4-Trifluoromethyl-L-Phenylalanine is an L-phenylalanine derivative bearing a trifluoromethyl substituent at the para (4-) position of the benzyl side chain, classifying it as a fluorinated, non-natural aromatic amino acid. The molecule contains a free amino group and a free carboxyl group, and its side chain features a strongly electron-withdrawing CF3 functionality that can influence hydrophobicity, aromatic interactions, and conformational preferences in peptide contexts. As a chemically defined building block for peptide synthesis and structure-activity or binding studies, it is used to introduce the CF3-bearing aromatic residue into synthetic peptides and to support analytical method development and molecular labeling experiments where fluorinated handles aid detection or characterization.
CAT No: CP16801
CAS No:114926-38-4
Synonyms/Alias:4-(Trifluoromethyl)-L-phenylalanine;114926-38-4;(2S)-2-amino-3-[4-(trifluoromethyl)phenyl]propanoic acid;L-Phenylalanine, 4-(trifluoromethyl)-;122839-56-9;(S)-2-amino-3-(4-(trifluoromethyl)phenyl)propanoic acid;MFCD00044946;DTXSID801347041;4-Trifluoromethyl-L-Phenylalanine;L-4-TRIFLUOROMETHYLPHE;3832-75-5;p-trifluoromethylphenylalanine;SCHEMBL43862;(S)-2-Amino-3-[4-(trifluoromethyl)phenyl]propionic acid;CHEBI:232918;DTXCID301775756;AKOS010397236;AKOS015854053;AB02000;AC-5864;CS-W014678;FT43466;HY-W013962;AC-12382;DS-10718;PD196932;EN300-199895;H11871;4-(Trifluoromethyl)-L-phenylalanine, >=99.0%;4-Trifluoromethyl-L-phenylalanine (H-L-Phe(4-CF3)-OH);822-926-1;
4-Trifluoromethyl-L-Phenylalanine is a fluorinated, non-natural phenylalanine analog bearing a para-trifluoromethyl substituent on the aromatic side chain. As an L-configured amino acid building block, it is frequently used in peptide and peptidomimetic chemistry to introduce strong hydrophobic character and distinctive electronic effects associated with the CF3 group. This reagent is also used in medicinal chemistry programs where aromatic fluorination patterns are leveraged to tune physicochemical properties during lead optimization.
1. Peptidomimetic Building Block
4-Trifluoromethyl-L-Phenylalanine is used by peptide chemistry groups to incorporate an aryl CF3 side chain into short peptides, constrained analogs, and peptidomimetics. The para-CF3 functionality provides a compact, metabolically stable aromatic modification that is commonly selected when researchers want to probe structure-property relationships driven by lipophilicity and electronic effects. In downstream workflows, this amino acid supports the synthesis of analog libraries for SAR studies, including analogs designed to compare aromatic substitution patterns while keeping the backbone stereochemistry consistent.
2. Medicinal Chemistry SAR Studies
4-Trifluoromethyl-L-Phenylalanine is a practical building block for medicinal chemistry teams developing small-molecule or peptide-like inhibitors where aromatic substitution is a key design variable. The CF3 group is frequently chosen to modulate overall hydrophobicity and aromatic electronics, enabling systematic evaluation of how para-trifluoromethyl substitution impacts potency-related structure features in analog series. Researchers typically use this reagent to prepare defined intermediates and standardized analogs for parallel testing, ensuring that the CF3-bearing stereochemical element is introduced reproducibly rather than via variable substitution routes.
3. Pharmaceutical Intermediate Development
4-Trifluoromethyl-L-Phenylalanine is also used as a defined chiral intermediate in the synthesis of CF3-substituted fragments and amino-acid-derived intermediates for further derivatization. Process development and custom synthesis teams often rely on amino acid building blocks to maintain stereochemical integrity while assembling larger targets, including protected derivatives that feed into subsequent coupling or functional group transformations. This makes the compound valuable for route scouting and scale-up efforts where a single, well-characterized stereochemical unit is carried through multiple downstream steps.
4. Analytical Reference Material
4-Trifluoromethyl-L-Phenylalanine is used in analytical method development and reference standard preparation for workflows that quantify or confirm CF3-containing amino acid motifs. In LC-MS and related characterization pipelines, having a chemically defined, stereochemically specified amino acid helps researchers validate retention behavior, fragmentation patterns, and identity confirmation for analogs that include the para-trifluoromethyl aromatic side chain. This is particularly useful when monitoring synthetic intermediates or verifying the composition of peptide/peptidomimetic libraries where CF3 substitution is a distinguishing structural feature.
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