2,4,6- Trifluoro -D-Phenylalanine is a non-natural, fluorinated amino acid derivative in which the phenylalanine scaffold bears three fluorine substituents at the 2, 4, and 6 positions of the aromatic ring, and the molecule is specified as the D stereoisomer. The amino acid contains a free amino group and a carboxyl group along with a substituted benzyl side chain that incorporates the electron-withdrawing fluorines, providing a distinct physicochemical profile compared with unmodified phenylalanine. This fluorinated D-phenylalanine analogue is used in peptide chemistry and chemical biology as a substrate or building block for structure-activity studies, incorporation into labeled or modified peptides, and analytical method development where aromatic fluorination supports spectroscopic and chromatographic differentiation.
CAT No: CP17002
CAS No:146277-48-7
Synonyms/Alias:(2R)-2-AMINO-3-(2,4,6-TRIMETHYLPHENYL)PROPANOICACID;146277-48-7;D-2,4,6-TRIMETHYLPHENYLALANINE;SCHEMBL5875624;D-Phenylalanine,2,4,6-trimethyl-;ZINC2046233;8548AH;AKOS017482109;AB33644;2,4,6-TRIMETHYL-D-PHENYLALANINE;(R)-2-(2,4,6-Trimethylbenzyl)glycine;(R)-2-AMINO-3-MESITYLPROPANOICACID;I14-37211;(R)-2-AMINO-3-(2,4,6-TRIMETHYL-PHENYL)-PROPIONICACID
2,4,6- Trifluoro -D-Phenylalanine is a D-configured, non-proteinogenic phenylalanine analog bearing three fluorine atoms on the aromatic ring, providing strong electron-withdrawing character and distinctive physicochemical properties relative to native phenylalanine. This fluorinated, chiral amino acid building block is commonly used in peptide and peptidomimetic research where aromatic substitution patterns are leveraged to tune structure, electronics, and analytical detectability. Its stereochemical definition and aryl fluorination make it a practical reagent for downstream incorporation into synthetic sequences and for building well-defined standards in chemical biology workflows.
1. Peptidomimetic Building Blocks
2,4,6- Trifluoro -D-Phenylalanine is used by peptide chemists and medicinal chemistry groups to introduce a highly fluorinated D-phenylalanine motif into peptides, peptidomimetics, and SAR-focused analog series. The tri-fluoro substitution on the aromatic ring provides a defined electronic environment that can influence conformational preferences and aromatic interactions in synthetic constructs, while the D-configuration supports the preparation of stereochemically controlled analogs for structure-activity relationship studies. Researchers typically select this building block when they want a non-natural aromatic amino acid unit that is structurally unambiguous and can be incorporated into defined sequences during custom peptide synthesis.
2. Medicinal Chemistry SAR Studies
2,4,6- Trifluoro -D-Phenylalanine supports medicinal chemistry programs that probe how aromatic ring electronics and steric/electronic effects translate into measurable changes in compound behavior. The 2,4,6-trifluoro pattern is frequently used to create analogs with consistent, reproducible substitution while maintaining a phenylalanine-like backbone for comparative studies against other aromatic variants. Because the compound is a defined, stereochemically specified amino acid analog, it is also used to build focused libraries of fluorinated peptide fragments and constrained peptidomimetic scaffolds used in chemical biology and lead-optimization pipelines.
3. Analytical Standards And Tracing
2,4,6- Trifluoro -D-Phenylalanine is employed for analytical method development and reference standard preparation in workflows that benefit from fluorinated, mass-distinct amino acid analogs. Tri-fluorinated aromatic systems are often chosen because they generate clear mass signatures and are less likely to be confused with endogenous phenylalanine in LC-MS-based assays, supporting quantitative or qualitative tracking of synthetic incorporation in complex samples such as peptide mixtures or reaction monitoring matrices. Chemical biology and analytical chemistry teams use this reagent to validate sample preparation, confirm identity of fluorinated peptide intermediates, and calibrate detection strategies for D-configured, non-natural amino acid-containing targets.
4. Chemical Biology Probe Design
2,4,6- Trifluoro -D-Phenylalanine is used by chemical biology researchers to construct defined probe scaffolds and labeling-ready peptide segments where a fluorinated aromatic residue provides a stable, information-rich handle. The D stereochemistry and strongly substituted aromatic ring help ensure that probe constructs remain structurally consistent across synthesis batches, enabling reproducible conjugation or incorporation into larger probe molecules. This amino acid analog is particularly relevant when investigators want a non-natural residue that can be tracked analytically and that maintains a phenylalanine-like geometry within the probe design.
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