4-Fluoro-D-Phenylalanine is a fluorinated, non-proteinogenic amino acid derivative featuring a D-stereocenter on the α-carbon and a para-fluoro substituent on the phenyl side chain relative to the amino acid backbone. The molecule contains a free α-amino group and a free carboxyl group, while the aromatic ring bears a fluorine substituent that modulates electronic character and can influence hydrogen bonding and hydrophobic interactions in peptide or ligand contexts. As a fluorinated phenylalanine analogue, it is used in peptide synthesis and structure-activity or binding studies where incorporation of a defined aryl fluorine enables analytical tracking and systematic evaluation of side-chain effects.
CAT No: CP14602
CAS No:18125-46-7
Synonyms/Alias:4-Fluoro-D-phenylalanine;18125-46-7;(R)-2-Amino-3-(4-fluorophenyl)propanoicacid;D-4-Fluorophenylalanine;p-Fluoro-D-phenylalanine;H-D-Phe(4-F)-OH;(2R)-2-amino-3-(4-fluorophenyl)propanoicacid;4-fluor-d-phenylalanin;D-4-FLUOROPHE;UNII-963G7O1PVE;(R)-4-FLUOROPHENYLALANINE;D-PHENYLALANINE,4-FLUORO-;MFCD00063064;PubChem17502;PubChem17965;AC1LEQE0;Lopac-F-4646;4-Fluorophenylalanine,D-;AC1Q4NO3;D-4-F-PHE-OH;SCHEMBL72793;H-P-FLUORO-D-PHE-OH;D-4-F-PHE;KSC174O9L;47318_ALDRICH
4-Fluoro-D-Phenylalanine is a D-configured phenylalanine analog bearing a fluorine substituent on the aromatic ring, making it a stereochemically defined, non-natural amino acid building block for structure-activity and conformational studies. Its aryl fluorine provides a distinctive electronic and steric environment that is widely leveraged in medicinal chemistry and peptide-based research, including workflows where fluorinated amino acids are used to probe binding-site interactions and improve analytical detectability. As a research-grade amino acid, it is typically handled as a defined chiral reagent for incorporation into peptides, peptidomimetics, and synthetic intermediates.
1. Peptide Analogue Synthesis
4-Fluoro-D-Phenylalanine is used by peptide chemistry groups to introduce a fluorinated, D-amino acid residue into peptide analogs and peptidomimetics. The D-configuration supports preparation of stereochemically controlled sequences used to study protease tolerance, backbone stereochemical effects, and structure-activity relationships in peptide-like scaffolds. In custom peptide synthesis and medicinal chemistry programs, the fluorinated phenyl side chain is selected to tune aromatic electronics and to provide a chemically distinctive handle that can be tracked by mass spectrometry and NMR during synthesis verification and analytical characterization.
2. Medicinal Chemistry SAR Studies
4-Fluoro-D-Phenylalanine is commonly employed in medicinal chemistry and chemical biology programs that perform SAR (structure-activity relationship) development on fluorinated amino acid-containing ligands. Researchers use this building block to systematically vary aromatic substitution patterns and stereochemistry to evaluate how ring fluorination and D-amino acid incorporation influence binding-site complementarity and conformational preferences. The defined side-chain fluorine also supports downstream analytical workflows, where fluorinated analogs can be differentiated from non-fluorinated counterparts during LC-MS method development, compound library QC, and comparative profiling of synthetic series.
3. Protein Engineering Probes
4-Fluoro-D-Phenylalanine is used in chemical biology and protein engineering workflows that rely on incorporating non-natural amino acids into peptide or protein constructs for mechanistic studies. Laboratories preparing stereochemically defined protein segments or binding probes use this residue to perturb local structure and aromatic interactions in a controlled manner, enabling mapping of how side-chain electronics and stereochemistry affect recognition events. The fluorinated aromatic motif further supports orthogonal characterization of modified constructs, including targeted MS/NMR readouts that distinguish fluorinated variants from native or unlabeled analogs.
4. Chiral Intermediate Development
4-Fluoro-D-Phenylalanine is also used as a chiral starting material for pharmaceutical intermediate development and specialty synthesis where a fluorinated phenylalanine-derived stereocenter is required. Process and R&D chemists incorporate this defined D-amino acid scaffold into downstream synthetic routes to access fluorinated intermediates for medicinal chemistry libraries, including protected derivatives and coupling-ready fragments used in iterative analog generation. The presence of the aryl fluorine enables consistent differentiation across synthetic batches and supports analytical confirmation of stereochemical integrity during intermediate qualification.
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