873429-58-4

Usage

Uses

Used in Research Applications:
2,3,4-Trifluoro-L-phenylalanine is utilized as a probe for studying protein folding and stability. Its unique structure allows researchers to investigate the effects of fluorine substitution on the behavior of proteins, providing insights into the fundamental processes of protein conformation and function.
Used in Pharmaceutical Development:
In the pharmaceutical industry, 2,3,4-Trifluoro-L-phenylalanine serves as a building block for the synthesis of fluorinated compounds. The incorporation of fluorine atoms can significantly influence the pharmacokinetic and pharmacodynamic properties of drug molecules, potentially leading to improved therapeutic agents with enhanced efficacy and selectivity.
Used in Material Science:
2,3,4-Trifluoro-L-phenylalanine is also valuable in the development of new materials. Its unique properties can be harnessed to create novel compounds with specific characteristics, such as increased stability or altered reactivity, which can be applied in various industrial processes or technologies.

InChI:InChI=1/C9H8F3NO2/c10-5-2-1-4(7(11)8(5)12)3-6(13)9(14)15/h1-2,6H,3,13H2,(H,14,15)/t6-/m0/s1

Upstream product

• 324027-89-6 diethyl 2-acetamido-2-(2,3,4-trifluorobenzyl)malonate 
• 324027-95-4 2-acetylamino-2-(2,3,4-trifluoro-benzyl)-malonic acid 
• 157911-55-2 1-(bromomethyl)-2,3,4-trifluorobenzene 
• 324028-07-1 acetyl-D-2,3,4-trifluorophenylalanine 
• 324028-01-5 acetyl-DL-2,3,4-trifluorophenylalanine 

Relevant academic research and scientific papers

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.