2,4,6-trifluoro-benzyl)-malonic acid 

Relevant articles and documents

Exploration of the role of phenylalanine in the thrombin receptor tethered-ligand peptide by substitution with a series of trifluorophenylalanines

The thrombin receptor-tethered ligand SFLLRNP (abbreviation formed by one letter amino acid codes expressing Ser-Phe-Leu-Leu-Arg-Asn-Pro) consists of the Phe-2 residue essential for the receptor activation. In order to explore the molecular characteristics of this Phe-2-phenyl, a series of trifluorophenylalanines [(F3)Phe] was incorporated into this S/Phe/LLRNP for evaluation of their ability to induce the human platelet aggregation. A complete set of (F3)Phe in the L-configuration, namely, (2,3,4-F3)Phe, (2,3,5-F3)Phe, (2,3,6-F3)Phe, (2,4,5-F3)Phe, (2,4,6-F3)Phe, and (3,4,5-F3)Phe, was prepared from trifluorobenzyl bromides and diethyl acetamidomalonate. S/(2,3,4-F3)Phe/LLRNP was equipotent to S/Phe/LLRNP, while (2,4,5-F3)Phe-containing analog was almost twice as potent as those. (2,4,6-F3)Phe-analog exhibited about a half of the activity of S/Phe/LLRNP. (3,4,5-F3)Phe-, (2,3,5-F3)Phe-, and (2,3,6-F3)Phe-analogs were very weak. The analysis of these assay results suggested that Phe-2-phenyl of SFLLRNP is in the edge-to-face CH/π interaction with the receptor aromatic group, utilizing the Phe-2-phenyl edge along with benzene hydrogens at position 2-3 or 5-6. The computer-assisted semi-empirical molecular orbital calculations by MOPAC showed that the fluorine atom decreases the electron density of its ortho, meta, and para hydrogens, and thus increases their acidity more strongly in that order. All these suggested that H → F replacements reinforce the edge-to-face CH/π interaction to enhance biological activity. The H → F replacement on the Phe-phenyl group was found to render an effective structural examination; i.e., to identify the hydrogens in the CH/π interaction, and to intensify the CH/π interaction.