3-Trifluoromethyl-L-Phenylalanine is a fluorinated, proteinogenic amino acid analogue in which the phenylalanine side chain is substituted at the 3-position with a trifluoromethyl group, retaining the α-amino and α-carboxyl functionality of an amino acid while featuring a chiral center consistent with the L-configuration indicated in the name. The molecule bears a primary amino group and a carboxylic acid (or its corresponding zwitterionic form under aqueous conditions) alongside a hydrophobic aromatic ring whose electron-withdrawing CF3 substituent modulates side-chain polarity and aromatic character for structure-property studies. It is used as a substrate analogue in peptide synthesis and protein engineering workflows to introduce the CF3-bearing phenylalanine residue for conformational, binding, and structure-activity investigations, as well as in analytical method development where fluorinated amino acids provide distinct spectroscopic and chromatographic behavior.
CAT No: CP16701
CAS No:14464-68-7
Synonyms/Alias:14464-68-7;3-(Trifluoromethyl)-L-phenylalanine;(S)-2-Amino-3-(3-(trifluoromethyl)phenyl)propanoicacid;L-3-Trifluoromethylphenylalanine;(2S)-2-amino-3-[3-(trifluoromethyl)phenyl]propanoicacid;3-Trifluoromethyl-L-Phenylalanine;L-3-TRIFLUOROMETHYLPHE;L-3-Trifluoromethyphenylalanine;(S)-2-Amino-3-[3-(trifluoromethyl)phenyl]propionicacid;TRIFLUOROMETHYPHE;82317-79-1;D-3-Trifluoromethyphenylalanine;AC1MCRU4;SCHEMBL44156;77092_ALDRICH;H-PHE(3-CF3)-OH;L-PHE(3-CF3)-OH;3-(Trifluoromethyl)phenylalanine;77092_FLUKA;CTK3J1764;MolPort-001-777-569;ZINC2170205;7133AA;CT-388;MFCD00044945
3-Trifluoromethyl-L-Phenylalanine is an L-phenylalanine analog bearing a trifluoromethyl substituent at the meta position of the aromatic ring, making it a non-natural aromatic amino acid building block for structure-activity and conformational studies. Its strongly electron-withdrawing CF3 group is frequently leveraged in medicinal chemistry to modulate physicochemical properties and aromatic interactions while maintaining an amino acid backbone suitable for peptide and peptidomimetic assembly. Researchers also use this residue as a defined, stereochemically consistent aromatic variant when preparing standards, SAR libraries, or modified peptide fragments.
1. Peptidomimetic Building Blocks
3-Trifluoromethyl-L-Phenylalanine is used by medicinal chemistry teams to incorporate a CF3-substituted aromatic residue into peptidomimetics and constrained peptide analogs for SAR studies. The meta-CF3 substitution provides a distinct electronic and steric profile compared with unsubstituted phenylalanine, enabling systematic evaluation of how aromatic ring electronics influence potency-related trends in lead optimization programs. In practice, this amino acid is selected when downstream workflows require a single, well-defined stereochemical building block that can be assembled into short peptide fragments or larger analogs for biological screening campaigns and structure-property correlation.
2. Peptide Synthesis Residue
3-Trifluoromethyl-L-Phenylalanine serves as a specialized amino acid building block for custom peptide synthesis where a meta-trifluoromethyl phenylalanine side chain is needed as a stable, non-natural residue. Peptide synthesis groups commonly choose this compound for preparing modified peptides used in chemical biology, receptor/ligand interaction mapping, and mechanistic studies where the aromatic CF3 group acts as a tunable substituent. Because the product is an L-configured amino acid analog, it supports consistent stereochemical placement in the peptide backbone, which is important for comparing analog series and interpreting structure-activity relationships across a library of modified sequences.
3. Medicinal Chemistry SAR Libraries
3-Trifluoromethyl-L-Phenylalanine is widely used in small-molecule and peptide-derived medicinal chemistry programs to generate analog series that probe the impact of fluorinated aromatic motifs. The CF3 group can strongly influence lipophilicity, metabolic stability trends, and hydrogen-bonding patterns around the aromatic ring, making this residue a practical choice for systematic SAR exploration when aromatic electronics are a key variable. Development chemists typically employ this amino acid as a defined intermediate to construct CF3-bearing fragments that feed into larger synthesis routes, supporting parallel synthesis of analogs for profiling and lead refinement.
4. Analytical Reference Standards
3-Trifluoromethyl-L-Phenylalanine is also used as a defined reference material for analytical method development and quantitation workflows involving CF3-substituted aromatic amino acid motifs. Analytical chemistry teams prepare calibration or characterization standards when monitoring modified peptides, peptide fragments, or amino acid-derived intermediates by LC-MS or related techniques, where an authentic compound improves identification confidence and supports consistent response behavior across runs. The stereodefined L-configuration and the unique CF3 mass signature make it particularly useful for distinguishing this residue from closely related aromatic amino acid analogs during method validation and routine analytical checks.
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