2-Trifluoromethyl-D-Phenylalanine is a non-natural, stereochemically defined amino acid derivative featuring a D-configuration at the α-carbon and a benzyl side chain bearing a trifluoromethyl substituent at the 2-position relative to the benzylic attachment. The molecule contains a free amino group and a free carboxyl group, with the electron-withdrawing CF3 moiety on the aromatic ring providing distinctive hydrophobic and fluorinated physicochemical character that can influence peptide-coupling behavior and conformational preferences. It is used in peptide and structure-activity studies, chemical biology labeling strategies, and analytical method development where fluorinated, phenylalanine-like building blocks are required to probe binding interactions, stability, or structure-property relationships.
CAT No: CP16602
CAS No:130930-49-3
Synonyms/Alias:2-(Trifluoromethyl)-D-phenylalanine;130930-49-3;D-2-Trifluoromethylphenylalanine;(R)-2-AMINO-3-(2-(TRIFLUOROMETHYL)PHENYL)PROPANOICACID;(2R)-2-amino-3-[2-(trifluoromethyl)phenyl]propanoicacid;D-2-TRIFLUOROMETHYLPHE;(R)-2-Amino-3-[2-(trifluoromethyl)phenyl]propionicacid;2-Trifluoromethyl-D-Phenylalanine;AC1OCXQC;87028_ALDRICH;D-PHE(2-CF3)-OH;SCHEMBL503201;H-D-PHE(2-CF3)-OH;87028_FLUKA;CTK0H3931;MolPort-001-777-568;D-2-TRIFLUOROMETHYL-PHE-OH;ACN-S002962;ZINC2169782;5619AA;ANW-61446;PC8366;AKOS016843045;AB10092;AC-5861
2-Trifluoromethyl-D-Phenylalanine is a D-configured, non-proteinogenic phenylalanine analog bearing a trifluoromethyl substituent on the aromatic ring, providing distinct steric and electronic properties compared with native phenylalanine. This fluorinated amino acid building block is frequently used in peptidomimetic and medicinal chemistry programs where fluorine-driven effects are leveraged to modulate conformation, physicochemical behavior, and structure-activity relationships. Its stereochemical definition makes it a practical choice for designing stereochemically controlled peptide analogs and non-natural residue replacements in synthetic sequences.
1. Peptidomimetic Building Blocks
2-Trifluoromethyl-D-Phenylalanine is used as a stereodefined amino acid building block for constructing peptidomimetic scaffolds and non-natural peptide analogs in custom peptide synthesis. Medicinal chemistry groups incorporate this residue to probe how an aryl-trifluoromethyl motif influences local side-chain packing and overall molecular properties in lead optimization series. The D-configuration supports the preparation of stereochemically defined analogs for SAR studies, including D-amino acid-containing sequences designed to systematically vary backbone stereochemistry while maintaining a phenylalanine-like side chain framework.
2. Structure-Activity Relationship Studies
2-Trifluoromethyl-D-Phenylalanine supports SAR and analog design workflows in small-molecule and peptide-based drug discovery, where fluorinated aromatic substituents are used to tune lipophilicity, metabolic stability proxies, and binding-site complementarity through electronic and steric effects. Researchers commonly employ this building block to generate focused libraries that compare substitution patterns on the phenyl ring while holding the amino acid stereochemistry constant. In these programs, the defined D-stereochemistry and the trifluoromethyl-bearing aromatic side chain make it a convenient reagent for systematic structure variation without changing the overall residue identity class.
3. Protease-Resistant Analogue Development
2-Trifluoromethyl-D-Phenylalanine is frequently selected for developing D-amino acid-containing peptide and peptidomimetic analogs used in chemical biology and preclinical lead characterization, where researchers aim to improve resistance to enzymatic degradation as part of stability optimization. By introducing a non-natural D-residue with a fluorinated aryl side chain, teams can evaluate how stereochemistry and side-chain electronics jointly affect degradation profiles in enzymatic stability assays. This product's role is typically as a defined, sequence-level substitution that enables reproducible comparison across analog series rather than as a general-purpose amino acid.
4. Pharmaceutical Intermediate Synthesis
2-Trifluoromethyl-D-Phenylalanine is also used as a key chiral amino acid intermediate for downstream synthesis of fluorinated peptidomimetics and specialty building blocks in pharmaceutical intermediate development. Process and R&D chemists rely on its defined stereochemistry and fluorinated aromatic motif to ensure consistent incorporation into later-stage coupling, derivatization, or residue-modification steps. This makes the compound valuable when the trifluoromethyl-phenylalanine motif must be carried through multiple synthetic transformations while preserving stereochemical integrity for scale-up and library manufacturing.
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